39 Best Things To Do In Downtown Chicago, Illinois - Updated 2024

things to do in chicago downtown
| 17 min read

Chicago, Illinois, is a city bustling with life and energy. With its glassy skyscrapers and rocking festivals, this windy city will figuratively blow your mind! But don’t be fooled by its modernity. The city’s art museums have just the right amount of old in their new that continues to amaze locals and travelers alike. When you are done exploring the artsy side of the city, don’t forget to indulge in its diverse culinary scene. The accommodation choices are just as pleasing, especially in the downtown area! From historic hotels featuring timeless elegance to fully equipped Airbnb vacation rentals, the bustling heart of the city is brimming with options. Downtown Chicago is so versatile that there is something for everyone. But don’t be overwhelmed by all these options. Read this article to know about some of the best things to do in downtown Chicago, Illinois.

1. Taste a variety of pizza styles on a walking pizza tour (from USD 69.0)

Known as the “Pizza Capital of the World,” Chicago offers a diverse array of pizza styles, and this tour is the perfect opportunity to savor them all. Led by local guides, you’ll stroll through the city’s iconic neighborhoods, visiting renowned pizzerias and hidden gems alike. Each slice offers a distinct and delightful taste, from classic deep-dish to thin-crust tavern-style and everything in between.

As you savor the mouthwatering flavors, you’ll also learn about the history of pizza in Chicago and the cultural significance of this beloved dish. The tour not only celebrates the city’s culinary heritage but also provides an immersive way to explore the streets and culture of Chicago.

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Downtown Chicago Walking Pizza Tour

Duration: 2 to 3 hours

75 reviews

2. Enjoy a fully immersive experience at the Museum of Ice Cream (from USD 49.29)

things to do in chicago downtown | enjoy a fully immersive experience at the museum of ice cream

Enjoy a fully immersive experience at the Museum of Ice Cream in Chicago, Illinois. Inside the museum, you’ll find a variety of imaginative exhibits, larger-than-life ice cream sculptures, and vibrant installations designed to ignite your senses. Every corner offers a unique and Instagram-worthy experience, from colorful sprinkle pools to candy-filled rooms.

As you journey through the museum, you’ll have the chance to taste delicious ice cream treats and learn about the history and science behind this beloved frozen dessert. The museum also hosts engaging activities and games, creating a joyful atmosphere for families, friends, and ice cream enthusiasts.

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Chicago: Museum of Ice Cream Entry Ticket

Duration: 1.5 hour

104 reviews

3. Check out the free cultural performances at Jay Pritzker Pavilion in Millennium Park

Millennium Park August 2010 1 (Jay Pritzker Pavilion)
Source: Photo by Wikimedia Commons user Michael Barera used under CC BY-SA 4.0

Jay Pritzker Pavilion is one of the best places in Chicago to catch free cultural activities and performances. If you are in the city during the summers, then don’t forget to catch their Summer Music and Film Series and World Music Festivals including Broadway in Chicago, the Chicago Jazz Philharmonic, etc. The massive Jay Pritzker Pavilion is made of stainless-steel structures that frame the stage and stands 120 ft (36 meters) tall above the ground.

Jay Pritzker Pavilion at Millennium Park

Address: 201 E. Randolph Street Michigan Ave. & Columbus Ave. Chicago, IL 60601-6530

Website: Jay Pritzker Pavilion at Millennium Park

Opening hours: 6am - 11pm (daily)

Price: Free

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4. Stroll around Millennium Park

Happy Birthday to ME! Millennium Park established July 16, in 2004.

Posted by Millennium Park on Tuesday, 16 July 2019

Bask in the glory of the American sun and soak in the calming vibe at Millennium Park, a public facility that makes for a popular spot for outdoor activities to do in Downtown Chicago. Enjoy a picnic or indulge in a game or two, marvel at the beauty of nature or luxuriate in the manicured gardens, it makes for an ideal place for all. Not just this, it is also quite an abyss for the architecture and design enthusiast. Head over to marvel at “The Bean” and get tons of pictures clicked. Regardless of the time of year, you’re visiting, you’re likely to find an exhibition, festival, tour, or one of the other activities happening here. It is a classic family-friendly spot, so don’t miss it!

