The Best Times to Visit Chicago
When to Visit Chicago and What to Do?
If you’re wondering about the best time to visit Chicago, then read on. From the blooming beauty of spring to the festive cheer of Christmas, each season in The Windy City brings its own charm and attractions.
Relish mouth-watering food and drink at autumnal festivals, or immerse yourself in the city’s energetic music events during summer. Whether you’re drawn to the city’s iconic shopping streets or captivated by its architecture, Chicago promises a memorable adventure at any time of the year.
1. Spring (March to May)
An ideal time for both nature lovers and sports enthusiasts
Good for: Families, Couples, Photo
Spring in Chicago is a beautiful season to experience the city’s transformation. As the winter chill fades, the parks and gardens of Chicago burst with life, showcasing a stunning array of tulips, daffodils, and cherry blossoms. This season also marks the beginning of baseball, with the Chicago Cubs and White Sox games bringing excitement and tradition to iconic fields.
Rooftop bars, al fresco patios, and waterfront terraces reopen, so you can enjoy Chicago’s tasty food scene with a side of beautiful views. Don’t miss Art on the Mart, which projects incredible digital art onto the Merchandise Mart building.
Spring (March to May)
2. Fall (September to November)
A city bursting with color
Good for: Families, Couples, Budget
As fall arrives and trees transform into a tapestry of reds, oranges, and golds, Chicago’s parks and neighborhoods become a mesmerizing sight. The mild temperatures ensure exploring is comfortable and fun, and it’s a fantastic season for sports fans to catch a Chicago Bears game or support the Bulls and Blackhawks.
Watch the world go by at a cozy cafe with a pumpkin spice latte and a plate of butternut squash ravioli, or opt for an architecture cruise to marvel at picturesque views of iconic buildings framed by autumn foliage. Visit the Chicago Botanic Garden to fully immerse yourself in the vibrant fall colors away from the city’s hustle and bustle.
Fall (September to November)
3. Halloween (October 31st)
Spooky celebrations and thrills abound
Good for: Families, Nightlife, Photo
Visiting Chicago during Halloween is a must for both families and those who love a good scare. The renowned Arts in the Dark Parade on State Street celebrates the holiday with illuminated floats, giant puppets, and performances that kids adore. Alternatively, Chicago’s haunted attractions, like the 13th Floor Haunted House near Rosemont, promise spine-tingling thrills.
Jack’s Pumpkin Pop-Up on Goose Island is another stand-out thanks to its massive corn maze and carnival games. For something unique, explore the Night of 1,000 Jack-o’-Lanterns at the Chicago Botanic Garden, where intricately carved pumpkins showcase incredible artistry. Don’t miss the city’s bars and restaurants, either, as they transform into spooky playgrounds with themed cocktails and decor.
Halloween (October 31st)
4. St. Patrick’s Day Weekend
A longstanding celebration filled with tradition
Good for: Families, Couples, Photo
Celebrate Irish culture by spending St. Patrick’s Day in Chicago. The highlight is the dyeing of the Chicago River, turning it a brilliant emerald green with an eco-friendly formula. Thousands of spectators flock to the streets to see this visual spectacle, along with parades reflecting different neighborhoods’ personalities and heritage.
Explore legendary Irish pubs offering live music and whiskey tastings, marvel at green-lit skyscrapers, and sample special menus at top restaurants. For a unique experience, join a St. Patrick’s Day-themed boat cruise on the Chicago River, where Irish music, drinks, and dancing celebrate the city’s love for the Irish.
St. Patrick’s Day Weekend
5. Food and Drink Festivals (September and October)
A smorgasbord of culinary offerings
Good for: Couples, Food, Nightlife
Chicago’s food and drink festivals during September and October are a culinary paradise. Expect a showcase of global flavors, from Greek souvlaki to Korean BBQ, from award-winning food trucks and restaurants across the city. Chef-driven experiences include live cooking demos and tasting pavilions featuring renowned talent, making them a gourmet’s dream. Many festivals support local causes, too, promoting sustainable farming and food education.
