The ultimate Chicago bucket list

There are so many ways you can do Chicago — and if you’re going for the first timeyou’ll want to hit up all the classics and must-see spots.

We’ve put together this definitive list of the essential Chicago things to do and seefrom the city’s most iconic attractions to award-winning and under-the-radar restaurants. To be fairyou won’t be able to complete the bucket list in just one visit — but it’s a pretty good excuse to plan another trip back.

Eat and drink the best of the city

Sample iconic Chicago dishes

• Eat classic Chicago pizza…and lots of it! Decide for yourself between classic Chicago sfrom cheesy deep dish to crisp tavern .
• Pile seven toppings (but no ketchup) on a Chicago- hot dog… ideally at a baseball game.
• Discover the strangely addictive caramel-and-cheese combination from the world-famous Garrett Popcorn Shops.
• There’s no wrong way to enjoy an Italian beef sandwichwhether you prefer hot or sweetwet or dipped.
• Sample cuisines from around the world in our international foodie neighborhoodsfrom dim sum in Chinatown to family-owned taquerias in Little Village.
• Tackle a prime cut at Chicago’s steakhousesfrom old-school classics to buzzy newcomers.
• Enjoy summer in a cone with the colorful Original Rainbow Conea one-of-a-kind Chicago creation.
• Check off your dining bucket list at our Michelin-star restaurants (like three-star Alineaone of the world’s best restaurants) and James Beard Award winners.
• Taste your way through Chicago’s most iconic bitesincluding locally born dishes like the jibarito sandwich.
• Find great deals at hundreds of must-try restaurants around the city during the annual Chicago Restaurant Week.

Enjoy Chicago barsbreweriesand beyond

• Experience Chicago’s robust craft beer scene at over 100 craft breweries.
• Get spirited at Chicago’s world-class distillerieswhere you can try small-batch spirits made with Midwest ingredients.
• Try some of the city’s best mixology at these top Chicago cocktail bars.

Check off the essential cultural experiences

Explore our must-see museums

• Marvel at millions of artifacts and specimens at natural history haventhe Field Museum. Don’t forget to say hi to SUEthe most complete T.rex ever discovered.
• Explore the Art Institute of Chicago to admire one of the largest collections of Impressionist art outside the Louvre and the stunning Modern art wing.
• Visit the DuSable Black History Museumthe nation’s first independent museum dedicated to the history and culture of African Americans.
• Stand in a tornadostep inside a real U-boator travel deep down in a coal mine at the interactive Griffin Museum of Science and Industry.
• Meet a whole world of aquatic creaturesfrom stingrays to sea ottersat the lakefront Shedd Aquarium.
• Learn about the wonders of the universe at Adler Planetariumthe first planetarium in the Western Hemisphere.
• Go deeper into the story of our cityfrom the Great Chicago Fire to the jazz ageat the Chicago History Museum.
• Visit the Chicago Architecture Center for fascinating exhibits on the birth of the skyscraperour changing skylineand more.

Feel the beat of Chicago’s music and nightlife

• Hear masters of Chicago- blues at the city’s best-known blues clubsincluding Buddy Guy’s Legends.
• Discover the next generation of comedy stars (in the city that invented improv) at our comedy clubs like the illustrious The Second City.
• Step into the Jazz Age at the historic Green Mill Jazz Club (a favorite of Al Capone) and explore other fabled jazz venues in Chicago.
• Dance all night to house musica dance music genre born in Chicago’s underground club scene.
• Thalia Hall is a Pilsen landmark and indie music haven that’s also home to some of the neighborhood’s hottest dining.
• Catch unforgettable shows across genres at top Chicago music venuesfrom neighborhood clubs to historic theatres.

Find your seats for Chicago theatre

• Get tickets for a show at Broadway in Chicagowhich brings world premieres and classic hits to the city’s bustling downtown theatre district.
• See a show at one of Chicago’s Tony Award-winning theatreslike the Court Theatre and the star-studded Steppenwolf Theatre.
• Watch modern takes on the classics at the renowned Chicago Shakespeare Theater.
• Discover up-and-coming talent and avant-garde productions at neighborhood theatreslike the innovative A Red Orchid Theatre founded by Michael Shannon.
• Grab discounted tickets to top shows all around the city during Chicago Theatre Week.

Be wowed by top sights and attractions

Admire top sights and attractions

• You can’t leave Chicago without heading to Millennium Park to take a selfie with the city’s most iconic piece of public art — Cloud Gateaka “The Bean.”
• Hover just outside one of the world’s tallest buildings at The Ledgean all-glass balcony at Willis Tower’s Skydeck Chicago.
• Enjoy panoramic views and a heart-pounding thrill ride at 360 CHICAGO observation deck on Michigan Avenue.
• Stop at the Chicago Cultural Center to see the world’s largest Tiffany glass dome and enjoy a host of free events and exhibits.
• The Magnificent Mileone of the world’s most iconic shopping districtsis located in the heart of downtown along Michigan Avenue.
• Visit Frank Lloyd Wright’s Robie Housea UNESCO World Heritage site that exemplifies Wright’s signature Prairie .
• Admire famous architectural gems (like the Tribune TowerWrigley BuildingMarina Cityand more) in the city that invented the skyscraper.
• Step back in time at the Pullman National Historical Parkthe country’s first planned model industrial community.
• Discover under-the-radar attractions and hidden gems in our diverse neighborhoods.

