Chicago boasts impressive building designs, amazing food, beautiful coastlines, and a blend of historic and contemporary culture. With so much to do on your visit, whether this is your first time visiting or you have been before and want to come back for even more fun! The things to do in Chicago have something for everyone: amazing, authentic deep-dish pizza; spectacular performance venues; great views of the lakefront; stunning skyline views; spectacular museums; and a ton of great things to do outdoors! In compiling this complete guide to what to expect from a visit to Chicago, we have included simple descriptions, specific addresses/locations, pricing information, and visitor reviews to help you plan the most enjoyable trip possible.
1. Visit Navy Pier
Price: Free (rides, shows & food extra)
Location: 600 E Grand Ave, Chicago, IL
If you’re looking for something to do while in Chicago, Navy Pier is definitely one of the most popular attractions there. There are so many activities at Navy Pier for people of all ages! While at the pier, take time to walk around, watch boats pass on Lake Michigan, and just enjoy being outside in the nice weather.
Also, if you have time, try to see a few street performers who perform throughout the day on the pier! The Centennial Wheel is located at Navy Pier and offers beautiful views of the skyline, especially when the sun sets! Navy Pier also has many restaurants, beautiful gardens, and seasonal fireworks – adding to the numerous things to do there with friends and family! It’s definitely considered one of the top things to do in Chicago.
2. Eat Deep-Dish Pizza
Price: $15–$30 per person
Popular Spots: Lou Malnati’s, Giordano’s, Pequod’s
Deep-dish pizza is considered an iconic experience when visiting Chicago. The dish has a thick, cheesy base with pie-style toppings. For example, Lou Malnati’s has buttery crusts; Giordano’s focuses on stuffed versions, and Pequod’s has become known for its caramelized edges. The servings usually come in large sizes, so diners often share their pizzas with others. Deep-dish pizza is an absolute must-try things to do in Chicago for every visiter.
3. Walk the Chicago Riverwalk
Price: Free (food & drinks extra)
Location: Downtown Chicago
The Riverwalk in Chicago provides a relaxing experience walking by the Riverwalk and enjoying the surrounding cityscapes at night. The Riverwalk has things to do in Chicago River and also provides an opportunity to see the city’s skyscrapers, bridges, and boats that travel on the river. Travelers can sit on the stairs, enjoy drinks at many of the Riverwalk’s bars, or just take in the ambiance of the Riverwalk. The time of day for travelers enjoying the Riverwalk, particularly the time around sunset, provides for the most peaceful and beautiful scenic things to do in Chicago.
4. Wander Through West Loop
Price: Free (food varies $15–$40)
Location: Fulton Market & Randolph St
With award-winning dining options and a hip, trendy atmosphere, the West Loop neighborhood provides many satisfying activities for foodies and anyone who enjoys exploring neighborhoods in Chicago! While the West Loop was once a collection of industrial warehouses, today you will find a wide variety of shops and restaurants offering everything from scrumptious baked goods to delicious global cuisine. Visitors can also find street art and artisan markets along the streets of the West Loop for a unique and interactive walking experience as they seek out new food experiences. Exploring the West Loop is among the best places in Chicago for enjoyable things to do in Chicago.
5. Try a Chicago-Style Hot Dog
Price: $5–$10
Popular Spots: Portillo’s, Superdawg, Gene & Jude’s
Of the many foods available in Chicago, nothing is more classic things so do in the Chicago-style hot dog – a truly delicious combination of several different toppings (mustard, relish, onions, tomatoes, pickles, sport peppers), but never ketchup! For a first-timer to Chicago, Portillo’s provides an excellent introduction; on the other hand, Superdawg allows one to relive the nostalgic drive-in experience. It’s a quick, delicious, budget-friendly way to check off another iconic activity from your list of things to do in Chicago.
6. The Chicago Theatre
Price: $20–$120
Location: 175 N State
If you’re looking to enjoy the beauty that is The Chicago Theatre, one of our city’s most beautiful landmarks, you won’t be disappointed! The red marquee lit up at night is one of Chicago’s most photographed sites; the interior of the theatre is filled with beautiful French Baroque architecture. Whether you’re attending a concert or comedy show, these things to do in Chicago will make the experience truly amazing! It’s definitely an essential stop for performing arts lovers or anyone who appreciates historic buildings.
