From the soaring heights of its iconic skyscrapers to the reflective depths of its public sculptures, the Windy City offers an architectural tapestry unlike any other in the United States. Chicago is a living museum where the legacy of Frank Lloyd Wright meets the modern marvels of the 21st century.
Visitors often find themselves overwhelmed by the sheer density of history and culture packed into the city’s distinct neighborhoods. Whether you are walking along the Chicago River or exploring the Loop, there is a story waiting around every corner.
Understanding the significance of these structures enhances any visit, turning a simple sightseeing trip into a rich historical journey. This guide aims to highlight the must-see icons that define the city’s skyline and spirit.
From family-friendly attractions to architectural feats of engineering, the diversity of landmarks ensures there is something for every type of traveler. These sites are not just photo opportunities; they are the beating heart of the city’s identity.
We have curated a comprehensive list of the most significant destinations to help you plan a memorable itinerary. Each location offers a unique perspective on why Chicago remains a global destination for art, history, and innovation.
Exploring these sites provides a deeper appreciation for the city’s resilience, especially following the Great Chicago Fire of 1871. The city rebuilt itself with ambition, resulting in the birthplace of the skyscraper.
Before you map out your route, it is helpful to understand the layout and history of these attractions. The following list serves as the definitive starting point for your exploration of the Windy City.
Skydeck Chicago
| Address | 233 S Wacker Dr, Chicago, IL 60606 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 9:00 AM – 8:00 PM Tuesday: 9:00 AM – 8:00 PM Wednesday: 9:00 AM – 8:00 PM Thursday: 9:00 AM – 8:00 PM Friday: 9:00 AM – 8:00 PM Saturday: 9:00 AM – 9:00 PM Sunday: 9:00 AM – 8:00 PM |
| Phone | (312) 875-9447 |
Great experience for all ages. Lots of history and culture about Chicago. Tons of photo opportunities. An all around good time. No real wait to get into the exhibit but there is about a 30 minute wait for The Ledge, depending on how many people there are.
One of the best experience in Chicago.
Skydeck Chicago is a must visit.
The view is just woww, and the open viewpoint is just amazing.
Best point to witness golden hour and lake michigan.
Skydeck chicago has good number of restaurants at lower levels. Good seating place to chill.
I would recommend buying tickets in advance and if you are visiting for the first time its better to buy city pass because you can get express entry to elevators.
Willis tower was once the tallest building in the world for 25 years. Top level observation floor is all windows including the ledge. The ledge are large all glass sections that portude out of the building walls. Dare to step into one of these. The sensation is incredible.
The ride on the elevator is so fast you can feel your ears pop on the way up. I say that it is worth the money for all there is to experience if you have never been up on the observation deck.
Plenty of views to go around to take all the photos you want. The fact is the Willis tower is so tall, the other buildings look short looking down on them. There is an unobstructed view all around.
Highly recommend everyone go and see. Experience it even if just once in a life time. Make it one of your life buckets.
Due to unrelated issues, I was late for my 8pm dinner reservation and if I don't know what time the reservation was for I wouldn't have know that I was late due to the professionalism, personally, and excellent customer I had the pleasure of experiencing during my evening dinner! My birthday meal went off without a hiccup, the wait times were not excessive, and the food was delicious! I was pleasantly surprised with the birthday gifts I received, which are worthy of day-to-day use and the button is going in my scrapbook! Highly recommend this experience, especially since at the end of your meal you basically get to go out on the ledge without the hustle and bustle of the crowds giving you your own VIP experience!!!
Visiting the Skydeck Chicago was one of the highlights of our trip! The views from the top are absolutely breathtaking, offering a stunning 360-degree look at the city and beyond. Standing on The Ledge was an unforgettable experience and definitely worth it for the incredible photos.
The staff was friendly and organized, and the entire experience was well-managed from start to finish. If you're visiting Chicago, the Skydeck is a must-see attraction. I highly recommend it to anyone looking for amazing views and a memorable experience!
Clarence F. Buckingham Memorial Fountain
| Address | 301 S Columbus Dr, Chicago, IL 60605 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | — |
| Phone | (312) 742-3918 |
Such a beautiful fountain and a fun stop while visiting Chicago! I especially wanted to see it because I remembered it from the opening of Married… with Children, so it was really cool seeing it in person. The fountain and the views around it are beautiful and definitely worth a quick stop and a few pictures.
The main attraction here is undeniably the fountain display itself. It’s absolutely beautiful, mesmerizing to watch, and makes for a fantastic backdrop if you’re looking to relax or snap a few great photos.
A few practical tips for your visit:
Parking: Street parking was surprisingly plentiful and stress-free, which is a massive win for a busy spot.
Seating Warning: Avoid the bench directly next to the trash bins. We spotted a mouse scurrying nearby, so definitely claim a spot a bit further away from the refuse area.
The Ice Cream Trap: Be cautious of the ice cream truck parked right out front. We got totally bamboozled and ended up dropping $14 for two tiny ice cream bars. Grab your treats elsewhere before arriving to save your wallet.
Despite the sneaky expensive treats and the little uninvited furry visitor by the trash, the park and fountain display are well worth the visit. Just keep your eyes open and enjoy the show!
Buckingham Fountain was one of the highlights of our visit to Chicago. The fountain itself is absolutely stunning and much larger than I expected. The water displays are beautiful to watch, especially with the city skyline serving as a backdrop. The surrounding gardens and walking paths are well maintained, making it a great place to stroll, relax, or take photos.
We visited during Pokémon GO Fest and were impressed by how well the area handled the large crowds while still feeling clean and enjoyable. The views of Lake Michigan and downtown Chicago are incredible, and there are countless opportunities for great pictures. Whether you’re a tourist or a local, Buckingham Fountain is definitely worth a stop while exploring the city.