Embark on waterfront adventures

• Ride a soaring Ferris wheelsample classic Chicago eatshop on a boat tourand more at lakefront Navy Pierone of the Midwest’s most popular attractions.
• Gaze up at the city skyline from a one-of-a-kind angle during a kayak tour of the Chicago River or lakefront.
• Stroll the buzzing Chicago Riverwalkhome to bustling outdoor cafeswine barsand shops.
• Learn the story behind Chicago’s most iconic architectural feats on an architecture boat cruiselike the Chicago Architecture Center River Cruise.
• See the skyline on the Chicago Water Taxithe most scenic way to get around town.

Adventure in the great outdoors

Feel the thrill of urban adventures

• Walk or bike on the 18-mile Lakefront Trailfeaturing jaw-dropping skyline viewssandy beachesand beachfront bars.
• Let the kids run and play at Maggie Daley Parkwhere you’ll find a climbing wallskating ribbonmini golfand more.
• Bikeskatewalkor run along The 606an elevated urban trail that cuts through some of the city’s hippest neighborhoods.
• Explore lakefront Grant Parkhome to top city events and the historic Buckingham Fountain.
• Go for a swimplay beach volleyballor relax in the sand at Chicago’s sun-soaked beaches.

City in a garden

• Find a moment of zen at the Lurie Gardena lush oasis in the heart of downtown.
• Stroll the meandering boardwalks and manicured gardens of Lincoln Park.
• Visit an authentic Japanese garden tucked away inside Jackson Park.
• Discover the secluded Alfred Caldwell Lily Poolhidden just north of Lincoln Park Zoo.
• Enjoy “landscape art under glass” at the historic Garfield Park Conservatoryone of the largest conservatories in the country.
• Wander past lagoonswillowsand a historic boathouse in Humboldt Park.

Attend iconic events

Catch top music festivals

• See music’s biggest names alongside up-and-coming local acts at Lollapaloozaone of the world’s most iconic festivals.
• Riot Fest features carnival rideslocal food vendorsand all things punk rock.
• Fuel up with beer and barbecue while listening to top country music artists at Windy City Smokeout.
• Experience the sounds of Chicago- blues from legendary artists at the Chicago Blues Festival.
• Feel the power of traditional choirs and contemporary groups at the Chicago Gospel Music Festival.
• Sueños Music FestivalChicago’s first-ever reggaeton festbrings an impressive lineup of Latin hitmakers to Grant Park.
• Hear living legends play at the lakefront Chicago Jazz Festivalcelebrating the city’s vibrant jazz history.
• The multi-venue World Music Festival brings artists and genres from around the world to Chicago.
• Chicago House Music Festival and Chosen Few Picnic celebrate house music in the city where it was born.
• Pack a picnic and hear live music under the stars at the Millennium Park Summer Music Series.

Cheer on Chicago sports

• Catch the beloved Chicago Cubs play a home game at historic Wrigley Fieldthe country’s second-oldest ballpark.
• Root for the Chicago White Sox at Rate Field; come early to tailgate and stay for post-game fireworks.
• Feel the electric energy at a Chicago Sky basketball game at Wintrust Arena.
• Watch the Chicago Bears take on opposing teams at lakefront Soldier Field.
• See the Chicago Blackhawks take the ice for fast-paced matches at the United Center.
• Also at the United Centercheer on the legendary Chicago Bulls as they bring the energy for every game.
• Enjoy the non-stop fun of a Chicago Fire soccer match at Soldier Field.

Mark your calendar for more can’t-miss events

• Attend the Chicago Auto Showthe largest auto show in North America.
• The city’s green river dyeing and St. Patrick’s Day celebrations are a true bucket-list item.
• The annual 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 neighborhoodattracting more than one million revelers each year.
• The free Chicago Air and Water Show on the city’s lakefront is the largest show of its kind in the country.
• Taste of Chicago offers a diverse range of the city’s award-winning cuisine and free concerts from top artists in Grant Park.
• Cheer on runners from all over the world at the Chicago Marathonone of the seven World Marathon Majors.
• Christkindlmarket Chicago is a magical holiday market in the heart of downtownd after traditional German Christmas bazaars.
• Kick off the holidays at The Magnificent Mile Lights Festivala nighttime parade that lights up the iconic street.
• ZooLights at Lincoln Park Zoo is an over-the-top holiday display that covers the historic zoo in millions of twinkling lights.

See the best attractions in Chicago at up to 50% savings with CityPASS.

Explore the famous Shedd Aquariumsee scientific discoveries at the Field Museumtake in spectacular views from the Skydeck and more! With two options to choose from and up to 9 days to enjoyyou can't go wrong.

Learn more