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Top 10 attractions in Chicago

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The Art Institute of Chicago
No. 1 of Best Things to Do in Great Lakes Region

The Art Institute of Chicago

8.4
4.7/5
509 reviews
The Art Institute of Chicago was founded in 1879 and moved to its current location in 1893. Its gray-white stone building exemplifies classical Beaux-Arts style and stands as one of the United States' most historic and large-scale art museums. The collection spans millennia and covers all continents, encompassing painting, sculpture, prints and drawings, photography, decorative arts, African art and pre-Columbian American art, with a total of hundreds of thousands of works. It is often called a "museum of all nations." The French impressionist and post-impressionist collection is the highlight here. Beyond masterpieces by Monet and Renoir, Seurat's "A Sunday on La Grande Jatte," Van Gogh's "The Bedroom," Picasso's "The Old Guitarist," and Edward Hopper's "Nighthawks" are all on display. Grant Wood's iconic "American Gothic" is widely regarded as one of the symbols of American culture. The pair of bronze lions flanking the main entrance have stood guard for over a century, serving as both a city emblem of Chicago and a popular photo spot for travelers before entering. The museum also features a modern wing dedicated to contemporary art, architecture, and design collections, with densely packed exhibits worth seeing—plan to spend at least half a day to fully appreciate them.Chicago · 638m from downtown
875 North Michigan Avenue
No. 3 of Best Things to Do in Great Lakes Region

875 North Michigan Avenue

7.8
4.5/5
244 reviews
The architecture of 875 North Michigan Avenue is informed by its expressive structural system and gently sloping façades. This innovative form was designed to efficiently accommodate the variety of uses contained in the building. The gentle inward slope creates optimally-sized floor plans for both the lower parking and office levels and the higher residential floors. Additionally, the tapered form significantly reduces wind loads, allowing for a reduction in the size of structural members. For Chicago's busy streetscape, the building's shape increases the visual verticality of the building; adding perceived height to an already impressively tall tower. The architectural form of the 875 North Michigan Avenue represents a radical departure from established aesthetics of the time. Initially, critics labeled the building as too industrial, but over time it has come to symbolize the gutsy tradition of structural expression in Chicago. It is often characterized as super-rational, logical, and a representation of the machine age of architecture. It exhibits its true structure much in the tradition of bridge construction. These qualities are at the heart of why the building has endured in the minds of so many.Chicago · 2.4km from downtown
360 CHICAGO
No. 2 of Best Things to Do in Great Lakes Region

360 CHICAGO

7.8
4.7/5
67 reviews
360 CHICAGO Observation Deck sits 1,000 feet above Chicago's legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Hancock Center), 360 CHICAGO gives you the opportunity to experience the best views of the Chicago Skyline and Lake Michigan. 360 CHICAGO's concourse level includes an interactive exhibit highlighting the rich history and vibrant cultures that make Chicago diverse and beautiful. Get inspired to explore Chicago beyond downtown through experiences like The City Beautiful and City Neighborhoods. Travel to the 94th floor in 40-seconds on one of North America's fastest elevators and step foot onto the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Experience 360 CHICAGO Observation Deck with panoramic views of the city, lakefront, and four neighboring states. Download the Magnicity App for a guided tour right from your smartphone. The app includes unique facts, stories, and recommendations to further enjoy Chicago. TILT offers thrill-seekers the chance to see Chicago from a one-of-a-kind view. Step onto TILT and peer out of the building through floor to ceiling windows at a 30-degree angle 1,000 feet above Michigan Ave. TILT is Chicago's highest thrill ride. CloudBar serves up iconic Chicago snacks, like Garrett's popcorn, and neighborhood-inspired cocktails with local breweries on tap. CloudWalk takes you on vibrant, joyful walk through Chicago's neighborhoods and makes for the perfect photo op! *TILT is not included in the purchase of your general admission ticket.Chicago · 2.4km from downtown
Grant Park
No. 4 of Best Things to Do in Great Lakes Region

