From Lollapalooza to the Chicago Thanksgiving Parade: Illinois’s Biggest Annual Events by Month (2026 Guide)
Illinois, anchored by Chicago but rich far beyond it, hosts some of the Midwest’s most influential annual events. The state’s calendar blends world-class music festivals, deep-rooted civic traditions, sports spectacles, and cultural celebrations shaped by immigration, architecture, and urban life.
Below is a month-by-month guide to Illinois’s biggest annual events in 2026, with expanded coverage of the most distinctive and high-impact celebrations.
Read more: 2026 Illinois Public School Calendar: Key Dates, Breaks, and What Families Should Know
January: Chicago Restaurant Week & Winter Culture
January is defined by Chicago Restaurant Week, a citywide dining event that draws locals and visitors during the winter season. Museums, theaters, and cultural institutions also roll out winter programming, making it a strong month for indoor culture.
February: Chicago Auto Show
Chicago Auto Show
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Held at McCormick Place, the Chicago Auto Show is North America’s largest auto show and one of the most influential automotive events in the world.
Running for more than a century, the show attracts global manufacturers, media, and hundreds of thousands of attendees. Its scale and longevity make it one of Illinois’s most internationally recognized annual events.
March: St. Patrick’s Day & Cultural Traditions
Chicago St. Patrick’s Day
Each March, Chicago famously dyes the Chicago River green—a tradition known worldwide. Combined with parades and citywide celebrations, it’s one of the most visually iconic St. Patrick’s Day events anywhere in the U.S.
April: Spring Festivals & Arts Season
April marks the return of outdoor festivals, architecture tours, and neighborhood events as the city transitions into spring.
May: Chicago Blues Festival & Memorial Day Weekend
Chicago Blues Festival
As the birthplace of modern electric blues, Chicago celebrates its musical legacy with the largest free blues festival in the world, held annually at Millennium Park.
June: Pride Month & Summer Kickoff
Chicago Pride Parade
One of the largest Pride parades in the Midwest, Chicago Pride draws massive crowds and reflects the city’s long-standing LGBTQ+ activism and inclusivity.
July: Taste of Chicago & Independence Day
Taste of Chicago
Taste of Chicago is one of the largest food festivals in the world, showcasing the city’s diverse neighborhoods, iconic dishes, and culinary innovation. It’s a major summer draw for both locals and visitors.
August: Lollapalooza
Lollapalooza
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| Lollapalooza |
Lollapalooza is Illinois’s most globally recognized event. Held in Grant Park, it attracts top international artists and hundreds of thousands of fans each year.
More than a music festival, Lollapalooza positions Chicago as a global pop-culture capital during the summer, with international media coverage and major economic impact.
September: Chicago Jazz Festival & Fall Culture
Chicago Jazz Festival
Another major free music event, the Chicago Jazz Festival celebrates the city’s deep jazz roots with performances by renowned artists in Millennium Park.
October: Chicago Marathon & Fall Events
Bank of America Chicago Marathon
One of the World Marathon Majors, the Chicago Marathon attracts elite runners and participants from around the globe. Its flat, fast course and enthusiastic crowds make it one of the most popular marathons worldwide.
Read more: Illinois Calendar 2025: List of Festivals in Culture, Music, and Heritage
November: Chicago Thanksgiving Parade
Chicago Thanksgiving Parade
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| Chicago Thanksgiving Parade |
A beloved city tradition, this parade officially kicks off the holiday season with balloons, floats, and performances along State Street.
December: Christkindlmarket & Holiday Season
Christkindlmarket Chicago
Inspired by traditional German Christmas markets, Christkindlmarket is one of Chicago’s most popular winter attractions, drawing millions of visitors each holiday season.
Why Illinois’s Major Events Stand Out
Illinois’s biggest annual events reflect the state’s strengths: musical heritage, architectural beauty, cultural diversity, and large-scale civic traditions. From the global draw of Lollapalooza to century-old institutions like the Chicago Auto Show, these events shape how the world experiences Illinois.
