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The Top 28 Things To Do in Downtown Chicago

If you can visit only one neighborhood in the Windy City, make it Downtown Chicago. It’s brimming with a vibrant cultural scene, architectural marvels, huge parks, and top museums. With great dining options and top-notch entertainment, Downtown Chicago is the heart of this unforgettable city.

May 26, 202318 min read

Anecia Ascalon
Anecia Ascalon
Team Building Expert

If you can visit only one neighborhood in the Windy City, make it Downtown Chicago. It’s brimming with a vibrant cultural scene, architectural marvels, huge parks, and top museums. With great dining options and top-notch entertainment, Downtown Chicago is the heart of this unforgettable city.

Experience the best of Downtown Chicago with a visit to these 28 attractions!

1. Chicago River Architecture Cruises

chicago river cruises

Architecture cruises offer a captivating journey through the architectural wonders of Chicago. Lasting around 75-90 minutes, these cruises take passengers along the scenic Chicago River, allowing them to witness the city's skyline and famous buildings up close. Knowledgeable guides provide fascinating insights into the architectural history, design, and significance of landmarks such as the Willis Tower, Wrigley Building, and Tribune Tower. Cruises are a relaxing way to get to know one of the most famous attributes of Chicago and enjoy some fresh air.

2. The Escape Game Chicago

people playing an escape game

Have an adventure day or night at The Escape Game Chicago, where you’ll put your detective hats on to find a way out of a ‘locked’ room in just 60 minutes! Each of their five games has multiple rooms to explore and puzzles that fit the game’s theme. Stop a global catastrophe by apprehending evil forces hiding in a mysterious night market. Break out of a 1950s prison cell or recover a stolen Monet painting from an art thief.

The Escape Game is great for families, adults, and just about anyone who likes a good challenge and a bit of sleuthing. They can accommodate groups, small and large. In fact, it’s a terrific activity for work parties and corporate events in Chicago!

3. 360 Chicago

360 Chicago

For breathtaking 360-degree views of the city and its surrounding landscapes, go to this observation deck on the 94th floor of the John Hancock Center. If being that high up is not enough of a thrill for you, check out TILT, a thrilling attraction that tilts visitors outward from the building, providing a downward-facing view from 1,030 feet up! Looking for less heart-pumping and more heart-thumping? The Signature Lounge on the 96th Floor of the building is a perfect place to go for a romantic date night in Chicago.

4. Art Institute of Chicago

Monet at the Chicago Art Institute

The Art Institute of Chicago is one of the most respected art museums in the world. Make time to see its outstanding collection of Impressionist paintings, the largest outside the Louvre Museum in Paris. There’s so much more to the Art Institute though. The collection has 300,000 pieces of art from around the world, some as old as 5,000 years! See works from the ancient world to modern-day gems. The Institute is a perfect spot to visit on a rainy day in Chicago as it will keep you captivated for hours!

5. Millennium Park

The Bean

Perhaps the most famous attraction in Millennium Park is the Cloud Gate sculpture, also known as "The Bean," made entirely of stainless steel and weighing 110 tons! What makes the Bean so ideal for photographs and selfies is that its surface reflects the city's skyline. The park features beautiful gardens, an outdoor concert venue called the Jay Pritzker Pavilion, and the wildly creative Crown Fountain, which showcases digital faces spouting water. On a hot day in Chicago, the Crown Fountain is an awesome place to splash around and cool off!

6. Maggie Daley Park

Maggie Daley Park

Spanning over 20 acres, the park's design integrates nature and urban elements, providing a picturesque setting with stunning skyline views. There are a variety of recreational activities for all ages. There is a rock climbing wall, a mini-golf course, tennis courts, and a skating ribbon that transforms into a rollerblading track in warmer months. For the little ones, the park features a playground with whimsical sculptures and climbing structures. Maggie Daley Park may be one of the most imaginative parks you'll ever visit!

7. Navy Pier

Centennial Wheel

Navy Pier, along Lake Michigan, is a great place to go, day or night. It spans over 3,000 feet and offers visitors an opportunity to walk along the boardwalk, dine at one of several restaurants and do some shopping. If you aren't afraid of heights, take a ride on the famous Centennial Ferris Wheel and get amazing views of Chicago and Lake Michigan from 200 feet up! Navy Pier hosts lots of entertaining events and festivals. In summer, a fireworks display takes place every Wednesday and Saturday night.

8. Field Museum of Natural History

T Rex at the Field Museum

The impressive Field Museum is one of the largest natural history museums in the world. It houses a vast collection of over 40 million artifacts and specimens, including dinosaur fossils, ancient artifacts, gemstones, and cultural exhibits from around the globe. The spectacular exhibits bring ancient wonders to life. Meet SUE, the largest and most complete T.rex ever discovered! Learn about the evolution of life over 4 billion years. See mummies and gawk at an ancient Egyptian garnet necklace more than 3,400 years old! Your time at the Field will fill you with a greater appreciation of our planet's rich history and biodiversity.