Millennium Park

Address: 201 E Randolph St, Chicago, IL 60602, USA

Website: Millennium Park

Opening hours: 6am - 11pm (daily)

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5. Climb to the top of Willis Tower

Looking North from Willis Tower Skydeck, Chicago, Illinois (9179365233)
Source: Photo by Wikimedia Commons user Ken Lund used under CC BY-SA 2.0

If you’re wondering what to see in Downtown Chicago, you should climb the Willis Tower. It is one of the tallest buildings in the world that gives you brilliant vistas of the sky above and streets below. On a clear day, hike up to the United States’ highest skydeck to get sprawling views of up to four states! Once you are done admiring the steely beauty of Chicago from the top, you can scurry down to its 99th floor. The space is reserved specifically for events. Explore Willis Tower to your heart’s content because no structure captures the city’s architectural marvel and aesthetics like this building.

Skydeck Willis Tower

Address: 233 South Wacker Drive Chicago, IL 60606

Website: Skydeck Ledge Willis Tower

Opening hours: 9am - 10pm (daily)

Price: 25 USD

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6. Admire stupendous views from Willis Tower (from USD 38.25)

things to do in chicago downtown | admire stupendous views from willis tower

Standing proud amidst Chicago’s stunning skyline is the Willis Tower, formerly known as the Sears Tower. Otherwise, an ordinary office building, what makes the Willis Tower such a major attraction is its staggering height and the stupendous views that visitors are able to enjoy from its viewing deck. Towering at a height of a phenomenal 442m (1,450ft) approximately, the building is among the world’s tallest and definitely one of Chicago’s most iconic. Head over to the building and learn amazing facts about its architects, history, and how it came to be the title holders of the world’s tallest building for a solid 25 years. You can climb up the Skydeck, on the building’s 103rd floor, which is still the highest viewing deck in all of USA and marvel at the panoramic views from “The Ledge”, the deck’s main attraction, which is a glass balcony that the visitors can climb onto and admire views from a height of about 412m (1,353ft)! Quite thrilling and definitely a must-visit.

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Chicago: Willis Tower Skydeck and The Ledge Ticket

2883 reviews

7. Wander into Chicago's bustling Navy Pier

Navy Pier from the shoreline
Source: Photo by Wikimedia Commons user David Bjorgen used under CC BY-SA 2.5

While there are lots of new things to see in downtown Chicago, Navy Pier remains a crowd favorite. We called Chicago’s Navy Pier home to gaiety and we weren’t kidding. Some of the largest and liveliest events and festivals are hosted here. It can easily be called a landmark and has several eateries and other fun attractions, all for you to enjoy.

Right from an amusement park to yoga and dance classes, musical shows to drama performances, fine dining to zingy street food, there’s everything here. Set against a backdrop of the waterfront, the Navy Pier really makes for a stunning location for outdoor events, which are also regularly hosted here. Do head there for a full-blown amazing experience!

Navy Pier

Address: 600 E Grand Ave, Chicago, IL 60611, USA

Website: Navy Pier

Opening hours: 10am - 10pm (daily)

Price: Free

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8. Explore The Art Institute of Chicago (from USD 35.0)

The Art Institute of Chicago is home to some excellent impressionist, post-impressionist, modern, as well as contemporary art. Among the various stellar pieces of art, you’ll see here would be those of famed artists, such as Monet, van Gogh, Renoir, Matisse, and Picasso among others. The latest addition to the museum is the Modern Wing, which has impressive graphic and industrial design artworks on display. Go in for this fast pass tour and gain some insightful knowledge about the showcases as well as the lives of the artists who made them. There are also some kid-friendly activities you can have your little ones participate in.

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Art Institute of Chicago Fast Pass Admission in Grant Park

Duration: 3 hours

48 reviews

9. Cruise along Chicago River from Navy Pier

The HDR-files Chicago Evening Skyline (Navy Pier) (6949149201)
Source: Photo by Wikimedia Commons user Bert Kaufmann used under CC BY-SA 2.0

A cruise on the Chicago River from Navy Pier is one of the best ways to explore the night views of the city. Just sit back and relax as you sail through billion city lights. Navy Pier cruises are not just for romantic seafaring. You can also indulge in its adrenaline pumping speedboat tour and thrilling rides. Choose from a list of tours that best suit your taste and explore Chicago in a whole new way!