Grant Park

7.5
4.4/5
118 reviews
Grant Park covers approx. 319 acres and is a core cultural landmark in Chicago. In the center of the park is the Clarence F. Buckingham Memorial Fountain, completed in 1927. Its design was inspired by the fountains at the Palace of Versailles but on a grander scale, and after dark, its lights and water jets create a stunning display. The park connects cultural facilities such as Millennium Park and The Art Institute of Chicago. To the south stands the cast-iron sculpture group "Agora" by Polish artist Magdalena Abakanowicz—featuring numerous headless figures scattered across the lawn, it is a signature public art installation in the park. The park is also the main venue for many large annual events in Chicago. Strolling along the lakeshore path, you will see the vast waters ofLake Michiganon one side and the magnificent silhouette of the Chicago skyline on the other, making it a daily destination shared by locals and tourists alike for jogging, picnicking, or just taking a walk.Chicago · 943m from downtown
Willis Tower
No. 7 of Best Things to Do in Great Lakes Region

Willis Tower

6.5
4.4/5
513 reviews
The Willis Tower, formerly known as the Sears Tower, is a high point in the Chicago skyline. The building is currently used as an office building with a total of 110 floors. Tens of thousands of tourists come here every day just to board the 412-meter-high 103-story Chicago Sky Observation Deck to overlook the entire Chicago panorama. 1.103rd floor observation deck, enjoy the city view of Chicago. As soon as you enter the Willis Tower, you will be attracted by the words "Windy City", "Chicago" and "Chicago City" written in English on the wall. Then step into the elevator, and each floor the elevator goes up will display the current floor, the current height, and the buildings with the same height. For example, the 25th floor: the Statue of Liberty in New York, the 86th floor: the Eiffel Tower in Paris, and the 102nd floor: the Empire State Building in New York. When you get out of the elevator to the observation deck on the 103rd floor, you can overlook the entire Chicago city and the skyline across Lake Michigan. 2. A real sense of suspension, a thrilling and exciting experience When you come here, you must not miss the thrilling feeling of standing on the glass roof. In June 2009, the designer added 4 glass roofs, all of which were built on the west side of the building, extending about 1.2 meters to the interior. Standing on the transparent glass balcony, the city street view is unobstructed, but it is frightening. And you can also see the tourists on the rooftop next to it, and it feels like they are hanging in the air. Of course there are people standing on it, some people are squatting on the glass, and some people are even lying on it. 3. The sky is clear in the daytime, and the neon lights are bright at night. During the day, you can feel the openness of the mountains and small mountains. At night, you can overlook the brightly lit night scene of Chicago. It is recommended to arrive at the observation deck 30-45 minutes before sunset, so that you can see the beauty of the alternating day and night.Chicago · 513m from downtown
Skydeck Chicago
2026 Americas 50 - Night Attractions

Skydeck Chicago

6.5
4.8/5
76 reviews
Skydeck Chicago is the breathtaking, thrilling observatory atop the iconic Willis Tower. The highest observation deck in the United States, Skydeck provides views of the city spanning up to four states and 50 miles on a clear day. Skydeck features The Ledge; five glass floor balconies extending 4.3 feet from Willis Tower and made up of three layers of half-inch thick glass laminated into one seamless unit. After an extensive transformation, Skydeck offers a can't miss, one-stop attraction to discover and see all that the city of Chicago offers from an incomparable vantage point. The revamped attraction features a brand-new, lower-level, museum-like interactive experience that celebrates the unique personality, history, neighborhoods, and sites of Chicago.Chicago · 513m from downtown
Navy Pier
No. 1 of Family-friendly Attractions in Chicago