This was a must do thing for me📷 since growing up my father was a big fan of married with children n watched it on repeat with his hand in his pants like bundy n I remember this fountain in the opening credits!!! My husband was also a big fan of the show as well! Outside of that I'm a fountain fan too!! I just love this one, it's big n beautiful n the longer I looked around the more I saw!! We went back a few times to see this fountain during our 4 day stay🩵 they had chairs out at sunset one night which was pretty nice to sit n enjoy the sunsetting with the fountain!!
Beautiful fountain the surrounding if this fountain are also wonderful. Good walking track with Greenery and you can have a beautiful Chicago downtown view from here. Also lot of attractions nearby like Art museum, planitorium and Art institute
Millennium Park
| Address | Chicago, IL 60602 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 6:00 AM – 11:00 PM Tuesday: 6:00 AM – 11:00 PM Wednesday: 6:00 AM – 11:00 PM Thursday: 6:00 AM – 11:00 PM Friday: 6:00 AM – 11:00 PM Saturday: 6:00 AM – 11:00 PM Sunday: 6:00 AM – 11:00 PM |
| Phone | (312) 650-8298 |
Millennium Park is a must-visit when you’re in Chicago! We had a wonderful time walking around the park and enjoying the beautiful city views. The atmosphere was lively, with lots of people, great photo spots, and plenty to see and explore.
Of course, Cloud Gate (The Bean) is the highlight and makes for some amazing pictures. The park is beautifully maintained and offers a great mix of art, architecture, greenery, and Chicago’s downtown energy.
We really enjoyed our visit and would highly recommend Millennium Park to anyone visiting Chicago, especially for the first time.
Definitely a place you should experience!
Millennium Park is one of those places that absolutely lives up to the hype. Even if you’ve seen photos a hundred times, walking through the park in person is a completely different experience. It’s incredibly well maintained, easy to navigate, and packed with iconic Chicago landmarks all within a few blocks.
Of course I had to visit Cloud Gate, “The Bean,” and it was every bit as impressive as expected. The reflections make for some amazing photos, but there’s so much more to explore. The gardens, public art, fountains, and skyline views make it easy to spend a few hours here just wandering. The atmosphere was full of tourists and locals alike, which made it feel like the heart of the city.
The park is very walkable and connects easily to other downtown attractions, making it a perfect stop whether you’re visiting Chicago for the first time or returning. I visited during the summer and there was always something happening nearby, from people relaxing on the lawn to live performances and street musicians adding to the experience.
If you’re planning a trip to Chicago, Millennium Park deserves a spot at the top of your itinerary. It’s clean, beautiful, free to visit, and one of those places that perfectly captures the energy of the city. I left with some of my favorite photos from the trip and would absolutely come back.
Love this park! So many trees, little pop up shops, snacks, the views are amazing! I couldn't get enough! Loved visiting the bean n other statues n art work in the park! It's a nice place to walk thru, grab a snack n a drink, have a picnic, enjoy the sights! They did well creating this park!
Millennium Park exceeded all my expectations and is easily one of the best attractions in Chicago. From the moment I arrived, I was impressed by how clean, vibrant, and beautifully maintained the entire park is. The iconic Cloud Gate ("The Bean") is absolutely stunning and provides amazing photo opportunities from every angle. Seeing the city skyline reflected in its mirror-like surface is a unique experience that shouldn't be missed.
The park offers much more than just The Bean. Walking through the lush gardens, enjoying the peaceful fountains, and admiring the incredible public art installations made for a relaxing and memorable visit. The architecture surrounding the park is breathtaking, creating a perfect blend of nature and urban beauty. If you're lucky enough to visit during one of the free concerts or cultural events at the Jay Pritzker Pavilion, the experience becomes even more special.
The park is family-friendly, wheelchair accessible, and conveniently located within walking distance of many of Chicago's top attractions, restaurants, and shopping areas. There are plenty of places to sit, unwind, and simply enjoy the atmosphere. Whether you're visiting for the first time or returning again, Millennium Park offers something new to appreciate every time.
I highly recommend setting aside a few hours to fully explore the park. It's a perfect destination for sightseeing, photography, relaxing, and experiencing the heart of Chicago. Without a doubt, this is one of the city's most iconic landmarks and a place I would happily visit again.
Millennium Park in Chicago is an amazing place to visit! The park is beautiful, clean, and full of things to see and do. The Cloud Gate sculpture (the Bean) is a must-see and makes for some great photos. Walking around the gardens, enjoying the architecture, and taking in the energy of downtown Chicago was an unforgettable experience.
It’s a perfect spot for families, couples, or anyone wanting to relax while surrounded by the city’s beauty. There are plenty of great views, nearby restaurants, and attractions within walking distance. A true Chicago highlight that everyone should experience!
Cloud Gate
| Address | 201 E Randolph St, Chicago, IL 60602 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | — |
| Phone | — |
Visited Cloud Gate over the weekend with my family, and it was a memorable experience. The place was quite crowded, as expected, but it still had its own unique charm and vibe that made the visit special.
The reflection of the skyline on the “Bean” is truly stunning, and it’s a great spot for photos and spending time together. Despite the rush of people, the atmosphere felt lively and full of energy, which actually added to the experience.
A must-visit landmark in Chicago, especially if you’re exploring the city with family.
Cloud Gate is an incredible sculpture and much more impressive in person than you might expect. Its huge size, unique shape, and amazing reflections create a fantastic effect. The surrounding area is also beautiful, and it's definitely worth taking a walk through Millennium Park and along Michigan Avenue.
Overall, downtown Chicago is absolutely fantastic. I love coming back to this city every time!
Cloud Gate is one of Chicago’s most iconic landmarks and a must-visit for anyone exploring the city. The mirrored sculpture creates amazing reflections of the skyline, making it a perfect spot for photos, especially around sunset. The atmosphere is always lively, with people from all over the world enjoying Millennium Park. Every time I visit, I discover a new perspective. A true Chicago classic that never gets old!