Navy Pier

Address: 600 E. Grand Avenue, Chicago, IL 60611

Website: Navy Pier cruises

Opening hours: 10am - 8pm (daily)

Price: 40 USD

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10. Check out famous paintings at The Art Institute

lion in front of art institute of chicago
Source: Photo by Flickr user calbeeb used under CC BY-SA 2.0

No trip to Chicago is complete unless you visit the Art Institute. Located in the heart of the city, the Art Institute is one of the greatest art museums in the world and houses an enviable collection that goes far back in time. Known to be the largest and the oldest art institute, this prominent attraction is famous for its curatorial efforts to offer its visitors the best of the best.

The Art Institute

Address: 111 S Michigan Ave, Chicago, IL 60603, USA

Website: The Art Institute of Chicago

Opening hours: 10.30am - 5pm (daily)

Price: 25 USD

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11. Stand atop John Hancock Center to get sprawling city views

Sunset views from John Hancock Center skydeck
Source: Pexels

John Hancock Center is a 100-story building located in the Magnificent Mile district of downtown Chicago. Thanks to its sprawling observation deck, 360 Chicago, you will get the most breathtaking views of the city’s sprawling skyline and Lake Michigan. If that wasn’t enough, you can also take the adrenaline-pumping thrill ride, TILT, a moving platform that will literally tilt you from the 94th floor! 360 Chicago tour has been curated in such a way that it will definitely become one of your most unforgettable memories.

John Hancock Center

Address: 875 N Michigan Avenue, 94th Floor

Website: 360 Chicago

Opening hours: 9am - 11pm (daily)

Price: 22 USD

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12. Take a relaxing walk along Magnificent Mile (from USD 30.0)

Chicago is an easily walkable city and making it so are the many beautiful stretches that provide the best of views and surroundings – the Magnificent Mile is one. It is also a shopping district, so keep your monies ready, shopaholics! This guided walking tour takes you through the history of the street and throws light on the many striking buildings that fall along its way.

You’ll gain some important information on the inspirational architecture of these Gothic-, Parisian-, Neoclassical-, and Art Dec-style inspired buildings along with those made alike newer architectural styles. The tour is about an hour and a half long, so keep that kind of time aside.

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Chicago: Magnificent Mile Small-Group Walking Tour

Duration: 1 hour 30 minutes

20 reviews

13. Deep-dive into marine life at Shedd Aquarium

Shedd Aquarium Front 1
Source: Photo by Wikimedia Commons user Setiawan Soekamto... used under CC BY-SA 3.0

Shedd Aquarium, located in the heart of Chicago, is home to beluga whales, Rockhopper penguins, alligators, turtles, and much more. If you really want to experience life underwater and introduce your kids to the marine world, then this is the place to be! Explore the thriving aquatic animals from around the world and understand how to protect it! Go deep into the underwater world at Shedd Aquarium that has been a part of Chicago’s key attraction since 1930.

Shedd Aquarium

Address: 1200 S Lake Shore Drive Chicago, IL 60605

Website: Shedd Aquarium

Opening hours: 9am - 5pm (daily)

Price: 39.95 USD

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14. Shop till you drop at the Magnificent Mile

20070509 Foot of Magnificent Mile
Source: Photo by Wikimedia Commons user TonyTheTiger used under CC BY-SA 3.0

Chicago’s Magnificent Mile is also one of the best places to visit in downtown Chicago if your agenda is to shop till you drop. It is your one-stop guide for all shopping in the city. This iconic strip is packed with history, culture, cafes, and a 94th-floor observation deck. But amongst its many features lies the upscale shopping outlets such as Macy’s, Nordstrom, Saks Fifth Avenue, and many more stylish names that will give you a heartfelt retail therapy.

From its elaborate window displays to some of the biggest names in the fashion industry, the Magnificent Mile is truly a shopper’s delight.

Magnificent Mile

Address: 625 North Michigan Avenue, Suite 401 Chicago, IL 60611

Website: Magnificent Mile

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15. Go back in time at Field Museum

A T-Rex Named Sue - Field Museum
Source: Photo by user Lisa Andres used under CC BY 2.0

The Field Museum, located in Chicago, is one of the largest museums of natural history in the world. The museum houses a collection of 24 million objects that explore all facets of the physical earth, right from its inception. Understand the evolution of plants, animals, people, and cultures at this informative Chicago institution that gives you the best tour of the biological and anthropological world. Take a trip around the world and 4.6 billion years back in time at this comprehensive lakefront museum.