Navy Pier

6.3
4.3/5
343 reviews
Located on the shore of Lake Michigan, Navy Pier has a history of nearly 100 years and is an iconic attraction in Chicago. Navy Pier is very large, it is U-shaped, with plazas and shops in the middle, and a walkway on the side, walking along the walkway, you can enjoy the view of Lake Michigan. At the end of the pier is the confluence of the Chicago River and Lake Michigan. There is a plaza on which stands a large iron anchor, which was given to the Navy Pier by the cruiser Chicago as a memorial. 1. There is a sightseeing cruise at the entrance to the south side of the pier. You can buy a ticket here to get on the boat and enjoy the beautiful scenery of Lake Michigan on the boat. At night, there are many open-air bars and cafés along the promenade of the marina. When you are tired of playing, you can find a place to sit and enjoy the beautiful view of Lake Michigan, sip a cup of coffee or beer, and even look up at the brightly lit Ferris wheel in the night. 2. Surrounding attractions The large playground by the lake, covering an area of 50 hectares, has everything from parks, shops to restaurants and attractions. You can board the Ferris wheel for a panoramic view, or go for a merry-go-round, sky swing, mini golf, and more. The pier also has the Chicago Children's Museum (ChicagoChildren'sMuseum), Chicago Shakespeare Theater (ChicagoShakespeareTheater) and IMAX Theater. 3. Fireworks show From the end of May to the beginning of September, every Wednesday and Saturday, fireworks will be set off here to commemorate the people who once joined the army.Chicago · 2.6km from downtown
Shoreline Sightseeing(Michigan Avenue)
No. 9 of Best Things to Do in Great Lakes Region

Shoreline Sightseeing(Michigan Avenue)

6.1
4.4/5
18 reviews
Explore Chicago's rich history, famous architecture, and breathtaking skyline. Choose from guided Chicago River Architecture Tours, classic sightseeing tours on Lake Michigan, fireworks tours, and more, such as Brew Cruises and Wine Tasting Cruises and Lakeshore Water Taxi. Lakeshore charters also host memorable events, from casual gatherings to corporate meetings. The Shoreline Sightseeing will give you a real Chicago experience!Chicago · 1.4km from downtown
Millennium Park
2026 Americas 50 - Night Attractions

Millennium Park

5.5
4.6/5
596 reviews
Millennium Park is located in the Loop area of downtown Chicago, United States, and is a large urban park that integrates natural views, public art, and modern architectural design. Upon entering the park, one of the eye-catching views is the mirror sculpture Cloud Gate, designed by artist Anish Kapoor. This massive stainless steel sculpture resembles a bean, and its highly polished surface acts like a giant mirror, reflecting the surrounding skyscrapers, blue sky, clouds, and visitors. Another interactive view in the park is the Crown Fountain, designed by Spanish artist Jaume Plensa. This view consists of two glass brick towers approx. 15 m tall, with large screens on the exterior of the towers that continuously display the faces of Chicago residents, showcasing the diverse and friendly side of the city's inhabitants. Especially in the warmer seasons, the fountain area becomes a joyful space for children to play in the water and for citizens to relax, adding a lively atmosphere to the park.Chicago · 777m from downtown
Magnificent Mile
No. 6 of Night Attractions in Chicago

Magnificent Mile

5.4
4.6/5
172 reviews
Magnificent Mileis located in downtown Chicago, Illinois, United States, and is one of the representative commercial districts on the northern section of Michigan Avenue. It extends north from the DuSable Bridge over the Chicago River to Oak Street, featuring a collection of large shopping centers, boutique shops, hotels, restaurants, and numerous historic buildings, serving as an important window into Chicago's city image. Strolling through this district, you can experience the unique charm created by the blend of modern urban commercial vitality and century-old architectural styles. The Wrigley Building, with its white clock tower, features an elegant exterior inspired by the Spanish Renaissance style, while the Gothic-style Tribune Tower appears solemn and imposing, with its walls embedded with important architectural fragments from around the world, each full of historical stories. Together, these two buildings form the iconic entrance view of the Magnificent Mile.Chicago · 1.9km from downtown