Visiting Cloud Gate, better known as The Bean, was one of the highlights of my trip to Chicago.
The sculpture is absolutely fascinating. Its polished stainless-steel surface perfectly reflects the Chicago skyline, the surrounding park, and the people around it, creating a unique and interactive experience.
What impressed me most was how the reflections constantly change depending on where you stand. Walking underneath the arch and seeing the distorted reflections from every angle was both fun and mesmerizing.
The combination of art, architecture, and engineering makes this landmark truly special. As an engineering enthusiast, I appreciated the incredible craftsmanship and precision required to create such a seamless and iconic structure.
Located in Millennium Park, it is the perfect place for photos and to admire the beauty of downtown Chicago.
Overall, a must visit attraction in Chicago artistic, innovative, and absolutely unforgettable.
Cloud Gate, “The Bean,” is one of the most iconic places to visit in Chicago.
I loved seeing how beautifully it reflects the city skyline and surrounding buildings.
It’s a perfect spot for photos and gives a unique experience, especially when you see the reflection from different angles. The area around it is also very peaceful and beautiful.
A must-visit place in Chicago for anyone visiting the city.
The Wrigley Building
| Address | 400-410 N Michigan Ave, Chicago, IL 60611 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 8:00 AM – 6:00 PM Tuesday: 8:00 AM – 6:00 PM Wednesday: 8:00 AM – 6:00 PM Thursday: 8:00 AM – 6:00 PM Friday: 8:00 AM – 6:00 PM Saturday: 8:00 AM – 12:00 PM Sunday: Closed |
| Phone | — |
The Wrigley Building is one of the most beautiful and recognizable buildings in Chicago. The architecture is stunning, especially at night overlooking the river. It has such a timeless, classic Chicago feel and really stands out among the skyline. Definitely worth seeing while exploring downtown.
Immortalized in song and in countless photos, this building is an icon of the earlier days of Chicago. It’s also one of the few famous buildings. I’ve never seen the inside of. Someday I’ll have to rectify that. It’s also somewhat surprising. It hasn’t been converted to residential use like the Tribune Tower across the street.
Standing beneath The Wrigley Building feels like stepping into a piece of Chicago’s soul.
Its timeless beauty reminds me that some places become more than just buildings.
Every detail seems to carry a story, a memory, and a little piece of history.
I’ll remember this view not just for how beautiful it was, but for how it made me feel.
The Wrigley Building is one of Chicago’s most recognizable landmarks, standing at the start of the Magnificent Mile along Michigan Avenue. Built between 1920 and 1924 as the headquarters of the Wrigley Company, the structure is famous for its gleaming white terra-cotta exterior and distinctive clock tower inspired by the Giralda tower in Seville, Spain. The Wrigley Building was Chicago’s first air-conditioned office building, a major innovation for its time. The complex actually consists of two separate towers connected by skybridges, and its clock originally required manual winding.
One of my favorite buildings in Chicago and beautiful area to walk around.
Navy Pier
| Address | 600 E Grand Ave, Chicago, IL 60611 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 11:00 AM – 8:00 PM Tuesday: 11:00 AM – 8:00 PM Wednesday: 11:00 AM – 8:00 PM Thursday: 11:00 AM – 8:00 PM Friday: 11:00 AM – 10:00 PM Saturday: 11:00 AM – 10:00 PM Sunday: 11:00 AM – 8:00 PM |
| Phone | (312) 595-7437 |
We visited Navy Pier in Chicago for the first time, and it was a really nice experience. The evening atmosphere was fantastic, especially during the weekday when people were out enjoying the lake, taking boat rides, walking around, and enjoying the beautiful views.
One of the highlights was the fireworks, which are held on Wednesdays at 9 PM and on weekends during the summer season. Watching the fireworks by the lake made the evening even more enjoyable.
There are plenty of food options, including a food court inside the pier building, so it’s easy to grab something to eat while exploring. For kids, there are also several rides and attractions that run into the evening, with some operating until around 10 PM.
The walk along the lake is beautiful, and the overall vibe is lively and welcoming. You can see people relaxing, enjoying boat rides, having food, and simply spending time by the water.
Parking can be tricky, though. It fills up quickly and can be expensive. We paid around $40 USD for about 3 hours.
Overall, it was an amazing first-time experience. If you’re visiting Chicago, I’d definitely recommend going to Navy Pier in the evening, when the atmosphere is at its best!
Walking all the way to the end of the pier and taking in the view of the lake is just breathtaking.
The cool breeze coming off the lake feels amazing.
Lake Michigan is so massive it honestly feels like an ocean, and the contrast between its emerald-blue water and the city skyline creates such a unique vibe.
There are plenty of shops around the pier, and the beautifully maintained trees and flowers make the whole area feel clean and refreshing.
It’s even more beautiful than I ever imagined.
The Navy Pier is alot of fun, lots of walking, restaurants and bars. You can purchase tickets for lake cruises and the cruises are amazing as you are right up closebtonthe Chicago skyline..beautiful. they have a huge Ferris Wheel to ride. Lots of fun. During the week less crowded..weekend packed.
Perfect place for entertainment, nice and clean. Best spot to look at Chicago from top. Good restaurants. You can explore navy pier for hours. Big food court is good place to hide from heat and from cold weather. We was there with kids, best memories. Ferris wheel is really big, on top of wheel you will see entire Chicago. Highly recommend
Beautiful waterfront destination that is always bustling with energy and activity. Navy Pier has something for everyone, from street performances and great restaurants to boat cruises and the iconic Ferris wheel. It was wonderful to stroll along the pier, enjoy a Ferris wheel ride, and stop along the way to admire the stunning Chicago skyline. The lively atmosphere and beautiful views made it a truly awesome place to visit!
