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.