9. Chicago Theatre District

people sitting in a theater

A night out in the Theatre District is a night to remember! The renowned cultural center is known for its high-caliber performances in luxurious landmark theaters like the James M. Nederlander Theatre and the Cadillac Palace. Pick from Broadway shows, plays, concerts, and more. The district has plenty of restaurants so you can grab a bite before or after your show. Plus, there are trendy bars and lounges if you want o stay out late and bask in the nightlife!

10. Riverwalk


Take a stroll on Chicago’s 1.25-mile-long Riverwalk and soak in the energy of the city along the glistening Chicago River. Filled with art installations, eateries, and even free live performances. Don’t miss the Art on The Mart, a nightly light show where artwork is projected onto the massive Mart Building.

11. Chicago Children's Museum

Your kids’ imaginations will be unleashed in this excellent children’s museum located at Navy Pier. The hands-on exhibits will have them building pint-size skyscrapers, searching a fossil pit, and swinging from the ropes in a playground paradise. From science to art, this magical place is one of the best attractions in Chicago for families!

12. Magnificent Mile

Magnificent Mile Sign

Shoppers visiting Chicago gravitate to Magnificent Mile, a stretch of Michigan Avenue lined with upscale retailers, luxury boutiques, and prestigious department stores. But shopping isn't the only thing to do here. The avenue is dotted with examples of Chicago’s extraordinary architecture and historic landmarks.

Walk past the John Hancock Center, the Wrigley Building, and the Chicago Water Tower, which is one of the few structures that survived the Great Chicago Fire of 1871! With hundreds of restaurants and entertainment options, spending time along the Magnificent Mile is one of the very best things to do at night in Chicago!

13. Loop Mural Walk

BB King Mural

Chicago has a remarkable street art scene, so much so that the Downtown Chicago Alliance has created this free, self-guided Loop Mural walk for locals and tourists to use. The walk is split into three routes and assigned a level of difficulty in terms of distance and ease of accessing the murals. The Southern Loop Mural Route is near the Art Institute of Chicago. The State Street Mural Route passes through the Theater District. The Northeast Loop Mural takes you close to the Riverwalk.

14. Soldier Field Stadium

Soldier Field Stadium

Soldier Field was originally built in 1924 as a memorial to American soldiers who lost their lives in World War I and was named in their honor. The original stadium was designed in the Beaux-Arts architectural style, but it underwent a major renovation in 2003 that transformed its appearance.

The renovation aimed to preserve the historic colonnades and façade while introducing a modern interior. The result is a unique blend of classic and contemporary elements. But the architecture isn't the main draw- it's what goes on at the stadium! See the NFL’s Chicago Bears as well as the hottest concerts of today!

15. Second City Comedy Club

This renowned comedy theater and improvisational comedy troupe is famous for launching the careers of numerous comedy legends, including John Belushi, Tina Fey, Steve Carell, Bill Murray, and many others. The Second City showcases a mix of sketch comedy, improvisation, and musical performances, featuring talented comedic actors and writers. Note that most shows are not suitable for teens or children. But if you are looking for things to do in Chicago for adults, the Second City can offer you hilarious and cutting-edge comedy performances!

16. Shedd Aquarium

Shedd Aquarium

From the coral reefs to the majestic beluga whales, every corner of the Shedd is bursting with life. You can witness adorable penguins waddling around, touch stingrays gliding through your fingertips, and even come face-to-face with graceful sharks. With its engaging exhibits, interactive shows, and knowledgeable staff, the Shedd is a place where education and entertainment seamlessly come together.

17. Skydeck

The Ledge at Skydeck

A visit to Skydeck, an observatory located on the 103rd floor of the Willis Tower (formerly known as the Sears Tower) is an exhilarating experience. Your visit begins with a high-speed elevator ride that takes you to the 103rd floor in just 60 seconds. Once you arrive, you step out onto the glass-floored ledge known as "The Ledge," which extends out from the building's façade.

The Ledge allows you to see the cityscape over 1,300 feet below! From the Skydeck, you can enjoy panoramic views of Chicago's skyline, Lake Michigan, and the surrounding area. On a clear day, you can see up to four states. The views are particularly wonderful during sunset and after dark when the city lights up.

18. United Center

From mid-October to mid-April at the United Center, you can see the incredible Chicago Bulls, the team that brought us legends like Michael Jordan, Scottie Pippen, and Dennis Rodman! For a somewhat rougher sport, see the Chicago Blackhawks play hockey. If you don't want to see any sport, no problem! The United Center hosts concerts of the very best popular artists like Pearl Jam, Beyonce, Depeche Mode, Lizzo, and so many more!

19. Adler Planetarium

people watching a space show

Established in 1930, the Adler is the first planetarium in the United States and has played a significant role in popularizing astronomy and space science. With engaging exhibits, immersive shows, and interactive displays visitors can explore the wonders of the universe and learn about celestial objects, space exploration, and mesmerizing views of the cosmos in the state-of-the-art theaters.

