The Definitive 2026 Chicago Event Calendar: 15 Must-See Festivals, Exhibits, And Marathons

Planning your trip to the Windy City in 2026? You’ve come to the right place. Chicago’s event calendar for the upcoming year is already packed with massive music festivals, groundbreaking museum exhibits, and the return of iconic neighborhood street fairs. From the first bites of Restaurant Week in January to the final runners crossing the finish line of the Marathon in October, 2026 is shaping up to be one of the city's most vibrant years yet, offering an unparalleled mix of culture, cuisine, and world-class entertainment.

To help you navigate the year, this guide provides the freshest, most current information available as of December 15, 2025, ensuring you have the essential dates for the biggest happenings. Get ready to book your flights and secure your tickets, because these are the essential Chicago events you cannot afford to miss.

The Year in Culture: Major Festivals, Art, and Theater

Chicago is a city of neighborhoods, and its cultural calendar reflects this diversity, offering everything from massive lakefront concerts to intimate, world-renowned art fairs. The 2026 season brings back several annual blockbusters and introduces new, limited-time cultural experiences.

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Winter & Spring Essentials: Food, Film, and First Looks

The year kicks off with a focus on Chicago’s celebrated culinary and performing arts scenes, offering a perfect antidote to the winter chill. These events are highly anticipated and provide a deep dive into the city’s indoor cultural offerings.

• Chicago Restaurant Week: (January 23 – February 8, 2026) The city's premier dining event sees hundreds of restaurants across dozens of neighborhoods offering special prix-fixe menus for lunch and dinner, making fine dining accessible.
• First Bites Bash: This is the official kickoff party for Restaurant Week, typically held in late January, providing a sneak peek of the menus from top chefs.
• Chicago Theatre Week: (February 5 – 15, 2026) Theater lovers can snag deeply discounted tickets to major productions and smaller, innovative shows across the city.
• Tomorrow Never Knows (TNK): Held in January, this festival is a staple for indie music fans, showcasing emerging artists across multiple iconic Chicago venues like Metro and Lincoln Hall.

Groundbreaking Museum Exhibits in 2026

The city's world-class museums have already announced several major, limited-run exhibits that promise to be huge draws for art and design enthusiasts. These are key for those seeking unique cultural experiences.

• Yoko Ono: Music of the Mind: This major retrospective at the Museum of Contemporary Art (MCA Chicago) runs through February 22, 2026, offering a comprehensive look at the artist's conceptual works and music.
• Edgar Calel: Corn Mountain of Life (Ixim Juyu K'aslem): Scheduled for May 2 – September 13, 2026, this exhibition at the Art Institute of Chicago is a must-see for contemporary art lovers, showcasing the work of the Mayan Kaqchikel artist.
• Theaster Gates: Unto Thee: Running until February 22, 2026, at the Smart Museum of Art, this is the first solo museum exhibition in Chicago for the internationally celebrated local artist, Theaster Gates.
• Tiffany Lamps: Beyond the Shade: Visitors to the Driehaus Museum can explore this stunning collection of Tiffany lamps and decorative arts, on display through March 15, 2026.

Summer Festival Season: Music, Art, and Pride

Summer in Chicago is synonymous with outdoor festivals. From the massive crowds of Grant Park to the charming streets of the Old Town Triangle, the city truly comes alive with music, art, and community celebrations. The 2026 summer lineup is already shaping up to be legendary.

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The Music Festival Heavyweights

Chicago is home to some of the world's most famous music festivals. While official lineups are released closer to the dates, the windows for these major events are set:

• Lollapalooza 2026: The four-day music behemoth is tentatively scheduled for Thursday, July 30, through Sunday, August 2, 2026, in Grant Park. This is the crown jewel of the summer and requires planning well in advance.
• Windy City Smokeout: (July 8–12, 2026) A perfect blend of country music, craft beer, and world-class barbecue, this festival is a massive weekend-long tailgate party.
• Sueños Festival & Summer Smash: These two major festivals—Sueños focusing on Latin music and Summer Smash on hip-hop—are expected to return in 2026, continuing to solidify Chicago’s status as a top music destination.
• Beyond Wonderland Chicago: This major electronic dance music (EDM) festival is set to return to Huntington Bank Pavilion at Northerly Island on June 6 and 7, 2026.

Iconic Neighborhood Street Fairs

For a true taste of Chicago culture, the neighborhood street festivals are essential. These events bring local artists, food vendors, and musicians to the historic streets.

• Old Town Art Fair: (June 13–14, 2026) Celebrating its 75th year, this historic fair in the charming Old Town Triangle Historic District showcases juried art from hundreds of artists.
• Wells Street Art Festival: (June 13–14, 2026) Located just blocks away from the Old Town fair, this event is a lively complement, featuring a mix of art, food, and live music.
• Northalsted Market Days: This massive August street festival in the Northalsted neighborhood (formerly Boystown) is one of the largest LGBTQ+ street festivals in the country, celebrating community with multiple stages of entertainment.
• Chicago Pride Parade: The 55th annual parade is expected to march through the historic Northalsted neighborhood in late June, attracting over a million spectators.
• Chosen Few Picnic: (July 11, 2026) A legendary event for house music enthusiasts, this picnic in Jackson Park is the nation's longest-running house music festival.

The Autumn Highlight: Sporting and Architectural Feats

As the leaves begin to change, the pace doesn't slow down. Fall in Chicago is defined by one of the world's most famous races and a celebration of the city’s groundbreaking design heritage.

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The Bank of America Chicago Marathon 2026

The 48th running of the Bank of America Chicago Marathon is one of the city's most globally recognized events. The date for 2026 is confirmed, making it a key date for runners and spectators alike.

• Date: Sunday, October 11, 2026.
• The Event: The Marathon is one of the six World Marathon Majors, drawing tens of thousands of runners from over 100 countries to race through 29 of Chicago's diverse neighborhoods.
• Registration: The application and lottery process typically begins in the fall of the preceding year (late 2025), so potential participants should monitor the official website for 2026 entry details.

Architecture and Design

Chicago is the birthplace of the skyscraper and a hub for modern architecture. The city celebrates this legacy with major events:

• Chicago Architecture Biennial: This event is a massive, multi-venue exhibition and program series that explores contemporary design and architecture, offering free public programs and installations. The Biennial is a recurring event that draws global attention to Chicago's design leadership.

Planning Your 2026 Chicago Trip

Whether you are a music fanatic, an art connoisseur, or a marathon runner, Chicago in 2026 offers a dynamic and diverse calendar of events. Given the popularity of major festivals like Lollapalooza and the Chicago Marathon, booking accommodation and travel well in advance is highly recommended to secure the best rates and availability. Monitoring the official websites for ticket sales and lineup announcements will ensure you don't miss out on these incredible experiences.