Experiences you can't miss in Chicago

Featured Day tours in Chicago

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Chicago Architecture River Cruise
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4.9/5
· 4.7k reviews· 219 booked
Duration: 60–75 mins
Free cancellation
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96.7% of travelers recommend
FromUS$39.00
Best of Chicago: Premium Small Group City Tour
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Duration: 1.9 hrs
English
Free cancellation
FromUS$48.00
Iconic Action Film and Movie Locations 1 Day Tour in Chicago
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Duration: 5.6 hrs
English
Free cancellation
FromUS$123.56
Chicago Mobsters Gangsters Ghosts and Prohibition Tour
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Duration: 24 hrs
English
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FromUS$35.00
Travel Internet Hubby eSIM - USA
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Duration: 24 hrs
English
FromUS$1.12
Chicago Architecture River Cruise
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4.9/5
· 4.7k reviews
Duration: 60–90 mins
English
Free cancellation
Book now for today
96.7% of travelers recommend
FromUS$39.00

Featured Cultural experiences in Chicago

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Chicago CityPASS: 5 attraction admission tickets
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5.0/5
· 1 review· 23 booked
English
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FromUS$146.45
Chicago CityPASS
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4.9/5
· 26 reviews· 213 booked
English
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26 consecutive positive reviews
FromUS$142.36
The Art Institute of Chicago: Fast Pass
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4.3/5
· 4 reviews· 298 booked
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FromUS$39.81
Flyover Experience in Chicago
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Free cancellation
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FromUS$27.82
Medieval Torture Museum: Entry Ticket
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Free cancellation
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FromUS$35.77

Featured Water activities in Chicago

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Chicago: History and Architecture Guided Kayak Tour
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5.0/5
· 4 reviews
Duration: 2 hrs
Free cancellation
Book now for tomorrow
5% off
Limited-time sale
FromUS$60.92US$64.13
Chicago: 2-Hour Downtown Kayak Rental
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5.0/5
· 9 reviews
Duration: 2 hrs
Free cancellation
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5% off
Limited-time sale
FromUS$59.37US$62.5
Chicago in a Day: Food & Walk Tour+Free Bike or Kayak Rental
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5% off
Limited-time sale
FromUS$94.05US$99.01
Chicago: Guided Sunset Kayak Tour on the River
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Duration: 2 hrs
Free cancellation
5% off
Limited-time sale
FromUS$57.00US$60.01
Chicago: Guided Kayak History and Architecture Tour
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5% off
Limited-time sale
FromUS$52.10US$54.85
Chicago: Riverwalk Introductory Kayak Lesson & Paddle
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5% off
Limited-time sale
FromUS$28.41US$29.91
Chicago: Best of Attractions Walking Tour +Bike/Kayak Rental
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Duration: 2 hrs
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5% off
Limited-time sale
FromUS$47.50US$50
Neon Paddle: Motorized Glowing Paddleboard Tours Chicago
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5% off
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FromUS$99.75US$105.01

Free things to do in Chicago

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Group Tours in Chicago

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What travellers say about Chicago

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Pao Caballero12 October 2026
5.0
It’s totally worth it, the collections were gorgeous and engaging. The infrastructure is amazing and a great experience overall. Many things to see and read. Plus all the prestigious artist that have been exhibited in the location.

The Art Institute of Chicago

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YoYo_1I8Q7O5O1 June 2026
5.0
875 North Michigan Avenue was that narrow, black skyscraper, like a block of wood stuck at the intersection. The building was pitch black inside; the elevator doors opened onto glass windows, offering a view of Chicago spread out below. The wind was so strong the windows rattled, and the lake was a hazy, indistinct expanse of gray. A child was pressed against the window counting boats, but forgot to finish halfway through. The distant sound of traffic below drifted up like muffled thunder. Feeling dizzy after standing there for a while, I quickly found the elevator and went down.