Field Museum

Address: 1400 S. Lake Shore Dr

Website: Field Museum

Opening hours: 9am - 5pm (daily)

Price: 24 USD

Tip from Trip101 local expert



A trip to the Field Museum is great for people of all ages that are interested in natural and human history. Make sure to check out all of the dinosaur skeletons and head over to the Ronald and Christina Gidwitz Hall of Birds, my personal favorite exhibit. With a multitude of exhibits to explore, this museum can keep you occupied for a full day and makes for a great rainy day activity!

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16. Explore the interactive Museum of Science and Industry

Interior view - Museum of Science and Industry (Chicago) - DSC06895
Source: Photo by Wikimedia Commons user Daderot used under CC0

Chicago’s Museum of Science and Industry celebrates curiosity. Take a guided walk around the Moon and German U-boats, watch informative science movies in its Giant Dome Theater, explore the Numbers in Nature exhibit, and do lots more. You can also visit the Yesterday’s Main Street exhibit that recreates Chicago Street from 1910 tand quite literally takes you back in time. Once you are done exploring the exhaustive museum, you will certainly feel enlightened and overwhelmed with all the new information.

Museum of Science and Industry

Address: 5700 S Lake Shore Dr, Chicago, IL 60637

Website: Museum of Science and Industry

Opening hours: 9.30am - 4pm (daily)

Price: 21.95 USD

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17. Eat the best food on the Chicago River North food tour (from USD 64.0)

On this culinary walking tour of Chicago, you will get the best taste of this city’s very own cuisine. Just walk through narrow downtown streets with your guide as you learn about Chicago’s food and gain VIP access to popular restaurants in the city. Eat some of the finest foods and see some major Downtown Chicago landmarks as you explore five food tastings!

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Best in Chow: Chicago River North Food Tour

Duration: 150 to 180 minutes

4 reviews

18. Tour McCormick Bridgehouse & Chicago River Museum

Posted by McCormick Bridgehouse & Chicago River Museum on Monday, 28 August 2017

Spread across five floors is the McCormick Bridgehouse & Chicago River Museum, which celebrates Chicago’s river and movable bridges. While the ground level is the Chicago River itself, it climbs up five floors showcasing Chicago’s journey into becoming one of the largest metropolitan towns in the USA.

There are historic maps, photographs, newspaper articles, and several other exhibits that make the trip enriching. Here, you’ll even get an insider’s preview into the workings of the bridge house’s massive machinery. Visit this museum is among the cheapest things to do in downtown Chicago, Illinois, so don’t miss it!

McCormick Bridgehouse & Chicago River Museum

Address: 99 Chicago Riverwalk, Chicago, IL 60601, USA

Website: McCormick Bridgehouse & Chicago River Museum

Opening hours: Thu: 12pm - 7pm; Fri - Mon: 10am - 5pm (closed on Tue & Wed)

Price: 5 - 6 USD

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19. Enjoy fun rides at Chicago Children's Museum

Where else can you play with a 6-foot bass drum? #ChicagoChildrensMuseum

Posted by Chicago Children's Museum on Friday, 10 May 2019

Located on Chicago’s historic Navy Pier (covered later), the Chicago Children’s Museum is spread across three floors and has more than 13 open exhibits. Take your little ones to the Tinkering Lab and let them work with real equipment and tools to create products and develop ideas. Else, there’s the Art Studio where they can get their hands dirty, doing some arts and crafts. The Sound Playground and Treehouse Trails also provide for pretty interesting activities that children can indulge in. There are activities for kids of all age groups here, so don’t forget to stop by.

Chicago Children's Museum

Address: 700 E Grand Ave, Chicago, IL 60611, USA

Website: Chicago Children’s Museum

Opening hours: Mon - Wed: 10am - 5pm; Thu: 10am - 8pm; Fri - Sun: 10am 7pm

Price: 13.95 - 14.95 USD

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20. Visit the exceptional Richard H. Driehaus Museum

What an eye! When the museum first opened to the public in 2008, the renowned architectural photography firm, Hedrich...