7. Watch a Chicago Sports Game
Price: $20–$150+
Teams: Bulls, Cubs, White Sox, Bears, Blackhawks
Attending a sporting event, whether you have a passion for it or want to experience the excitement of what it means to be a part of Chicago, is one of the many things to do in Chicago. The atmosphere of Wrigley Field is outstanding; if you attend a Chicago Bulls game, you will experience high energy from players and fans alike, and you will feel a sense of electrifying excitement at a Chicago Blackhawks hockey match. Even if you do not enjoy sports as much, you should definitely attend a sporting event for the energy and excitement of the crowd!
8. Take Photos at Chicago’s Murals
Price: Free
Neighborhoods: Wicker Park, Pilsen, Logan Square
Chicago is known for its colourful street art, and mural hunting is a great way to see it all. Some of Chicago’s greatest murals are found in Pilsen has large cultural murals, Wicker Park features modern designs, and Logan Square’s “Greetings from Chicago” mural is a traveler favorite. It’s fun, free, and great for photos, which makes it one of the most creative things to do in Chicago.
9. Explore Chinatown
Price: Free (food $10–$20)
Location: Cermak Rd & Wentworth Ave
One of the most enjoyable things to do in Chicago is to tour around Chinatown. You’ll be able to stroll around and see the Chinatown Gate, eat some great dumplings, drink bubble tea, and explore souvenir shops. The area is full of temples, mural artwork, and fantastic downtown streets ideal for spending an afternoon exploring the culture of another country. As such, there are many cultural activities and things to do in Chicago that encompass some of the traditions found all over the world.
10. Enjoy a Comedy Show
Price: $20–$50
Venues: The Second City, Zanies
Because it was the first city to develop improvisational comedy, performing in Chicago is one of the most entertaining experiences available. The Second City has been responsible for the establishment of many well-known comedic talents through its performances. Their shows are known for being fast-paced, funny, and interactive. Zanies, although a less expensive venue, maintains that same comic effect with a more intimate atmosphere. If you want a night filled with laughter, this is one of the most enjoyable things to do in Chicago.
11. Visit the Museum of Science & Industry
Price: $25–$40
Location: 5700 S Lake Shore Dr.
The Chicago Museum of Science and Industry (CSI) is another interactive, educational opportunity in Chicago. At the CSI, you things to do in Chicago, including an actual submarine, aviation exhibits, a weather simulation, and laboratories with real hands-on experiments. Families find this an excellent destination, but adults also love it. With its vast size, you can easily spend several hours in the same building; therefore, it is one of the best indoor things to do in Chicago, especially on rainy days.
12. Shop & Explore the Magnificent Mile
Price: Free
Location: Michigan Avenue
Chicago’s Magnificent Mile is one of the Top 10 Places to Shop, Eat, and See in the city, especially for people who enjoy both shopping and architecture. The elegant street has a great selection of high-end retailers and specialty shops, along with numerous excellent restaurants. People can even enjoy viewing the architecture of the buildings from the outside. This area of Chicago is almost too much fun to visit during the daytime as it is during the nighttime. The illuminated city street is also one of Chicago’s most photogenic things to do in Chicago.
13. Walk Along Lake Michigan
Price: Free
Location: Lakefront Trail
The Lakefront Trail offers fresh air and beautiful views in an ideal place in Chicago, and also offers the ability to walk along the lakefront for miles, where you have unobstructed views of Lake Michigan. This makes it a great spot to bike, walk, or just sit on the grass and enjoy the scenery. The sheer beauty of the sun rising from the Lakefront Trail is breathtaking and one of the best overall things to do in Chicago.
14. Take an Architecture Boat Tour
Price: $40–$55
Location: Chicago River
The skyline of Chicago is known throughout the world, and the best way to see it is with an architecture boat tour, which is informative no matter what your interests are. The guides will tell you about the history of the iconic buildings, including Willis Tower, Marina City, and the Wrigley Building, and you will also be able to see views of the river from a different perspective on this tour. If you are an architect or a photographer, this is one of the most important things to do in Chicago.