875 North Michigan Avenue
| Address | 875 N Michigan Ave, Chicago, IL 60611 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | — |
| Phone | — |
As a huge architecture geek, the John Hancock Center (now 875 N Michigan Ave) is easily one of my favorite buildings in the world. The observation deck never disappoints! We make it a point to come here every single time we visit Chicago, and no matter how many times we’ve been to the top, I am still struck by the incredible industrial beauty of this city. It is absolutely fascinating to see firsthand how Chicago beautifully rebuilt itself after the Great Fire to become a global hub of design and innovation. If you appreciate incredible structure, history, and stunning views, this is an absolute must-stop!
Amazing observation deck with panoramic views in all directions (north, south, east, and west). I especially loved watching the sunset and seeing Chicago light up in the evening — absolutely beautiful.
Honestly, the extra attractions like the tilted window or paid photo services weren’t that interesting. The real highlight is simply enjoying the views, which are totally worth it on their own.
Enjoying the views of Chicago from the observation deck of this skyscraper is something you should do at least once in your life. Although the price was very high for me, the place is nice and you can have a drink while enjoying that 360-degree view.
Great view. Definitely was crowded around sunset and hard to get a seat. Drinks were good, but a bit pricey. It was fun to relax especially after the crowd left.
As many others have written, this will always be the John Hancock building for us. Just like Willis Tower will always be Sears Tower, even if Sears is basically defunct. Both buildings feature the striking engineering work of Faisal Khan, and the skeletal exterior of the building is unique. On multiple occasions, we’ve considered purchasing a condo in this building, only two change our minds for one reason or another instead, will admire it from the exterior and an occasional visit to some of the attractions located in this 100 story monument.
Willis Tower
| Address | 233 S Wacker Dr, Chicago, IL 60606 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 9:00 AM – 10:00 PM Tuesday: 9:00 AM – 10:00 PM Wednesday: 9:00 AM – 10:00 PM Thursday: 9:00 AM – 10:00 PM Friday: 9:00 AM – 10:00 PM Saturday: 9:00 AM – 10:00 PM Sunday: 9:00 AM – 10:00 PM |
| Phone | (312) 875-0066 |
How can you go to Chicago and not climb to the top of Willis Tower? We visited in early August, 2026. We got our tickets on Viator, but I think they are slightly cheaper directly at the box office.
The entrance was very easy to find, just follow the signs. You go down two flights first, and then take the elevator up.
Before you get to the elevator, there is a little history / experience Chicago interactive museum. It was really interesting. They have a display about the food, the neighborhoods, a little of the architecture, and you can even meet the Obamas!
The elevator is interactive and really fast. The video climbs with you as if you are in the building while it’s being constructed, similar to the Freedom Tower on NYC. When the doors open, you’re at the top. Views are amazing! It is a must do. Pay the money, go at dusk, you’ll love it.
This was a great experience!! I love heights n love tall buildings! This skyline was Soo pretty being my first time to Chicago it was like no other! I loved going on the see thru ledge too!! That was so fun!!! I'll definitely do this again! My husband is scared of heights but he did well up there! He just stayed away from the windows lol. He hated seeing me on the see thru glass but he survived taking a couple pics of me while I enjoyed it 🤣 Great experience! I got this as part of my city pass!! What a great deal!
Definitely worth the visit for the city views! I’ve been to both 360 Chicago and this one, and I’d pick this over 360 Chicago. It was cloudy during our visit, but the views were still beautiful, and we could see 4 states from the observation floor. The 90 seconds on the ledge was plenty of time for a few pictures and that amazing look down at the street from the 103rd floor. Loved that the Ledge was included with our Go City Pass, definitely worth it!
Absolutely worth a visit if you’re exploring Chicago! The Skydeck is located on the 102nd floor, but the experience begins long before you reach the top. The walk to the elevators features fascinating exhibits, fun photo opportunities, and interactive displays that make the wait enjoyable.
Once you step into the elevator, you’re surrounded by an incredible video display on the walls, making it easy to forget you’re even moving. The elevator is so fast that you’re at the top in less than a minute, which is amazing in itself.
When you reach the 102nd floor, you’ll have the chance to step out onto the famous glass ledge. If you’re afraid of heights like I am, my advice is…don’t look down at first! I was terrified and almost talked myself out of it, but I’m so glad I went through with it. Standing out over the city was an unforgettable experience and one of the highlights of our trip to Chicago.
If you’re visiting Chicago, this is an attraction you definitely shouldn’t miss!
Willis Tower is definitely one of those iconic Chicago landmarks you have to see at least once. The building itself is impressive, and the views from the top are amazing. I really enjoyed the experience and getting to see Chicago from a completely different perspective. Definitely worth adding to your Chicago itinerary!
Chicago Riverwalk
| Address | Chicago, IL 60601 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 6:00 AM – 11:00 PM Tuesday: 6:00 AM – 11:00 PM Wednesday: 6:00 AM – 11:00 PM Thursday: 6:00 AM – 11:00 PM Friday: 6:00 AM – 11:00 PM Saturday: 6:00 AM – 11:00 PM Sunday: 6:00 AM – 11:00 PM |
| Phone | — |
The Chicago Riverwalk at sunset was one of my favorite parts of the city. I wandered through the area after the architecture cruise on a warm spring evening and absolutely loved the atmosphere. The whole place felt vibrant and alive — people out walking, restaurants and bars full, boats moving through the river, and incredible views everywhere you looked. It’s such a unique way to experience downtown Chicago. The combination of the river, the skyline, and the energy of the city made it memorable. Highly recommend spending time here, especially in the evening.
The Chicago Riverwalk is a beautiful place to walk, relax, and enjoy the amazing views of the city. The river, bridges, and surrounding architecture make the whole area feel lively and special. It’s a great spot for photos, a peaceful stroll, or just taking in the Chicago atmosphere. Definitely worth visiting!