20. Chicago Sports Museum

The Chicago Sports Museum serves as a tribute to Chicago's spirited sports culture and its impact on the city's identity. Each exhibit explores the history and achievements of Chicago's sports teams, the Cubs and White Sox (MLB), the Bulls (NBA), the Bears (NFL), and the Blackhawks (NHL). The museum celebrates Chicago’s city's sports teams, legendary athletes, and memorable sporting events with its interactive exhibits, memorabilia, and multimedia presentations. In the Fan Zone, you can test your skills and compete against virtual versions of Chicago sports stars!

21. Chicago Cultural Center

Chicago Cultural Center

The Cultural Center is housed within a Beaux-Arts historic structure that was originally built in 1897 as the city's central public library. The exterior features grand stone facades, while the interior features a breathtaking Tiffany glass dome. It spans 38 feet in diameter and is composed of over 30,000 individual glass pieces, creating a kaleidoscope of colors when sunlight streams through. In addition to its architecture, the Chicago Cultural Center is known for its free cultural events. Stop by --there’s always something happening!

22. Giordano's

deep dish pizza

When in Chicago, you simply must eat deep-dish pizza. You can find it throughout the city, but the place to go in Downtown Chicago is Giordano's. Opened in 1974, Giordano’s has been serving its own take on deep-dish pizza. This indulgent dish starts off with a thick, buttery crust that forms a deep well to hold an abundance of toppings. Giordano's takes it a step further by stuffing their deep-dish pizza with layers of cheese, sauce, and toppings.

The pizza is assembled starting with a layer of dough, followed by a generous amount of mozzarella cheese, toppings of your choice, and topped with another layer of dough. Finally, a rich and tangy tomato sauce is spread on top. The result is a thick, cheesy, and flavorful pizza that requires a knife and fork to eat!

23. Cindy's Rooftop

You don't need to go to the top of a skyscraper to get gorgeous views of Chicago. Cindy’s Rooftop is situated on top of the historic Chicago Athletic Association Hotel and has panoramic views of the city's skyline and Lake Michigan. Cindy’s is an attractive space with a glass atrium and modern decor. The ambiance is relaxed and the menu is creative.

The outdoor seating area is warm and inviting, with lounge chairs, communal tables, and cozy fire pits. The bar is known for its award-winning cocktails, craft beers, and an extensive wine list. Plus, Cindy's Rooftop hosts live music performances, DJ sets, and other special events. Cindy’s is a popular spot for a Girls’ Night Out in Chicago!

24. Museum of Contemporary Art

Museum of Contemporary Art

This cutting-edge art and design museum features innovative exhibitions that explore various themes and mediums, including painting, sculpture, photography, installation, and digital art. The museum's dynamic collection includes works by renowned contemporary artists. The MCA provides visitors with a highly thought-provoking experience!

25. Chicago Theatre

Chicago Theatre

Seeing a show at the Chicago Theatre is much more than a night of entertainment. You’ll be taking in marvelous entertainment in a lavish venue that has been a symbol of Chicago's superb performing arts scene for over a century. Architecturally, the Chicago Theatre is a stunning example of the French Baroque style, with a grand marquee, a terra cotta facade, and intricate carvings.

The most notable feature is its eye-catching vertical sign that reads "Chicago." The theatre seats around 3,600 people, so there is an intimate feel to the venue which makes any performance here extra special. The theatre hosts a wide range of performances, including Broadway shows, plays, musicals, concerts, comedy acts, and special events.

26. American Writers Museum

Since 2017, this museum has drawn literary enthusiasts of American literature. Exhibits highlight the lives and works of prominent American writers from different periods and genres. Step into recreated rooms that replicate the working environments of writers such as Jack Kerouac, Maya Angelou, and Ernest Hemingway. Through interactive exhibits, discover the contributions of American songwriters to the country's cultural landscape. There’s even a children's gallery where little ones are introduced to beloved characters and authors.

27. Clarence F. Buckingham Memorial Fountain

Buckingham Fountain

This splendid fountain inside Grant Park is one of the largest fountains in the world. Built in 1927, the fountain's centerpiece is a massive rococo-style marble structure, featuring intricately carved sea creatures and allegorical figures. In the evenings, the fountain puts on a ‘show’ as colored lights are synchronized with the fountain’s gush of water 150 feet high!

28. Blue Man Group

Are you looking for things to do in Chicago with teens? Take them to see these three, bald-headed, blue-painted dudes that make up the Blue Man Group. The Blue Man Group has gained worldwide recognition entertaining audiences of all ages with their innovative approach to live entertainment that mixes music, comedy, and multimedia. The driving force behind the show is the percussive music. Be warned that things can get a bit messy as paint is part of the show! Anyone seated in the first few rows gets an apron!

For even more ideas, check out our article, 36 Awesome Things to Do in Chicago!

Check out our 2 day Chicago itinerary for suggestions on planning your trip!