15. Visit Skydeck Chicago or 360 Chicago
Price: $30–$45
Locations: Willis Tower & John Hancock Center
360 Chicago and Skydeck Chicago both feature some of the most exhilarating things to do in Chicago. The glass Ledge at Skydeck provides visitors with a chance to actually walk out onto a crystal-clear glass floor that sits high above the street level of the Chicago Loop. However, at 360 Chicago, the TILT will actually tip you out and over the edge of the building so you can see the entire skyline of the city. The views that are offered by both attractions are things that you will never forget, and we suggest visiting either Skydeck or 360 Chicago during sunset to get some spectacular pictures!
16. Join a Murder Mystery Dinner Experience
Price: $60–$120
Location: Various Venues
A Murder Mystery Dinner is one of the best things to do in Chicago for a night of entertainment and engagement. You will be served a complete meal as you work with other guests to solve an imaginary murder case, which includes acting by professional performers. This event is not only entertaining because it is very dramatic and humorous, but it also provides an opportunity for friends and family to participate in something unique and exciting instead of just having dinner together at home or a restaurant.
17. Visit the Chicago Magic Lounge
Price: $35–$85
Location: 5050 N Clark St.
If you like magic, then the Chicago Magic Lounge is a must-see for you because it is one of Chicago’s hidden gems! This bar features incredible close-up magic, entertaining illusions, a speakeasy ambiance, and so much more. The best part is all of the magic is done right in front of you, at your table! The performances happen right at your table, making it one of the most memorable things to do in Chicago.
18. Zipline at The Forge: Lemont Quarries
Price: $40–$120
Location: Lemont, IL
If you love excitement, ziplines, and adventure courses at The Forge are among the most thrilling things to do in Chicago (technically just outside the city). You can climb towers, paddle in the quarry, and bike through forest trails. It’s perfect for families, friends, and adrenaline seekers looking for active things to do in Chicago.
19. Take a Segway Tour Through Downtown
Price: $55–$80
Location: Millennium Park & Lakeshore Routes
A Segway tour is one of the most fun and effortless things to do in Chicago. You glide past museums, parks, sculptures, and the lakefront while learning about the city’s history. It’s perfect for first-time visitors who want to see a lot without getting tired.
20. Attend a Chicago Fire Soccer Game
Price: $25–$100
Location: Soldier Field
If you’re searching for energetic things to do in Chicago, a Chicago Fire soccer match delivers. The stadium atmosphere is lively with chants, drums, and fireworks. Before or after the game, you get beautiful views of Lake Michigan and the skyline.
21. Try an Escape Room Adventure
Price: $30–$45
Location: Multiple Neighborhoods
Escape rooms are one of the most immersive things to do in Chicago. You solve clues, uncover secrets, and complete missions within 60 minutes. From haunted mansions to spy puzzles, each room feels like a movie. It’s perfect for groups looking for exciting things to do in Chicago indoors.
22. Kayak on the Chicago River
Price: $25–$75
Location: Riverwalk & Goose Island
Kayaking is one of the most scenic outdoor things to do in Chicago. You paddle between skyscrapers, pass bridges, and enjoy calm waters with breathtaking views. Sunset tours and architecture kayaking sessions offer unique experiences. It’s a peaceful yet adventurous activity that gives you one of the best perspectives of Chicago.
Discover the Best Things to Do in Chicago
Chicago is a city filled with excitement, culture, flavor, and unforgettable views. With endless things to do in Chicago, you can explore neighborhoods, enjoy museums, try iconic foods, and enjoy thrilling adventures around every corner. Whether you’re walking the lakefront, tasting deep-dish pizza, paddling on the river, laughing at comedy shows, or exploring the city’s art and architecture, there’s always something new waiting for you. Use this guide to plan your trip and start exploring — and if you’re ready to book activities, shows, or tours, Click Here or Book Now to begin your Chicago adventure Click Here.