Posted by The Richard H. Driehaus Museum on Saturday, 18 May 2019

The Richard H. Driehaus Museum or just Driehaus Museum is an architectural design enthusiast’s paradise. Preserving the relics of the American Gilded Age and the Art Nouveau era beautifully in its permanent and temporary exhibits, the museum’s elegantly furnished interiors are a testament to the most celebrated designers of the 19th and 20th centuries. Built originally as a palatial home for a wealthy American businessman, the museum was designated a Chicago landmark status in 1977 and sees many tourists visiting it to admire the richness and near-perfect restoration of the interior.

Richard H. Driehaus Museum

Address: 40 E Erie St, Chicago, IL 60611, USA

Website: Richard H. Driehaus Museum

Opening hours: Tue - Sun: 10am - 5pm (closed on Mon)

Price: 10 - 20 USD

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21. Explore the American Writers Museum

Posted by American Writers Museum on Tuesday, 14 November 2017

The American Writers Museum is a celebration of literary works and their writers. Although modest in size, the museum throws light on the phenomenal works of various writers across the ages. While the Nation of Writers hall brings American literary history to the fore, the Readers Hall features theories of writing entities on wall text. The children’s gallery, too, is a cosy space to enter into with couches and banners adorning its interior along with the much-loved illustration books and other children’s books.

American Writers Museum

Address: 180 N Michigan Ave, Chicago, IL 60601, USA

Website: American Writers Museum

Opening hours: 10am - 5pm (daily)

Price: 8 - 12 USD

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22. Tour the fabulous Pritzker Military Museum & Library

Have you stopped by our D-Day +75 exhibit recently? We recently did a refresh to the exhibition, adding 2 new videos to...

Posted by Pritzker Military Museum & Library on Wednesday, 24 July 2019

Making for a unique experience is the Pritzker Military Museum & Library, aimed at spreading information about military history and detailed research on it. It is housed on the beautiful Monroe Building’s second floor and welcomes everyone to sneak a peek into the major contributions of the citizen-soldier in American history. While the museum has some great archival exhibits, the library has more than 65,000 books, covering all periods of history, countries, and basically every subject you could think of.

Pritzker Military Museum & Library

Address: 104 S Michigan Ave, Chicago, IL 60603, USA

Website: Pritzker Military Museum & Library

Opening hours: Mon & Fri - Sat: 10am - 4pm; Tue - Thu: 10am - 6pm; Sun: 12pm - 4pm

Price: 5 USD

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23. Visit the Charnley-Persky House Museum

On July 27, SAH will host an open house at Charnley-Persky House in celebration of our 79th anniversary. Please join us...

Posted by Charnley-Persky House Museum Foundation on Tuesday, 18 June 2019

Adding to an already long list of excellent museums in Chicago is the Charnley-Persky House Museum, also known as The James Charnley Residence. What is notable about this museum is that its building design was spearheaded by the famous American architect Louis Sullivan with valuable inputs from another famed architect, Frank Lloyd Wright. The building’s relatively modest exteriors are in sharp contrast to richness the interior exudes. The top-quality woodwork and tasteful adornment with architectural embellishments make the interior quite a sight to behold, while the exterior is a fitting example of modern American architecture.

Charnley-Persky House Museum

Address: 1365 N Astor St, Chicago, IL 60610, USA

Website: Charnley-Persky House Museum

Opening hours: Wed: 12pm - 1pm; Sat: 10am - 1pm (closed on Mon, Tue, Thu, Fri & Sun)

Price: 8 - 10 USD

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24. Explore Chicago Sports Museum

Chicago Sports Museum entrance
Source: Photo by Wikimedia Commons user Briannalelli used under CC BY-SA 4.0

Located along the Magnificent Mile (covered later), the Chicago Sports Museum is a real treat for the sports enthusiasts. Packed with an abundance of interactive exhibits and other exciting experiences related to the Chicago sports scene, the museum combines the best of information, presented in an engaging manner. Right from sports artefacts to personal belongings of famous sportspersons, there’s everything you’ll find on display here.

Chicago Sports Museum

Address: 835 N Michigan Ave, Chicago, IL 60611, USA

Website: Chicago Sports Museum

Opening hours: Mon - Thu: 11:30am - 8:30pm; Fri: 11:30am - 9pm; Sat: 11am - 9pm; Sun: 11am - 6pm

Price: 6 - 10 USD

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25. Tour the unique International Museum of Surgical Science

It's #nursesweek2018 and the IMSS would like to thank nurses around the world for the hard work and care that they offer...

