Discover 10 events, festivals, and experiences happening across Chicago this November, from live entertainment and seasonal attractions to can't-miss local events.

Christkindlmarket returns November 20 through December 24 at Daley Plaza and RiverEdge Park, with its Wrigleyville location running through December 31. The beloved German-inspired Christmas market features local vendors, holiday gifts, handcrafted ornaments, traditional German food, seasonal drinks, festive entertainment, and more. Admission is free.

Lightscape returns to the Chicago Botanic Garden November 13, 2026, through January 3, 2027, featuring a 1.3-mile illuminated trail filled with spectacular light installations, festive music, interactive displays, seasonal food and drinks, and plenty of photo opportunities. A must-see holiday experience for the season. Get tickets here.

Winterland at Gallagher Way returns November 20 through December 31, 2026, transforming the area outside Wrigley Field into a festive holiday destination. Visitors can enjoy outdoor ice skating, holiday train rides, Christkindlmarket Wrigleyville, Santa’s Workshop, holiday movies, seasonal entertainment, and more. Admission is free, with select activities available for an additional cost.

ZooLights returns to Lincoln Park Zoo November 20, 2026, through January 3, 2027, transforming the zoo into a holiday wonderland with more than 3 million lights, illuminated displays, a light tunnel, Ferris wheel rides, festive food and drinks, Santa visits, and seasonal entertainment. A Chicago holiday tradition for all ages, with select Mondays offering free admission. Get tickets here.

Wintrust Winter WonderFest returns to Navy Pier November 27, 2026, through January 3, 2027, transforming Festival Hall into a massive indoor holiday playground. Visitors can enjoy thrilling rides, ice skating, festive decorations, seasonal attractions, holiday entertainment, and family-friendly activities. General admission starts at $27, with ice skating included with every ticket. Get tickets here.

The 92nd Annual Chicago Thanksgiving Parade returns to State Street on Thursday, November 26, 2026, bringing a morning of giant balloons, elaborate floats, marching bands, live performances, and festive entertainment to downtown Chicago. The parade steps off at 7:40 AM at Ida B. Wells Drive and State Street, traveling north to Randolph Street. Admission is free, with VIP viewing available for purchase.

The 312 Comedy Festival returns to Chicago November 5–15, 2026, bringing 11 days of stand-up comedy, live shows, and special performances to venues across the city. This year's lineup features some of comedy's biggest names, including Nikki Glaser, Bert Kreischer, Michelle Wolf, Ali Siddiq, Joey Diaz, Ron White, and more. Performances will take place at The Chicago Theatre, Zanies, Park West, The Vic Theatre, Riviera Theatre, and Wintrust Arena. Get tickets here.

The Maggie Daley Park Ice Skating Ribbon returns November 13, 2026, through March 7, 2027, offering a unique outdoor skating experience through a quarter-mile winding ice path with stunning views of the Chicago skyline. Visitors can enjoy skate rentals, seasonal sessions, and one of downtown Chicago’s most popular winter activities.

The Winter Flower Show: Oh Deer! returns to Garfield Park Conservatory November 25, 2026, through January 3, 2027, featuring a festive indoor display of colorful poinsettias, lush greenery, seasonal plants, and illuminated Christmas trees. A perfect way to escape the cold and enjoy a little holiday magic in one of Chicago’s most beautiful conservatories. The exhibit is included with general admission. Get tickets here.

Jack Frost Holiday Pop-Up returns to Fulton Market at 170 N. Green Street for the 2026 holiday season, running November 28, 2026, through January 3, 2027. Visitors can enjoy outdoor ice skating, winter bumper cars, curling, axe throwing, holiday pop-up shops, festive cocktails, and more than one million holiday lights. Get tickets here.