Chicago is a must-visit destination all year round — from our magical winters to our stunning summers, our crisp falls to our buzzing springs, there’s something unique to do and see in every season.
But if you can only plan one trip to our great city this year, what’s the best time to come?
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The answer is different for every traveler. Your perfect Chicago experience might mean beach days and music festivals or holiday markets and snowy streets. No matter what kind of trip you’re planning, there’s a Chicago season that’s right for you.
Here’s how to find the best time for you to visit Chicago:
Spring in Chicago
March through May
Chicago is bursting with life in the spring. You’ll find tulip-studded streets, city parks filled with cherry blossoms, lighter crowds, milder temperatures, the start of baseball season, and tons of art events and exciting cultural happenings.
Top spring activities in Chicago
- A classic Chicago experience, the city’s boat cruises set sail on the river and lake each spring.
- Hop in a kayak and paddle down the scenic Chicago River to soak in skyline views.
- Shop artisan markets that pop up all over the city, featuring local artists, artisans, and crafters.
- Bike the Lakefront Trail, an 18-mile stretch of paved path along the Lake Michigan shoreline.
- See the city burst into bloom with spring flowers, from our neighborhood parks to The Magnificent Mile.
- Catch the Chicago Cubs or White Sox play at one of Chicago’s iconic stadiums, including the second-oldest ballpark in the country.
Top spring events in Chicago
- St. Patrick’s Day: Chicago’s iconic green river dyeing is a true bucket list item.
- C2E2: The largest pop culture convention in the Midwest.
- Chicago Latino Film Festival: Highlighting Latino filmmakers for more than 40 years.
- EXPO Chicago Contemporary Art Fair: A top international art fair takes over Navy Pier.
- Sueños Music Festival: Featuring Latin music’s hottest stars in downtown Grant Park.
- Pullman Railroad Days: Step back in time at Chicago’s National Monument.
Explore more things to do and see during spring in Chicago.
Summer in Chicago
June through August
Summer in Chicago means beaches, festivals, and patio dining are all in full swing. This is the best time of year in Chicago for all things outdoors, from cocktails on a rooftop to swimming in Lake Michigan to strolling the scenic Chicago Riverwalk.
Top summer activities in Chicago
- Make time to explore the Chicago Riverwalk, home to waterfront restaurants and panoramic city views.
- Navy Pier is your family-friendly summer headquarters, with activities and events for all ages.
- Summer is outdoor dining season, when you can dine on a soaring rooftop bar or a charming sidewalk cafe.
- Take advantage of Chicago’s full calendar of free summer music festivals in downtown Millennium Park.
- Chicago’s scenic beaches are the perfect place to swim, relax in the sand, and take in skyline views.
Top summer events in Chicago
- Chicago Gospel Music Festival: Enjoy powerful voices and uplifting performances in Millennium Park.
- Chicago Blues Festival: A free festival honoring the legacy of Chicago’s signature blues scene.
- Chicago Pride Parade: This legendary celebration attracts more than a million spectators.
- NASCAR Chicago Street Race: Feel the thrill of NASCAR in the heart of downtown Chicago.
- Chicago Air and Water Show: The largest free air and water show in the country takes over the city’s scenic lakefront.
- Lollapalooza: This iconic music festival showcases today’s hottest names in music.
- Chicago House Music Festival: Hear free house music in the city where it was born.
- Chicago Jazz Festival: This free fest brings jazz legends to Millennium Park over Labor Day weekend.
Explore more things to do and see during summer in Chicago.
Fall in Chicago
September through November
Autumn in Chicago brings crisp temperatures, colorful foliage, world-renowned film festivals, and one-of-a-kind Halloween celebrations. Plus, don’t miss a packed calendar of cultural events celebrating history, art, architecture, and beyond.
Top fall activities in Chicago
- Bask in the season’s breathtaking foliage, with autumnal colors and golden hues emerging across the city.
- Autumn brings a slate of must-see art and architecture events, covering the past, present, and future of design.
- Get your thrills and chills on a ghost tour of Chicago, featuring the city’s more supernatural sites.
- Celebrate Halloween with only-in-Chicago traditions, from family-friendly pop-ups to nighttime parades.
- Fall is theatre season in Chicago, when a diverse group of hot new shows light up the city’s many stages.
- Get a taste of the city during top food festivals, covering international cuisine and iconic Chicago dishes.
Top fall events in Chicago
- Arts in the Dark: A whimsical evening parade that will enchant the whole family.
- Open House Chicago: Enjoy behind-the-scenes access to Chicago’s diverse architectural gems.
- Historic Pullman House Tours: Take a peek inside historic homes in this landmark neighborhood.
- Chicago Gourmet: This elevated food festival brings top chefs, high-end tastings, and exciting culinary events.
- Chicago International Film Festival: North America’s longest-running international competitive film festival.
- Hyde Park Jazz Festival: Jazz fans won’t want to miss this long-running music fest on the city’s historic South Side.
- Taste of Chicago: Take a bite of Chicago’s diverse dining scene during this sprawling outdoor food fest.
- The Magnificent Mile Lights Festival: Kick off the holidays at this magical evening parade and fireworks show.
Explore more things to do and see during fall in Chicago.
Winter in Chicago
December through February
Winter is a truly magical time in Chicago. The holiday season brings festive traditions, dazzling light displays, and bustling holiday markets. You’ll also discover dining deals, cheap theatre tickets, cultural happenings, fresh art exhibits, outdoor ice skating rinks, and so much more.
Top winter activities in Chicago
- Enjoy ice skating under a snowy skyline at outdoor rinks in city parks.
- Marvel at the holiday lights that illuminate the city’s parks, streets, zoos, and beyond.
- Sip a festive cocktail at one of the city’s decked-out winter rooftop bars.
- Warm up inside one of Chicago’s acclaimed museums, from intimate galleries to sprawling interactive spaces.
- Admire winter blooms at the Garfield Park Conservatory, home to an array of flora and fauna.
- Visit the polar animals at the historic Lincoln Park Zoo, free and open to the public all winter long.
- Experience the city’s live theatre and comedy scene (and even score discounted tickets) at venues across the city.
Top winter events in Chicago
- Christkindlmarket: Enjoy all the charm of a classic German Christmas market in downtown Chicago.
- ZooLights: This beloved winter tradition blankets the zoo in millions of twinkling lights.
- Chicago Restaurant Week: Enjoy special prix fixe menus at hundreds of local restaurants.
- Chicago Theatre Week: Find value-priced tickets to comedy and theatre shows across Chicago.
- Lunar New Year: Discover cultural celebrations and colorful parades welcoming the new year.
- Chicago Auto Show: First staged in 1901, this annual event is the largest auto show in North America.
- New Year’s Eve fireworks: Ring in the new year with a dazzling fireworks display on Chicago’s waterfront.
Explore more things to do and see during winter in Chicago.