Posted by International Museum of Surgical Science on Wednesday, 9 May 2018

Explore the wondrous world of medicine and the surgical sciences at the International Museum of Surgical Science. Featuring numerous exhibits about the Eastern and Western medicine, the museum’s galleries are divided theme-wise or surgical discipline-wise. Browsing through its alleys, you’ll find photographs, artefacts, medical equipment, and even medical specimens up for display among other things. There’s also a library containing a collection of more than 5,000 books that you can access.

International Museum of Surgical Science

Address: 1524 N Lake Shore Dr, Chicago, IL 60610, USA

Website: International Museum of Surgical Science

Opening hours: Mon - Fri: 9:30am - 5pm; Sat - Sun: 10am - 5pm

Price: 8 - 16 USD

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26. Catch a game at Wrigley Field

Posted by Wrigley Field on Thursday, 12 April 2012

Don’t worry sports enthusiasts, we have something for you too. Built in 1914, the Wrigley Field makes for an essential part of Chicago’s sports scene. It is a baseball park and home ground of the Chicago Clubs team. Offering seating in the two-tier roof decks and the indoor clubhouse along with a fully serviced bar, watching a game at the Wrigley Field makes for a refreshing experience. Check up the team’s website or the field’s Facebook page for the latest game schedule and book your tickets accordingly.

Wrigley Field

Address: 1060 W Addison St, Chicago, IL 60613, USA

Website: Wrigley Field

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27. Catch one of Chicago Symphony Orchestra's concerts

Posted by Chicago Symphony Orchestra on Friday, 5 July 2019

You can’t be in Chicago and not attend one of Chicago Symphony Orchestra’s exceptional performances. Part of USA’s “Big Five” and among the world’s leading symphony orchestra groups, the Chicago Symphony Orchestra has a solid footing in the international music scene. While their home venue is the Orchestra Hall in Chicago, they perform at several other prominent music festivals across the world. Their distinct tones and crystal-clear recordings are a world-class affair, definitely making it one of the most stellar experiences you’ll have in Chicago. Their shows are usually booked out, so remember to make your bookings well in time.

Chicago Symphony Orchestra

Website: Chicago Symphony Orchestra

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28. Enjoy a show at Cadillac Palace Theatre

Posted by Cadillac Palace Theatre on Friday, 23 March 2012

Catch the best of Chicago’s theatre scene at one of the shows being performed at the Cadillac Palace Theatre. Done up in a typical French Baroque style, the theatre has a capacity to seat up to approximately 2,350 guests! It is operated by Broadway in Chicago, a theatre production company, whose troupes stage some of the best theatre performances you’d have ever seen. Keep a tab on their website for the latest showcases and premieres, and remember to book your tickets in advance!

Cadillac Palace Theatre

Address: 151 W Randolph St, Chicago, IL 60601, USA

Website: Cadillac Palace Theatre

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29. Dig into The Chicago Theatre's history (from USD 24.0)

Also a landmark you must include in your to-see lists is The Chicago Theatre and one of the shows being performed there. Having opened its doors in 1921, the theatre has since been a popular venue for movie showcases, stage plays, music concerts, and visual art performances among others. This guided walking tour includes the best of in-depth information about the theatre’s history, architecture, the several historic performances hosted here and access to parts of the building that are otherwise not open to the public. And, once you’re done touring the place, you can also catch one of the performances too!

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The Chicago Theatre Tour Experience

Duration: 1 hour

32 reviews

30. Spend your time leisurely at The Mart

Posted by The MART on Tuesday, 1 November 2016

Also, a landmark in the city is The Merchandise Mart or just The Mart as the locals like to call it. This Art Deco building, located at the Chicago River’s junction, is a leading commercial space where you’ll find some best-kept secrets of the shopping scene in Chicago. The building’s first, sixth, fifteenth, sixteenth, seventeenth, and eighteenth floors have some pretty amazing stores that you can raid. Right from fashion to residential design, these stores cater to clients for everything. And, if not shopping, the building is in itself quite a sight to behold.

