Five Things To Do in Chicago: Nov. 7–9, 2025

From orchard visits to neighborhood fests, fall is full of reasons to get outside and soak it all in. We've rounded up a few local happenings to add to your list this weekend.

Step into the holidays at LEGO® Holiday Lane.

Kick off the season inside a life-size brick-built winter scene at LEGO® Holiday Lane, a three-day pop-up that blends festive nostalgia with hands-on play. Stroll a miniature "Main Street" lined with themed storefronts, design custom Minifigures, peek into a LEGO cinema, and browse sets inspired by movies, pets, gaming, and more. Kids can build a take-home ornament, hop aboard the DUPLO® Express, or add a heart to the community tree as part of the #BuildtoGive initiative, which donates LEGO sets to children in need.

Date: Nov. 7–9
Time: Fri 2–8 p.m.; Sat 11 a.m.–7 p.m.; Sun 12–6 p.m.
Cost: Free
Location: Water Tower Place, 835 Michigan Ave.
More Info: patch.com

  
Sip and sample at the Festival of Wood + Barrel-Aged Beer.

A cornerstone of the craft beer calendar, the Festival of Wood & Barrel-Aged Beer gathers top breweries from across the country for a weekend devoted to meticulously aged pours. Expect complex stouts, inventive sours, and a few experimental blends, each shaped by time spent in barrels that once held bourbon, wine, or spirits. Beyond sampling, the festival doubles as a major competition — brewers vie for medals and bragging rights that can change a beer's standing overnight. For enthusiasts interested in craftsmanship, flavor, and the art-meets-science side of brewing, it's one of the most anticipated tastings of the year..

Date: Nov. 7–8
Time: Fri 6–10 p.m.; Sat 1–5 p.m.
Cost: $97
Location: Credit Union 1 Arena, 525 S. Racine Ave.
More Info: fobab.com

Catch the Chicago Reel Shorts Film Fest.

This long-running festival returns with a lineup of bite-size cinema from around the world—comedies, dramas, horrors, and a few wonderfully off-kilter surprises. The Chicago International REEL Shorts Film Festival champions emerging filmmakers by keeping the atmosphere approachable and the ticket prices modest, making it an easy entry point for everyone. Expect a mix of polished gems and bold experiments, all best enjoyed with a crowd. If you like your movies smart, strange, or fast-moving, this showcase of global storytelling in under 20 minutes per film is a welcome weekend fix.

Date: Nov. 7–8
Time: Various Times
Cost: $15
Location: Chicago Filmmakers Theater, 1326 W. Hollywood Ave.
More Info: projectchicago.com 

Laugh out loud at 312 Comedy Festival.

Enjoy the was few days of The 312 Comedy Festival with a packed schedule of stand-up across Chicago, featuring household names, rising comics, and a range of shows sized from intimate club sets to marquee theater nights. With performances spread throughout the city, the festival makes it easy to catch an act that fits your comedy taste.

Date: Nov. 7–9
Time: Various Times
Cost: Various Pricing
Location: Various Locations
More Info: 312comedyfestival.com 

Explore The Instituto Gráfico de Chicago Print Fair.

The Instituto Gráfico de Chicago Print Fair offers a closer look at the city's printmaking community through demonstrations, hands-on activities, and work from local artists. Founded in 2010, the collective centers Latinx and Latin American printmaking traditions, creating space for both education and artistic exchange. Visitors can watch printmaking in action, try their hand at creating a piece, and browse prints available for purchase.

Date: Nov. 8
Time: 12–5 p.m.
Cost: Free
Location: Intuit Art Museum, 756 Milwaukee Ave.
More Info: art.org