November in Chicago is one of the most dynamic months of the year for locals and visitors alike. With the crisp air settling in and the city transitioning into the holiday season, you’ll find a mix of large-scale festivals, new restaurant openings and immersive cultural experiences. If you’re looking to explore the city’s energy, November events in Chicago offer something for every taste.
As October winds down, Chicago shifts gears. The leaves are still falling and many outdoor options remain, but many venues also begin their indoor programming for the colder months. According to Time Out Chicago’s November calendar, 2025 features a wide variety of events from food pop-ups to the first holiday markets. Time Out Worldwide Because the holiday rush has not yet peaked, November is a sweet spot for experiencing the city before it becomes ultra-busy.
Culinary & dining highlights: One standout for 2025 is the opening of Hooligan, a new 50-seat seafood & wine bar by Michelin-recognised chef Christian Hunter in the Time Out Market Chicago in November. Eater Chicago This makes late November a perfect time to combine an event outing with a special dinner.
Arts, music and culture: November brings top-tier concert and theatre events. For example, legendary artist Patti Smith and her band will perform their 50-year anniversary album at The Chicago Theatre on Nov 17 & 18. Madison Square Garden The city’s festival guide also lists numerous theatre shows, exhibits and family-friendly events this month. Choose Chicago+1
Family-friendly and outdoor options: Even in November you can still enjoy outdoor fun. The city’s event listings show tours, riverwalk activities and the frozen skating ribbon at Maggie Daley Park as part of the late-fall mix. Chicago on the Cheap Another popular event is the annual rugby match between Ireland national rugby union team and New Zealand national rugby union team at Soldier Field on Nov 1, 2025 — a major international sporting event this November in Chicago. The Sun
Buying tickets and planning ahead: Since November is less crowded than December but still popular, book early for big shows and dining openings. For theatre and concerts use major ticket sites such as Ticketmaster to secure seats. Ticketmaster
Neighborhoods to base your outing:
Smaller events worth watching include pop-up dining experiences, beer gardens, and local art markets. The “Jack’s Pumpkin Pop-Up” near Goose Island is running into early November with thousands of pumpkins and carnival games. Time Out Worldwide Looking ahead, early December events like the Christkindlmarket and ZooLights are already announced, so this month lets you gear up for the holiday fun.
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