The Mart

Address: 222 W Merchandise Mart Plaza, Chicago, IL 60654, USA

Website: The Mart

Opening hours: Mon - Fri: 9am - 6pm; Sat: 10am - 3pm (closed on Sun)

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31. Play mini golf at Maggie Daley Park

We can't think of a better way to end this beautiful weekend than with a round of 18 at City Mini Golf! Open till 8:00 pm tonight.

Posted by Maggie Daley Park on Sunday, 24 September 2017

Also connected to Grant Park is Maggie Daley Park, which is home to one of the best miniature golf courses you’ll find in Chicago. It is an 18-hole course that also has some interesting obstacle additions and other unique features to make the game even more fun. The park is decorated with mini-sized replicas of some of Chicago landmarks, so golfers find themselves aiming for the hole standing right underneath the not-so-towering, pseudo Willis Tower. The course is located towards the southern end of the BP Bridge. Although, do note that the park admission fee and golfing fee may slightly differ.

Maggie Daley Park

Address: 337 E Randolph St, Chicago, IL 60601, USA

Website: Maggie Daley Park

Opening hours: 6am - 11pm (daily)

Price: 3 USD

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32. Check out fabulous exhibits at Chicago Cultural Center

Chicago Cultural Center and Chicago Public Library, Chicago June 30, 2012-42
Source: Photo by Wikimedia Commons user Victorgrigas used under CC BY-SA 3.0

Bringing some of the best cultural performances to the audiences and that too for free is the Chicago Cultural Center, featuring thousands of cultural programmes each year. Right from visual to performing to literary arts, the centre hosts shows for all. Not only are the performances a treat, but also the centre’s building, which is exceptional in all its aspects. The building’s magnificent stained-glass ceilings, palatial lobbies, and sumptuous decoration make it a fitting venue for the rich performances that it showcases. Keep a tab on their Facebook page for the latest line-up and remember to catch one of the shows. Trust us, you’ll not regret it.

Chicago Cultural Center

Address: 78 E Washington St, Chicago, IL 60602, USA

Website: Chicago Cultural Center

Opening hours: Mon - Fri: 10am - 7pm; Sat - Sun: 10am - 5pm

Price: Free

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33. Enjoy recreational activities at Chicago Riverwalk

The Riverwalk comes alive at the stunningly beautiful Riverbank which is the confluence of the three branches of the...

Posted by Chicago Riverwalk on Thursday, 16 August 2018

Spend your time, leisurely strolling around the Chicago Riverwalk and partaking in the many activities that keep happening there. Stretched along the Chicago River, there’s a host of restaurants, cafes, shops, parks, and other fun stuff to do here. While The Marina Plaza has a restaurant, provides outdoor seating, and access to boat rentals, the Cove primarily offers options for kayak and canoe rentals along with a few eateries. If you’re heading to the riverwalk only to enjoy walking or sitting around, The River Theater, The Water Plaza, and The Boardwalk are the place to be. The Jetty also has some fun things to do. Head here and you’ll be able to pack in quite a bit in a single day.

Chicago Riverwalk

Address: Chicago Riverwalk, Chicago, IL 60601, USA

Website: Chicago Riverwalk

Opening hours: 6am - 11pm (daily)

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34. Go sightseeing at Chicago Water Tower

Chicago Water Tower #Chicago

Posted by Chicago Life on Monday, 24 December 2018

Hiding amidst a swarm of towering buildings yet standing out for its iconic Gothic Revival architecture is the Chicago Water Tower, which you must head over to admire. Originally built to serve as a water station for the city, the building houses the City Gallery in the Historic Water Tower now. You can head inside and dig into the works of local photographers and artists that are on display. The tower sits along the Magnificent Mile, so you can easily couple the two trips.

Chicago Water Tower

Address: 806 Michigan Ave, Chicago, IL 60611, USA

Opening hours: 10am - 7pm (daily)

Price: Free

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35. Head to McCormick Place

Posted by McCormick Place on Friday, 17 August 2018

Bordering the shore of Lake Michigan and touted to be North America’s largest convention centre is the McCormick Place, a complex of four interconnected buildings and an indoor arena where some of the largest public events, trade fairs, and other shows are hosted; this is where the Chicago Auto Show takes place. You can easily check up their website and plan to attend one of the ongoing shows. Head there to see the meaning of the word ginormous take shape in the form of the McCormick Place’s sheer size, amenities, and facilities.