The Chicago Riverwalk is honestly such a vibe! The views of the skyline, river, bridges, and boats make the whole walk feel so uniquely Chicago. There are plenty of spots to stop, chill, take pics, or just people-watch. And the best part? There are restaurants, cafés, and places to grab a bite right along the river, so you can easily turn a walk into a whole afternoon hangout. Definitely a must-do when visiting Chicago!
Loved walking along the Chicago Riverwalk! Such a beautiful way to experience the city, with amazing views of the river, bridges, and incredible architecture. The atmosphere was lively, relaxing, and perfect for taking pictures. Definitely a must-visit when you’re in Chicago!
The Chicago Riverwalk is an absolute must-visit! The views of the city's incredible architecture are stunning, and there's always something to see with boats cruising by and people enjoying the waterfront. It's clean, lively, and filled with great restaurants, bars, and places to relax. Whether you're taking a leisurely walk, grabbing a bite to eat, or just enjoying the skyline, the Riverwalk offers a perfect mix of city energy and scenic beauty. It's one of my favorite spots in Chicago and a place I'd recommend to anyone visiting the city.
Water Tower Place
| Address | 835 N Michigan Ave, Chicago, IL 60611 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 11:00 AM – 7:00 PM Tuesday: 11:00 AM – 7:00 PM Wednesday: 11:00 AM – 7:00 PM Thursday: 11:00 AM – 8:00 PM Friday: 11:00 AM – 8:00 PM Saturday: 11:00 AM – 8:00 PM Sunday: 12:00 – 6:00 PM |
| Phone | (312) 440-3580 |
We wanted to visit Water Tower Mall again bringing back memories from its heyday in the early 1980’s. Glad we did! There’s a pretty neat Lego exhibit on the lower level, too, but beware of the aggressive Lavelier boutique salesperson on the upper level - very aggressive sales tactics with poor BBB reviews.
Water Tower Place is one of our favorite stops in Chicago. It’s a classic Michigan Avenue mall with a great mix of shops, and we always make a stop at the LEGO Store. We also love that the The Ritz-Carlton, Chicago is right there—it’s one of our favorite hotels in the city, and having great shopping downstairs makes the whole experience even better.
It was a treat to be at residential side of water tower at to top floor 👍🥰👏🏻👌✅
We visited the Lego store in Water Tower Place. It had a small display of Legos outside the store to create a car. The store was busy but full of floor support from staff.
Water Tower Place isn't just a mall; it's a curated collection of the most iconic and sought-after stores, restaurants, and entertainment venues, all housed within a structure that's as much a destination as the attractions it contains. The architecture, both inside and out, is immaculate. The exterior brickwork achieves a perfect balance, with colors that enhance its stunning details.
Stepping inside Water Tower Place is akin to entering a museum or a luxurious Italian structure. The space is divine, massive, and opulent, perfectly complementing downtown Chicago's already sterling reputation.
Whether you're a serious shopper or a casual browser, Water Tower Place offers something for everyone. It’s a place where art, architecture, and commerce converge, making it a must-visit destination for anyone looking to experience the best of Chicago.
Flamingo - Alexander Calder
| Address | 210 S Dearborn St, Chicago, IL 60604 |
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| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: Open 24 hours Tuesday: Open 24 hours Wednesday: Open 24 hours Thursday: Open 24 hours Friday: Open 24 hours Saturday: Open 24 hours Sunday: Open 24 hours |
| Phone | (312) 744-2400 |
A must-see landmark in downtown Chicago! The Flamingo sculpture is an impressive piece of public art that stands out beautifully among the surrounding skyscrapers. The bright red color and unique design make it a perfect spot for photos. It’s amazing to see such a famous artwork up close, and the plaza around it is a great place to stop and enjoy the city atmosphere. Definitely worth visiting if you’re exploring Chicago.
Stand in front of this sculpture and be amazed. It was unveiled in 1974 and created by Alexander Calder. There are other examples of public art up and down Dearborn that I encourage you to explore. Picasso, Miro, and Chagall. All of it harkens back to a time when our government valued the communal message of great art.
A really nice spot in the Loop to take a break and enjoy the surroundings. There are several marble benches that make it easy to sit down, relax, and even meet up with friends. The sculpture here is fun and eye-catching, and if you take a closer look, there’s a plaque on the south side that shares a bit of history and background about it, which adds to the experience. What’s interesting is that you’ll find several of these statues spread throughout the Loop, almost like a small outdoor gallery. They bring some character and variety to an area that might otherwise feel dominated by tall, plain high-rises. It’s a good mix of art, history, and a comfortable place to pause in the middle of the busy city.
Alexander Calder's Flamingo, a beautiful Chicago icon, is (in my opinion) the best of Chicago's numerous public sculptures.
It sits in the Federal Plaza, one of the three main public plazas in the Loop. Painted in bright vermillion (a color that's come to be known as "Calder Red"), and standing 53 feet tall, it's hard to miss. Its swooping, curved form contrasts nicely with the rectilinear, black, modernist Mies van der Rohe Federal Center.
The plaza sees a nice amount of foot traffic during the work week. On the weekends it's taken over by a handful of skateboarders and stray tourists.
The Flamingo is every bit as iconic as "Cloud Gate", aka the Bean. But it's far less crowded, easier to walk around, and under, and makes for a much more interesting backdrop for tourist pix.
It's a nice art piece. If you're meeting someone, this statue is in a clean plaza and it's hard to miss this giant thing. There are lots of tourists though, because it's a tourist attraction. You should visit it if you're in Chicago.