875 North Michigan Avenue

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windyxp3 October 2026
5.0
We arrived in a bit of a rush and didn't have time to carefully read the information about the ascent route. The view from the top floor was beautiful; Chicago truly lives up to its reputation as the third largest city in the US in terms of architectural style. There's a bar and gift shop on the top floor, and it was very crowded, making it difficult to find a clear spot for taking photos.

360 CHICAGO

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小思文11 December 2021
4.0
Grant Park is also a good place to visit for free. The most common people you see are locals doing outdoor sports. Running is very popular and can be seen at different times of the day. There are also some people walking their dogs.

Grant Park

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梵菲儿287 May 2026
5.0
Worried about not being able to buy tickets, I bought them online, only to find out later that buying them on-site was cheaper. The scenery here is first-rate, definitely worth the trip. There are some decorations before the elevator, perfect for taking photos 📸, which is quite interesting. Many people arrive before dusk to see both the daytime and nighttime views. Each group has a 2-minute photo time limit; you can queue again if you want to take more photos after that.

Willis Tower

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Travel is good13 April 2024
5.0
Walking on the glass ledge induces an exhilarating mix of awe and excitement, making it a must-try for visitors seeking a unique perspective of Chicago's skyline. Whether you're a tourist or a local, the Skydeck's glass walk is sure to leave you with unforgettable memories and stunning photo opportunities. can see 360 degrees the city and beautiful Lake Michigan

Skydeck Chicago

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RaushanK29 April 2025
5.0
Nice place. This was in winter during Christmas. A lot of fun!!!

Navy Pier

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_TS***s924 September 2022
5.0
My wife and I had a problem with tickets as our flight was delayed and we missed our cruise arrival time. I thought we were out of the prepaid money but I called Shoreline Sightseeing and explained the situation to “Vanessa” at their call center and she immediately helped me. The day/time was rescheduled at no added cost. “Vanessa” was very helpful, friendly, and handled things professionally. We couldn’t have been happier with the Customer Service she extended to us and strongly recommend their services based on that alone. Updates on the cruise forthcoming. Thanks again “Vanessa” for insuring our trip to Chicago was memorable!

Shoreline Sightseeing(Michigan Avenue)

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Sane7147 October 2022
5.0
Nice area to walk around, many things to look at, and the big silver jelly bean lol.. The city just gorgeous as well.. Must return one day

Millennium Park

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莲子9928 October 2020
5.0
Chicago's most important, wealthiest, and most architecturally innovative landscape and financial street, connecting the Hancock Building in the north, the Navy Pier in the middle, the Millennium Park in the south, etc., is a regular travel route.

Magnificent Mile

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Frequently asked questions

What are the must-do things in Chicago?

Don't miss these attractions in Chicago: The Art Institute of Chicago, 875 North Michigan Avenue, and 360 CHICAGO. If you like Day tours, try Chicago Architecture River Cruise. If you enjoy Cultural experiences, try Chicago CityPASS: 5 attraction admission tickets.

When choosing a tour, start with how much time you have and the kind of experience you're looking for. Trending options right now include Chicago Architecture River Cruise, Best of Chicago: Premium Small Group City Tour, and Iconic Action Film and Movie Locations 1 Day Tour in Chicago. Check the real-time availability and itinerary before you book.

As of 13 October 2026, the reference price for day tours and activities in Chicago is around USD 1.12 – USD 123.56. Rates vary by duration, group size, transport, tickets, meals, and any special admission requirements. Before you book, please confirm the billing currency and whether the price is quoted per person or per group.

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Change and cancellation policies vary by attractions and tours. Please check the product details page for more information.

Ticket prices may vary between weekdays and weekends, as well as during peak and off-peak seasons. When booking with Trip.com, you can also use Trip Coins to get extra savings. For more tips on booking discounted tickets, please visit Trip.com for the latest information.