There’s a lot of ways you can do Chicago. If you’re going for the first time, you’ll want to hit up all the classics. We’ve put together this definitive list of the essential Chicago musts, from iconic attractions to award-winning restaurants. To be fair, you won’t be able to complete the bucket list in a single weekend — but it’s a pretty good excuse to plan another trip back.
- Eat and drink the best of the city
- Check off the culture musts
- Be wowed by city sights
- Soak in the great outdoors
- Attend iconic events
Eat and drink the best of the city
Top Chicago eats
- Eat Chicago pizza…and lots of it! Decide for yourself between classic Chicago styles, from deep dish to tavern style.
- Pile seven toppings (but no ketchup) on a Chicago-style hot dog… it’s the only way.
- Devour handfuls of the caramel-and-cheese mix from the world-famous Garrett Popcorn Shop.
- Learn the lingo before you order an Italian beef sandwich.
- Taste the world in our global foodie neighborhoods, from dim sum in Chinatown to some of the city’s best tacos in Little Village.
- Tackle a prime cut at Chicago’s steakhouses — both legendary and new.
- Embark on an epicurean adventure at our Michelin-star restaurants (like three-star Alina) and James Beard Award winners.
- Savor summer with a colorful scoop — Chicago’s own Original Rainbow Cone.
- Eat your way through Chicago’s most iconic bites, including locally created dishes like the jibarito.
- Find great deals on must-try eats during the annual Chicago Restaurant Week.
Chicago bars, breweries, and beyond
- Experience the craft beer capital of the country with over 70 local craft breweries.
- Get spirited at Chicago’s world-class distilleries, from KOVAL to Chicago Distilling Company
- Try some of the city’s best mixology at these top Chicago cocktail bars.
Check off the culture musts
Experience Chicago’s music and nightlife
- Hear masters of Chicago-style blues at the city’s famous blues venues, including Buddy Guy’s Legends.
- Discover the next generation of comedy stars at iconic improv club The Second City.
- Relive the Jazz Age at the historic Green Mill Jazz Club in Uptown (it first opened in 1907 and was a favorite of Al Capone) and explore other one-of-a-kind jazz venues in Chicago.
- Dance all night to house music, a genre born in Chicago.
- See unforgettable shows at these top Chicago music venues, from neighborhood clubs to soaring theatres.
Explore our must-see museums
- Gaze up at a Titanosaur, the largest creature known to man, at the Field Museum. Don’t forget to say hi to SUE, the most complete and best-preserved T.rex ever discovered.
- Explore the Art Institute of Chicago to see one of the largest collections of Impressionist art outside the Louvre.
- Visit the DuSable Black History Museum, the nation’s first independent museum dedicated to the history and culture of African Americans.
- Stand in a tornado, inside a U-boat, or deep down in a coal mine at the interactive Griffin Museum of Science and Industry.
- Watch rare and local aquatic creatures in stunning habitats at the Shedd Aquarium.
- Marvel at the wonders of the universe at Adler Planetarium, the first planetarium in the Western Hemisphere.
- See remnants of the Great Chicago Fire and hop on the first ‘L’ car at the Chicago History Museum.
Find your seats for Chicago theatre
- Get tickets for a show at Broadway in Chicago, bringing world premieres and touring hits to the city’s downtown theatre district.
- See theatre stars and acclaimed shows at Chicago’s Tony Award-winning theatres.
- Catch modern takes on the classics at the renowned Chicago Shakespeare Theater.
- Discover up-and-coming talent at these cutting-edge neighborhood theatres.
- Grab discounted tickets to top shows during Chicago Theatre Week.
Be wowed by city sights
Top sights and attractions
- Stand outside one of the world’s tallest buildings at The Ledge, an all-glass balcony at Willis Tower’s Skydeck Chicago.
- TILT over the city and enjoy panoramic views at 360 CHICAGO observation deck at the former John Hancock Center.
- Head to Millennium Park to take a selfie with the city’s most iconic piece of public art — Cloud Gate, aka “The Bean”.
- Head to the Chicago Cultural Center for free public events and to see the world’s largest Tiffany glass dome.
- Visit the Robie House, a UNESCO World Heritage site designed by Frank Lloyd Wright.
- Admire architectural gems (like the Tribune Tower, Marina City, and more) in the city that invented the skyscraper.
- Step back in time at the historic Pullman National Monument.