The Chicago Theatre
| Address | 175 N State St, Chicago, IL 60601 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 12:00 – 6:00 PM Tuesday: 12:00 – 6:00 PM Wednesday: 12:00 – 6:00 PM Thursday: 12:00 – 6:00 PM Friday: 12:00 – 6:00 PM Saturday: Closed Sunday: Closed |
| Phone | (312) 462-6300 |
I took a group tour of the Chicago theatre on July 17th 2026 at 12:00 PM and our tour guides were amazing! Both tour guides gave us a lot of info about the theatre and the historic venue. They were both very enthusiastic about there jobs and you can tell they love it. I would definitely recommend taking a tour of the theatre as you learn a lot and get to see a lot of cool parts of the theatre you wouldn’t get to see by just going to see a show. The Chicago theater is beautiful on the inside and very clean! When ever I’m in Chicago again I will definitely have to see a show here!
Great venue for a concert. Try a box for a smaller, intimate setting or if you want to just get down with your crew. We sat Box 14 and it was perfect.
Was able to finally see one of my favorite blues legends as the head liner. Not sure what the heck took me so long. He put on a great show for being 90. Go see him if you get the chance.
Chicago Theater is always a good time and doesnt disappoint. Always look forward to seeing a show here.
Attended the Max Amini show at the Chicago Theatre and had an amazing experience! The sound system was excellent, making every joke and moment easy to hear and enjoy. The venue has plenty of space and everything felt well organized. The staff and guides were very helpful in directing people to their seats, which made the whole process smooth and stress-free. Overall, a fantastic venue with great management and a wonderful atmosphere for live shows. Highly recommend!
I cannot explain how wonderful everyone on staff that I interacted with at the Chicago Theater. From security, ticketing, other employees/managers, and ushers everyone was 5 stars.
I'm a part time wheelchair user and it's often difficult to get around these older and beautiful venues and have the option to store my wheelchair and enjoy the show in my seat is rarely available. Not here. Once we got the information of where to enter, a wonderful security guard walked in front of me and cleared the way so I could get through. He was so cheerful and wonderful to speak with. Once I was in the theater, ushers directing traffic made sure to help me find where I'm going and told me what to do. When waiting for the accessible bathroom, the woman took me to the front of the line because there are other bathrooms available, but I'm not able to get to them. My usher made sure I had my chair parked in a safe location, walked me to my seat, and made sure I knew she would get my chair for me if I needed it.
I rarely can speak so highly of venues. There's often a lack of knowledge and miscommunication, but not here. Not even a little bit.
Tribune Tower
| Address | 435 N Michigan Ave, Chicago, IL 60611 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | — |
| Phone | (312) 222-3994 |
My daughter and I happened upon this building as we were walking around Chicago and exploring during her spring break. The building is crazy beautiful and interesting to look at. When we got up close and noticed all the treasures embedded into the outside wall, we were excited to explore them a little closer. I just love history and architecture and what an amazing way to preserve them both in such an awesome way!
The Tribune Tower is one of Chicago’s most famous landmarks because of its beautiful Neo-Gothic architecture and its important role in American journalism. Completed in 1925, the tower was built as the headquarters of the Chicago Tribune newspaper after an international design competition that attracted hundreds of entries from around the world. The building is also known for the unique collection of stones and artifacts embedded in its exterior walls, which were gathered from famous landmarks such as the Great Wall of China and the Parthenon.
Tribune Tower is one of the most striking buildings in Chicago. The architecture is absolutely beautiful, especially when you see it up close along Michigan Avenue. I loved the blend of historic detail and the feeling of old Chicago history tied into the building. One of the coolest parts was seeing the embedded stones and artifacts from famous landmarks around the world built into the exterior — such a unique touch that gives the building even more character.
Is one of those buildings that immediately stands out. The Gothic design feels bold and dramatic, especially compared to the surrounding modern skyline. Up close, the façade details are fascinating, and knowing the building incorporates stones from famous landmarks around the world adds another layer of interest.
Its location on Michigan Avenue makes it easy to admire while walking, and it still carries a strong sense of history and presence. Even with the area being busy, the tower holds its own and feels timeless. A true architectural icon that rewards a slower look rather than just a quick glance.
This building has one of the most impressive exteriors I’ve ever seen 🏛️✨. The design really stands out and immediately catches your attention when you walk by. What makes it even more interesting is the use of blocks sourced from historical sites 🧱📜-it adds so much character and meaning to the structure.
You can really feel the blend of history and modern design coming together in a unique way. It’s not just visually striking, but also thoughtful and symbolic, which makes it even more fascinating to look at 😍. Definitely one of those places that makes you stop and appreciate the details a bit longer than expected 📸💫.
360 CHICAGO
| Address | 875 N Michigan Ave 94th floor, Chicago, IL 60611 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 9:00 AM – 11:00 PM Tuesday: 9:00 AM – 11:00 PM Wednesday: 9:00 AM – 11:00 PM Thursday: 9:00 AM – 11:00 PM Friday: 9:00 AM – 11:00 PM Saturday: 9:00 AM – 11:00 PM Sunday: 9:00 AM – 11:00 PM |
| Phone | (888) 875-8439 |
This was the very first tourist attraction I visited after arriving in Chicago, and I’m so glad I chose it through CityPASS. It was also my first time visiting the city, and honestly, I wasn’t expecting Chicago to be this beautiful. I made a reservation for around 6 p.m. so I could catch golden hour, and it turned out to be the perfect time. I’d definitely recommend booking ahead if you can. The lines weren’t bad at all, and I got up to the observation deck pretty quickly. One of my favorite parts was the CloudBar. It’s such a nice addition because you can grab a drink or a snack while enjoying the incredible views of the river and skyline. The prices are definitely on the higher side, but that’s pretty much what you’d expect at an observation deck like this. I ended up staying much longer than I had planned because I just couldn’t stop looking at the views. This experience honestly changed my perception of Chicago. I had no idea the city was this stunning. Having now visited both Skydeck and 360 CHICAGO, if I only had time for one observation deck, this would be my pick without hesitation. The views were absolutely spectacular and one of the highlights of my trip.
