The ultimate Chicago bucket list

There are so many ways you can do Chicago — and if you’re going for the first time, you’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 see, from the city’s most iconic attractions to award-winning and under-the-radar restaurants. To be fair, you 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 styles, from cheesy deep dish to crisp tavern style.
• Pile seven toppings (but no ketchup) on a Chicago-style 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 sandwich, whether you prefer hot or sweet, wet or dipped.
• Sample cuisines from around the world in our international foodie neighborhoods, from dim sum in Chinatown to family-owned taquerias in Little Village.
• Tackle a prime cut at Chicago’s steakhouses, from old-school classics to buzzy newcomers.
• Enjoy summer in a cone with the colorful Original Rainbow Cone, a one-of-a-kind Chicago creation.
• Check off your dining bucket list at our Michelin-star restaurants (like three-star Alinea, one of the world’s best restaurants) and James Beard Award winners.
• Taste your way through Chicago’s most iconic bites, including 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 bars, breweries, and beyond

• Experience Chicago’s robust craft beer scene at over 100 craft breweries.
• Get spirited at Chicago’s world-class distilleries, where 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 haven, the Field Museum. Don’t forget to say hi to SUE, the 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 Museum, the nation’s first independent museum dedicated to the history and culture of African Americans.
• Stand in a tornado, step inside a real U-boat, or travel deep down in a coal mine at the interactive Griffin Museum of Science and Industry.
• Meet a whole world of aquatic creatures, from stingrays to sea otters, at the lakefront Shedd Aquarium.
• Learn about the wonders of the universe at Adler Planetarium, the first planetarium in the Western Hemisphere.
• Go deeper into the story of our city, from the Great Chicago Fire to the jazz age, at the Chicago History Museum.
• Visit the Chicago Architecture Center for fascinating exhibits on the birth of the skyscraper, our changing skyline, and more.

Feel the beat of Chicago’s music and nightlife

• Hear masters of Chicago-style blues at the city’s best-known blues clubs, including 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 music, a 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 venues, from neighborhood clubs to historic theatres.

Find your seats for Chicago theatre

• Get tickets for a show at Broadway in Chicago, which 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 theatres, like 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 theatres, like 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 Gate, aka “The Bean.”
• Hover just outside one of the world’s tallest buildings at The Ledge, an 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 Mile, one of the world’s most iconic shopping districts, is located in the heart of downtown along Michigan Avenue.
• Visit Frank Lloyd Wright’s Robie House, a UNESCO World Heritage site that exemplifies Wright’s signature Prairie style.
• Admire famous architectural gems (like the Tribune Tower, Wrigley Building, Marina City, and more) in the city that invented the skyscraper.
• Step back in time at the Pullman National Historical Park, the 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 wheel, sample classic Chicago eats, hop on a boat tour, and more at lakefront Navy Pier, one 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 Riverwalk, home to bustling outdoor cafes, wine bars, and shops.
• Learn the story behind Chicago’s most iconic architectural feats on an architecture boat cruise, like the Chicago Architecture Center River Cruise.
• See the skyline on the Chicago Water Taxi, the 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 Trail, featuring jaw-dropping skyline views, sandy beaches, and beachfront bars.
• Let the kids run and play at Maggie Daley Park, where you’ll find a climbing wall, skating ribbon, mini golf, and more.
• Bike, skate, walk, or run along The 606, an elevated urban trail that cuts through some of the city’s hippest neighborhoods.
• Explore lakefront Grant Park, home to top city events and the historic Buckingham Fountain.
• Go for a swim, play beach volleyball, or relax in the sand at Chicago’s sun-soaked beaches.

City in a garden

• Find a moment of zen at the Lurie Garden, a 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 Pool, hidden just north of Lincoln Park Zoo.
• Enjoy “landscape art under glass” at the historic Garfield Park Conservatory, one of the largest conservatories in the country.
• Wander past lagoons, willows, and 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 Lollapalooza, one of the world’s most iconic festivals.
• Riot Fest features carnival rides, local food vendors, and 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-style 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 Festival, Chicago’s first-ever reggaeton fest, brings an impressive lineup of Latin hitmakers to Grant Park.
• Hear living legends play at the lakefront Chicago Jazz Festival, celebrating 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 Field, the 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 Center, cheer 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 Show, the 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 neighborhood, attracting 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 Marathon, one of the seven World Marathon Majors.
• Christkindlmarket Chicago is a magical holiday market in the heart of downtown, styled after traditional German Christmas bazaars.
• Kick off the holidays at The Magnificent Mile Lights Festival, a 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 49% 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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