- Discover under-the-radar attractions and hidden gems in our diverse neighborhoods.
Waterfront adventures
- Catch summer fireworks, take a Ferris wheel ride, and so much more at lakefront Navy Pier.
- Paddle through an architectural canyon on a kayak tour of the Chicago River or lakefront.
- Grab a drink on the award-winning Chicago Riverwalk, home to bustling alfresco restaurants and bars.
- Gaze up at Chicago’s most iconic architecture on an architecture boat cruise, like the Chicago Architecture Foundation Center River Cruise.
- See the skyline on the Chicago Water Taxi, the most scenic way to get around town.
Soak in the great outdoors
Urban adventures
- Go for a waterfront stroll through sandy beaches and green space on the 18-mile Lakefront Trail.
- Go ice skating or scale a climbing wall at Maggie Daley Park.
- Bike, skate, walk, run, and take in a little artsy culture along The 606.
- Explore beautiful Grant Park, home of top city events and the historic Buckingham Fountain.
- Catch a tan or a quick volleyball game at one of Chicago’s lakefront beaches.
City in a garden
- Lose yourself in zen of the Lurie Gardens with views of the city skyline.
- Stroll the nature boardwalk around the stunning South Pond in Lincoln Park Zoo.
- Visit an authentic Japanese garden hidden away inside Jackson Park.
- Find Lincoln Park’s secret garden, the secluded Alfred Caldwell Lily Pool.
- Take in “landscape art under glass” at Garfield Park Conservatory, one of the largest conservatories in the country.
Attend iconic events
Music festivals
- Pack a picnic and catch live music at Millennium Park free summer music series.
- Hang out with music fans — about 100,000 of them — at Lollapalooza in lakefront Grant Park.
- Riot Fest features carnival rides, local food vendors, and punk rock’s biggest names.
- Fuel up with barbecue from the nation’s premier pitmasters, while listening to top country music artists Windy City Smokeout.
- Experience the sounds of Chicago-style blues at the Chicago Blues Festival.
- Pitchfork Music Festival brings a curated line-up and laidback vibes to Union Park.
- Hear traditional choirs and contemporary urban gospel music at the Chicago Gospel Music Festival.
- Sueños Music Festival, Chicago’s first-ever reggaeton fest, brings an impressive lineup of Latin hitmakers
- Hear living legends play at the lakefront Chicago Jazz Festival.
- The multi-venue World Music Festival brings performers from around the world to Chicago.
- Chicago House Music Festival celebrates house music in the city where it was born.
Chicago sports
- See the Chicago Cubs play a home game at historic Wrigley Field, the country’s second-oldest ballpark.
- Root for the Chicago White Sox at Guaranteed Rate Field and stay for post-game fireworks.
- Feel the electric energy at a Chicago Sky basketball game at Wintrust Arena.
- Sing “Bear Down, Chicago Bears” during a Chicago Bears football game.
- Watch the Chicago Blackhawks take the ice at the United Center.
- Also at the United Center, cheer on the legendary Chicago Bulls basketball team.
- Enjoy the non-stop energy of a Chicago Fire soccer match at Soldier Field.
More can’t-miss events
- Celebrate the Lunar New Year in Chicago with traditional performances, colorful parades, culinary events, and more.
- Attend the Chicago Auto Show, the largest auto show in North America.
- The city’s green river dyeing is one of the most famous St. Patrick’s Day celebrations in the world.
- C2E2: Chicago Comic and Entertainment Expo is the largest pop culture convention in the Midwest.
- The joyous Chicago Pride Parade marches through the historic Northalsted neighborhood on the last Sunday of June.
- The lakefront Chicago Air and Water Show is the largest free show of its kind in the country.
- Taste of Chicago brings the city’s award-winning cuisine and free concerts from top artists to Grant Park.
- Cheer on runners from all over the world at the Chicago Marathon.
- Christkindlmarket Chicago is a magical holiday bazaar, styled after traditional German Christmas markets.
- ZooLights at Lincoln Park Zoo is an over-the-top light display with more than one million twinkling bulbs.
See the best attractions in Chicago at up to 48% savings with CityPASS.
Explore the famous Shedd Aquarium, see scientific discoveries at the Field Museum, take in spectacular views from the Skydeck and more! With two options to choose from and up to 9 days to enjoy, you can't go wrong.
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