McCormick Place

Address: 2301 S King Dr, Chicago, IL 60616, USA

Website: McCormick Place

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36. Admire the beauty of Chicago from a helicopter (from USD 155.0)

Nothing screams awesome more than a helicopter ride above Chicago’s formidable skyline and landscape. Lasting about 12-15 minutes, this tour offers some of the best views of towering skyscrapers of the city and the expansive cover of the water bodies. While you soak in some fantastic views, the pilot will also be providing a commentary of information about the many buildings in your sight and the city on the whole. Quite a unique experience, this one.

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Chicago Helicopter Tour

Duration: 12 to 15 minutes

11 reviews

37. Check out the green spaces at Garfield Park Conservatory

Drinking in all the rain. #Tulips and #muscari in the Artist’s Garden getting ready to give us a big show. #SeeAtGPC #grapehyacinth #thinkspring #natureinthecity #?

Posted by Garfield Park Conservatory on Friday, 19 April 2019

Truly, the open areas in Chicago are stunning, but taking that a notch higher is the Garfield Park Conservatory, one of USA’s largest greenhouse conservatories and home to some of the most exquisite flora exhibits. Rife with diverse plant species and cycads that are more than 2,000 years old, the conservatory is refreshing and invigorating for the eyes, lungs, and the whole being. The Garfield Park Conservatory regularly hosts showcases of new arrangements and light-and-sound shows, which you can easily attend. Both the indoor as well as outdoor gardens and their landscaping are a visual, educational as well as aesthetic delight, so you must NOT miss it for anything.

Garfield Park Conservatory

Address: 300 N Central Park Ave, Chicago, IL 60624, USA

Website: Garfield Park Conservatory

Opening hours: Thu - Tue: 9am - 5pm; Wed: 9am - 8pm

Price: Free

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38. Explore the gangster past of Chicago (from USD 49.0)

While Chicago is usually a safe city for the locals and tourists, there’s a lurking grey area in the city. Head forth this one and a half-hour tour and learn Chicago’s historical connection with a gangster past and a rampant crime scene at one point. The tour is guided by a docent who enlightens you with some very interesting yet freaky details about Chicago’s past. The tour is conducted in a luxury air-conditioned coach with participants being allowed to get off at certain points and explore the area for themselves. There’s also a shorter tour variant available for the time-pressed travellers, so opt-in for that if an hour and a half don’t work for your itinerary.

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Chicago Criminals, Mobsters and Gangsters Bus History Tour

Duration: 90 to 120 minutes

2343 reviews

39. Cruise on the Chicago River (from USD 53.0)

What is there to do in Downtown Chicago, you ask? If not the birds-eye view, enjoy views from the waterfront. One hour and fifteen minutes long, the cruise ride and the on-board commentary provides some valuable insight into the varied architecture of Chicago’s buildings. Right from the John Hancock Centre to the Willis Tower, the tour covers a total of about 40 buildings and their architecture.

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Chicago Architecture River Cruise Guided Tour

Duration: 1 hour 15 minutes

12461 reviews

Explore the best of Chicago

Chicago is a city blessed with versatility and pulsating energy that attracts locals and tourists alike. With the multitude of activities in Chicago, one can easily feel overwhelmed and miss out on must-do recreation. So use this list as your reference point and be sure to experience everything that this city has to offer!

Frequently asked questions about the best things to do in downtown Chicago, Illinois

  • What are the best things to do in Downtown Chicago with kids?

    The little ones will similarly enjoy the trip to downtown Chicago as it allows them to: i) enjoy a fully immersive experience at the Museum of Ice Cream, ii) wander into the bustling Navy Pier, iii) deep-dive into marine life at Shedd Aquarium, and iv) try the fun rides at Chicago Children’s Museum.

  • What are the best places to visit in Downtown Chicago?

    Any visit to Chicago would not be complete without setting foot in these top attractions and landmarks: i) Millennium Park, ii) Willis Tower, iii) Navy Pier, and iv) Magnificent Mile.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Kanika Gupta, from New Delhi, India, is a passionate traveler driven by a quest for knowledge about the world. An avid reader, when not on the road, she immerses herself in books to expand her...Read more

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