Five Things To Do in Chicago: Dec. 5–7, 2025

Winter weather has arrived! Layer up, follow the holiday lights, and catch a few can't-miss events this weekend.

Spend a day at Holiday Road.
Western Avenue turns into a full-blown holiday corridor for this all-day neighborhood takeover stretching from 99th to 115th streets. Pop into indie shops, grab a cookie tin for the hop-on-hop-off trolley route, and dip into everything from kids' crafts and photo ops to beer pairings and holiday cocktails. Dozens of local businesses get in on the action, with pop-ups, live music, scavenger hunts, and enough festive programming to keep you busy from breakfast pancakes to evening concerts. It's one of Beverly/Morgan Park's biggest annual showcases, and an easy excuse to spend the day supporting the neighborhood's small businesses.

Date: Dec. 6
Time: Various Times
Cost: Free
Location: Western Ave. from 99th St. to 115th St.
More Info: mpbhba.org

Follow the festive trail at Winter Wonderland & Tree Lighting.
Wicker Park/Bucktown launches its holiday season with a family-friendly afternoon that sprawls across the neighborhood's shopping corridors. Start with free Santa photos, s'mores by the fire, and a scavenger hunt that could land you a holiday shopping spree. Rickshaws and shuttles ferry visitors between stops like the North Pole and Whoville, while local boutiques roll out specials for early gift-getters. The day ends in classic neighborhood fashion: cocoa, carolers, and the annual tree lighting at the Damen Avenue fountain.

Date: Dec. 6
Time: 1–5 p.m.
Cost: Free
Location: 1260 N. Milwaukee Ave.
More Info: business.wickerparkbucktown.com

Shop local at the Digs Holiday Market.
The Digs opens its studio doors for an afternoon market showcasing small-batch ceramics, handmade goods, and work from local artists. Visitors can browse fresh pieces from studio members, discover new small businesses, and pick up one-of-a-kind gifts you won't find anywhere else. It's also a chance to preview next year's classes and workshops — ideal for anyone looking to expand their creative repertoire in 2026.

Date: Dec. 6
Time: 2–6 p.m.
Cost: Free
Location: The Digs Chicago, 333 N. Oakley Blvd.
More Info: instagram.com 

Get hip to Old Town's Holiday Hop.
Old Town's bar scene goes full holiday mode for this roving celebration along Wells Street, where more than ten spots dress up with over-the-top décor, themed drinks, and all the seasonal kitsch you'd expect. Expect DJs, photo ops, ugly-sweater battles, and the occasional Santa sighting as you make your way from stop to stop. If you're looking for a night out that embraces holiday chaos in the best way, this is the hop to hit.

Date: Dec. 6
Time: 12–7 p.m.
Cost: $15+
Location: Various Locations
More Info: gce.ticketsauce.com 

Paint your own holiday keepsake at Sleigh the Canvas.
The Sheraton's holiday takeover turns into a full sensory workshop during this festive sip-and-paint session inside the hotel's Sleigh Bar pop-up. Create a pair of hand-painted ornaments, sample three wine-and-bite pairings tailored for the event, and have your camera ready for a photo op with Santa himself.

Date: Dec. 6
Time: 4–6 p.m.
Cost: $24+
Location: Sheraton Grand Chicago Riverwalk, 301 E. North Water St.
More Info: sheratongrandchicago.com