I had planned to get tickets in advance, but I am glad that I had waited because the delay set my friend and I up for a such a beautiful sunset. We did the tilt while we were up there which was definitely worth the experience, but you can’t take pictures in the tilt you can only buy the pictures that the staff takes and those things are wildly overpriced. But all around that level are beautiful views and seats along the windows so you can chill and enjoy the scenery. The elevator ride goes very quickly as well so the whole thing from getting the tickets to waiting for an elevator to open was really only about 15 minutes on a weekday on a beautiful sunset evening.
We visited 360 CHICAGO around sunset, and it was one of the highlights of our trip. Watching the city transition from daylight to sunset and then to a sparkling night skyline was absolutely breathtaking. The panoramic views of downtown Chicago and Lake Michigan are unforgettable.
We also tried TILT, and it was a lot of fun! It may not look intimidating at first, but once the platform slowly tilts you out over the edge of the building, it’s a surprisingly thrilling experience. Definitely worth trying if you’re visiting.
The observation deck was spacious and comfortable, with plenty of room to enjoy the views and take photos without feeling rushed. The staff were friendly, and everything was well organized.
If you have the time, I highly recommend visiting around sunset so you can enjoy both the daytime views and the beautiful city lights after dark.
We absolutely loved coming up here over Labor Day weekend. A beautiful Chicago day! We could see for miles, and the bar up top is absolutely amazing. Fun cute drinks to look over the Chicago skyline. Lots of variety of other non-alcoholic beverages and snacks. A family must do!!!
I visited 360 Chicago on a weekday in July, and it was a great experience overall. It was not busy at all, which made the visit much more relaxing. There was plenty of space to walk around, sit, and enjoy the views without feeling rushed or crowded.
The view was absolutely breathtaking. Since the sky was clear, we got a beautiful view of the city, the lake, and the skyline. It is definitely one of the best places to see Chicago from above. I also felt it was a good use of the C3 CityPASS, especially if you are already planning to visit other attractions in the city.
I also tried Tilt, but honestly, it was not amazing. For the extra price, I did not feel like it was worth it. You are standing on a platform that tilts forward, but it does not give a very exciting or unique experience. I expected it to feel more thrilling than it actually did.
Overall, I would recommend visiting 360 Chicago for the amazing views, especially on a clear day. However, I would probably skip Tilt unless you really want to try it once.
Crown Fountain
| Address | 201 E Randolph St, Chicago, IL 60603 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: 6:00 AM – 11:00 PM Tuesday: 6:00 AM – 11:00 PM Wednesday: 6:00 AM – 11:00 PM Thursday: 6:00 AM – 11:00 PM Friday: 6:00 AM – 11:00 PM Saturday: 6:00 AM – 11:00 PM Sunday: 6:00 AM – 11:00 PM |
| Phone | (312) 742-1168 |
Incredibly fun and family friendly. The diversity of faces makes it feel personal and welcoming. Perfect for cooling off, taking photos, or just people watching. It's free, centrally located near Cloud Gate (The Bean) and integrates beautifully with the park's vibe.
Very nice attraction, perfect to hang out during the summer to have a bit of refreshment.
Perfect spot for families and children.
The Crown Fountain in Chicago is one of those places that perfectly blends art, culture, and fun in a way that feels uniquely Chicago. Located in Millennium Park, it’s not just something you look at—it’s something you experience.
The twin glass towers display ever-changing digital faces of Chicago residents, and every few minutes, they “spit” water into the shallow reflecting pool below. It’s playful and interactive, especially in the warmer months when kids (and honestly, adults too) cool off in the water. At night, the LED-lit towers give the whole space a completely different vibe—more calm, almost mesmerizing.
What makes Crown Fountain stand out is how accessible it is. It’s free, open to everyone, and right in the heart of downtown. You can stop by for a quick visit or hang out for a while and take it all in. It also pairs perfectly with nearby attractions like Cloud Gate (The Bean), making it an easy addition to any Chicago itinerary.
Overall, it’s a must-visit spot if you’re in the city—simple, creative, and memorable without trying too hard.
Crown Fountain in Chicago is an absolute gem. The twin glass towers, the playful water features, and the ever‑changing digital faces make it one of the most unique public art installations I’ve ever visited. It’s fun, refreshing, and full of life—kids splashing, families relaxing, and everyone enjoying the creative energy of Millennium Park. The whole space feels modern, welcoming, and beautifully designed. A must‑see spot that brings art and joy together in the best way.
**Crown Fountain**
A must-see attraction in Millennium Park! Work harder, going about getting down there, real soon, check it out!
**Key Features:**
- Iconic landmark
- Beautiful architecture
- Fun water features
Untitled by Pablo Picasso
| Address | 50 W Washington St, Chicago, IL 60602 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: Open 24 hours Tuesday: Open 24 hours Wednesday: Open 24 hours Thursday: Open 24 hours Friday: Open 24 hours Saturday: Open 24 hours Sunday: Open 24 hours |
| Phone | (312) 744-5000 |
Amazing work that is very large. Little detail to add. Must see in person.
I love it. No one was there outside when i passed around 6pm tuesday. I guess not a lot of people appreciate art? Im not complaining though as i got really good pictures.
Chicago Picasso is a landmark sculpture by Pablo Picasso (1967). Located at Daly Plaza, it is a 15 metre tall Cubist sculpture that from the sides seems to be just fragmented sheets of metal. However, when viewed directly in front, resembles the head of an Afghan Hound.
It is an interesting public artwork worth spending a few minutes to enjoy if you plan to be in the downtown area and enjoy art and monument viewing during your travels.
Cool sculpture in the park.
