Explore Chicago Year Round | Seasonal Fun | Choose Chicago

It’s always a great time to visit Chicago. Each season brings something new, from magical holiday markets in the winter to massive music festivals in the summer, cool architecture events in the fall to the Chicago River dyeing in the spring. Explore things to do and see in Chicago all year long.
Catch live music at a street fest, sip craft beer by the water, watch a movie under the stars, or dig your toes in the sand along our sun-soaked lakefront. Here’s a few things to do during summer in Chicago.
No one sings the blues quite like Chicago. Come celebrate over 35 years of performances by the world’s all-time greats and the city’s legacy as the birthplace of amplified blues.
The nation's only free, summer-long outdoor classical music series, featuring the acclaimed Grant Park Orchestra in parks throughout the city.
Grab a seat at the Jay Pritzker Pavilion for free weekly concerts under the stars all summer long
Pride is the biggest party of the year in Chicago. The annual fest is a massive LGBTQ+ celebration, followed by one of the largest Pride Parades in the country.
The best and brightest of the culinary industry gather in Chicago for these prestigious annual awards, along with a week of celebratory events.
Bust a move at this outdoor summer dance party, where instructors offer free lessons and live bands provide the beat.
This colorful celebration of Puerto Rican heritage takes over the cultural corridor in the Humboldt Park neighborhood.
Gospel music has deep roots in Chicago. Come celebrate the genre’s past and present with free shows from both traditional and contemporary performers.
The streets of the historic Chinatown neighborhood fill with food vendors, live music, cultural demonstrations, and more.
Experience the world’s largest free-admission food festival, where you can sample the best bites from dozens of local restaurants in lakefront Grant Park.
This laid-back festival celebrates house music, a genre created right here in Chicago, with live DJ performances in beautiful Jackson Park.
This annual outdoor fest brings country superstars to Chicago, along with some of the nation’s best beer and barbecue.
Celebrate black culture during the nation’s largest African American parade in historic Bronzeville and Washington Park.
This joyous event celebrates the Chicago-born genre by turning Millennium Park into an open-air dance floor.
Turn your eyes to the sky at the nation’s oldest and largest free-admission air and water exhibition, held at North Avenue Beach.
One of the country’s biggest music fests takes over Grant Park for four days with a star-studded lineup that includes 100+ bands across multiple stages.
Northalsted, Chicago’s LGBTQ+ mecca, hosts the largest street festival in the Midwest, with a weekend lineup of live music, drag queens, food and drink, DJs, and dancing.
In Chicago, autumn brings gourmet food fests, major art fairs, spooky parades, and groundbreaking architecture exhibits that keep the city buzzing all season long.
Hear jazz greats from Chicago and around the world during Chicago’s original free music festival in scenic Millennium Park.
Hear musical acts from around the world at the annual World Music Festival, the largest and longest-running international music festival in the country.
Mingle with celebrity chefs and try some of Chicago’s best bites at this fine-dining food festival put on by Bon Appétit.
This free, multi-venue fest celebrates the finest in local jazz, plus appearances by national and international acts.
This three-day fest is known as a music mecca for all things, alternative, punk, hip-hop, and rock, known for its reunions and full-album performances.
Take a ride down iconic Lake Shore Drive during this annual biking event. Pedal down 30 miles of scenic lakefront, completely car free.
This is the second longest-running film festival of its kind, bringing audiences 10 days of the LGBTQ+ films from around the world.
Get ready to race or cheer from the crowd. One of the six World Marathon Majors, the Chicago Marathon takes runners through 29 neighborhoods.
Get behind-the-scenes access to over 250 Chicago buildings, including many that aren’t typically open to the public, during this free, city-wide architecture fest.
Tour private homes in the historic Pullman neighborhood, including many century-old landmark buildings.
This surreal evening parade celebrates Halloween with a procession of fantastical floats, puppets, and performances by local artists from every field.
A can’t-miss for film buffs, this is the longest-running international film festival in America, with 12 days of film screenings and events.
Experience an authentic Día de los Muertos with this free celebration at the National Museum of Mexican Art, featuring live music, face painting, art activities, traditional foods, and more.
This annual parade is a classic Chicago tradition, featuring marching bands, equestrian acts, ballerinas, and giant helium balloons, all along Chicago’s State Street.
Catch this century-old Chicago tradition, marking the beginning of the holiday season with the lighting of the city’s official Christmas Tree.
This annual parade illuminates more than one million twinkling lights along one of Chicago’s most iconic streets.
Hit the ice for free beneath Cloud Gate, aka “The Bean”, at Millennium Park or wind around the Skating Ribbon at neighboring Maggie Daley Park.
Wander a charming German holiday market in Daley Plaza, where you can find mulled wine, baked goods, hand-blown ornaments, artisan woodwork, and more.
Chicagoans never let a little cold cramp our style. When the temperature dips, the city stays warm with magical parades, holiday markets, culinary celebrations, and more. Check out things to see and do during winter in Chicago.
Each winter, Chicago’s free zoo is transformed with over 2.5 million twinkling lights, plus live ice-sculpting, photo ops with Santa, hot chocolate, and more.