Visit Lincoln Square’s Apple Fest for a delightful blend of autumn flavors and community spirit, or attend the Taste of Chicago, one of America’s largest outdoor food events. There are dozens of festivals to check out, many of which also feature live bands, DJs, and art installations, so look online before you go.
Food and Drink Festivals (September and October)
6. Summer (June to August)
For beach days and skyline views
Good for: Adventure, Food, Photo
With over 26 miles of lakefront, a summer in Chicago is all about soaking up the sun. Dine along the iconic Chicago Riverwalk or explore the rooftop scene for drinks and cocktails with breathtaking views. Alternatively, grab takeout from a nearby eatery and enjoy Chicago’s expansive green spaces or beaches. We particularly love the laidback Montrose Beach for its kayak rentals and volleyball.
Cinema under the stars is a beloved tradition, with outdoor movies transforming parks and plazas into open-air cinemas. Visit during the Windy City Smokeout that brings together award-winning BBQ joints from across the USA, offering mouthwatering delights to accompany those balmy summer nights.
Summer (June to August)
7. Music Festivals (June, July, August)
Renowned hub for music of all genres
Good for: Couples, Families, Nightlife
Chicago’s summer music festivals are a must for any music lover. With genres spanning jazz, blues, hip-hop, and more, these festivals bring together talent both global and local. Iconic venues like Grant Park and Millennium Park provide stunning urban backdrops for world-class events like Lollapalooza and the World Music Festival.
Beyond music, festivals include art installations, food trucks, and interactive zones, creating a cultural celebration for the senses. Many festivals are even free to attend, like the famous Chicago Blues Festival or the Chicago Gospel Music Festival. Take in the sense of community and inclusivity and celebrate music as a unifying force.
Music Festivals (June, July, August)
8. Thanksgiving (November)
A heartfelt parade bringing in the holiday spirit
Good for: Families, Photo, Food
Thanksgiving in Chicago is a time of tradition and community. The historic Chicago Thanksgiving Parade, first held in 1934, is a beloved event reflecting the city’s resilience and diversity. With giant balloons, colorful floats, and live performances, it’s a joy for all ages. The parade is free to attend, making it accessible to everyone.
After the parade, explore top attractions like Millennium Park and the Christkindlmarket, which opens on Thanksgiving weekend. Consider a visit to the Skydeck Chicago for breathtaking city views and a unique perspective on the city’s Thanksgiving festivities.
Thanksgiving (November)
9. Cultural Celebrations (June, July, August)
Melting pot of cultures
Good for: Families, Couples, Photo
Visiting Chicago when its cultural celebrations are in full swing is a wonderful way to immerse yourself in the city’s rich multi-heritage tapestry. You could celebrate community and education with music and dance at The Bud Billiken Parade, the nation’s largest African American parade. Meanwhile, the Chinatown Summer Fair offers lion dances and Asian cuisine, while the Puerto Rican Fest features live salsa and vibrant performances.
These events are deeply rooted in their neighborhoods and offer unforgettable photo ops and kids’ zones, educational booths, and local vendors create family-friendly experiences. Arrive early to find a good spot for parade viewing, and don’t forget your camera to capture the colorful costumes and lively atmosphere.
Cultural Celebrations (June, July, August)
10. Christmas
Festive traditions in the Windy City
Good for: Families, Photo, Nightlife
Christmas in Chicago is a magical experience and promises a truly unforgettable vacation. The Christkindlmarket, modeled after Germany’s historic markets, draws visitors from all over eager for handcrafted gifts and mulled wine. Dazzling light displays transform the city into a glowing wonderland, with events like the Magnificent Mile Lights Festival and the Botanic Garden’s Lightscape.
An enchanting evening surrounded by millions of lights and synchronized music makes for a lovely date or family activity. Try ice skating at Millennium Park or Maggie Daley Ice Ribbon for a quintessential winter experience with stunning skyline views.
Christmas
This article includes opinions of the Go Guides editorial team. Hotels.com compensates authors for their writing appearing on this site; such compensation may include travel and other costs.