Love the installation art here! The plaza is also very enjoyable during summer, and Chicago usually has the Christmas market village here during winter. It’s right in the loop and close to millennium park, making it a perfect stop when people come to the loop. (Follow me on IG ➡️ miss_dawang)
Garfield Park Conservatory
| Address | 300 N Central Park Ave, Chicago, IL 60624 |
|---|---|
| Maps | Click here |
| Website | Click here |
| Opening Hours | Monday: Closed Tuesday: Closed Wednesday: 10:00 AM – 8:00 PM Thursday: 10:00 AM – 5:00 PM Friday: 10:00 AM – 5:00 PM Saturday: 10:00 AM – 5:00 PM Sunday: 10:00 AM – 5:00 PM |
| Phone | (773) 638-1766 |
Beautifully designed and meticulously maintained, and definitely worth seeing at least once. The glass structure itself is gorgeous and reminded me a little of the Crystal Palace, and the landscaping throughout is wonderfully manicured. Easily accessible via the Green Line straight from the Loop!
Some of the environments are surprisingly immersive. Walking through the different sections can feel almost Disney-like—in a good way—as though you've suddenly wandered into another climate or even another era. One area in particular gave me this strange prehistoric-desert feeling that I really enjoyed.
And there are plants. Lots and lots and lots of plants. Big plants, little plants, plants everywhere.
Ultimately, though, I realized that conservatories just aren't really my thing. I appreciated the design and craftsmanship of the place more than the actual experience of looking at plants. That's entirely personal preference rather than a criticism of the conservatory itself. If you love plants, gardens, or immersive natural spaces, I can easily imagine spending hours here. I'm glad I visited, but once was probably enough for me.
Garfield Park Conservatory was one of our favorite stops in Chicago. From the moment we walked in, we were amazed by how beautiful and peaceful everything was. The variety of plants, flowers, and trees from around the world was incredible, and every room had something unique to discover. It truly felt like stepping into a tropical oasis right in the middle of the city.
We loved taking our time exploring each section, and there were so many great spots to stop, admire the scenery, and take photos. Everything was well maintained, and you could tell how much care goes into keeping the conservatory looking its best. The walking paths were easy to navigate, and the layout made it enjoyable to wander without feeling rushed.
It was also a wonderful place for families, couples, or anyone looking for a quiet escape from the busy city. Whether you’re interested in gardening or simply appreciate beautiful spaces, there’s something here for everyone.
If you’re visiting Chicago, Garfield Park Conservatory is absolutely worth adding to your itinerary. Admission is affordable, the experience is unforgettable, and it’s a place you’ll remember long after your visit. We had an amazing time and would definitely come back the next time we’re in Chicago.
We loved our visit even though we went on a very hot and humid day. Real feel in the low 100s. It is a green house with beautiful plants from all over! They warned us that they do not have air conditioning. I chuckled since it is a green house to grow plants. They said they needed to tell us because some people don’t realize it isn’t air conditioned. They design is wonderful and we loved taking photos. The fern house has a great game to play where you find figures and little scenes they’ve hidden in the ferns. Take a picture and post it to their Instagram page. Currently they are renovating the front entrance so you enter further north in the building. The temporary path is a corrugated rubber that might be difficult for ADA situations. They do have another entrance further north for wheelchair access during renovations. Locals have great discounts and non locals get discounts for teachers, military and students. Check the website for update tickets and discounts.
The Garfield Conservatory is a peaceful place to spend an hour or two. The gardens are beautiful, well maintained, and there are several different indoor areas to explore. I also appreciated that they have a play area for kids, making it a nice stop for families.
One downside is that there isn’t a gift shop if you’re hoping to take home a souvenir. Also, non-Illinois residents are asked to pay a mandatory $10 donation for admission, which is something to be aware of before visiting.
Overall, it’s a relaxing and worthwhile stop, especially if you enjoy plants and conservatories.
I’ve heard great things about this so finally checked it out with my bf. There’s free parking so that was nice and we bought tickets only for $10 per person which was reasonable. Inside there were different rooms with different plant types like desert, ferns, etc. Some of them had birds in there too! One room had water with fish in it. There was also a place to go outside to explore flowers and the vegetable garden. We went through everything in 40 minutes. I would recommend checking this out at least once!
Tips for Visiting Chicago Landmarks
Navigating a major metropolitan area like Chicago requires a bit of strategy to maximize your time and budget. While the city is highly walkable, the distance between certain landmarks and the variable weather conditions mean that preparation is key. By planning ahead, you can avoid long lines, save money on admission, and ensure you see the city from the best possible vantage points. Here are some practical tips to enhance your sightseeing experience.
Purchase a CityPASS or Go City Pass
If you plan to visit multiple paid attractions, such as the observation decks and museums, an attraction pass can save you nearly 50% on admission. These passes bundle the top sights together, often allowing you to skip the ticket line entirely.
Utilize the Chicago Riverwalk
The Riverwalk is not just a scenic path; it is a functional artery connecting many of the most famous landmarks. Walking along the river is often faster and far more pleasant than navigating the crowded streets above during rush hour.
Time Your Visits to Avoid Crowds
Observation decks like the Skydeck and 360 Chicago are busiest between 11 AM and 3 PM. For the clearest photos and shortest wait times, aim to arrive right when they open or a couple of hours before sunset to catch the transition from day to night.
Dress for the “Windy City”
The nickname is not just for show; the breeze off Lake Michigan can be brutal, especially in the fall and winter. Always bring a light jacket or windbreaker, even if the temperature seems warm, as the wind chill near the lakefront can drop significantly.
Use Public Transit
Driving and parking in the Loop can be expensive and stressful. The ‘L’ train system is an iconic experience in itself and provides convenient access to almost every major landmark listed in this guide. A day pass is usually cheaper than a single hour of parking downtown.
Chicago is a city that rewards the curious. While the famous landmarks draw the crowds, the true magic often lies in the details—the intricate masonry, the public art tucked between towers, and the vibrant street life that surrounds these architectural giants.
As you tick off each site on your list, take a moment to look up and appreciate the engineering marvels that made this city famous. Whether it is your first visit or your fiftieth, the skyline of Chicago never fails to inspire a sense of awe and possibility.
