Five Things To Do in Chicago: Nov. 28–30, 2025

Winter is easing in, and with it comes a new lineup of reasons to brave the cold. Here are a few standout events worth bundling up for this weekend.

Kick off the holiday season with Bronzeville's Takeover on Small Business Saturday.
Celebrate the 10th annual Small Business Saturday on King Drive in Bronzeville — a day designed to spotlight the neighborhood's local shops, creators, and community spirit. Over 20 small businesses and vendors, including vegan bakeries, candle makers, and artisan tea sellers, set up shop while live dancers, carolers, and a tree-lighting bring holiday energy. Grab free hot cocoa and enjoy appearances by celebrity guests and performances around the 35th & King corridor.

Date: Nov. 29
Time: 8 a.m.–5 p.m.
Cost: Free
Location: Absolutely Anything Essential, 3521 S. King Dr.
More Info: eventbrite.com

Find Holiday Gems at the Chicago Artisan Market.
The Chicago Artisan Market returns to Artifact Events in Ravenswood for a curated indoor holiday edition. More than 200 creators will display handmade goods, from home décor and jewelry to fashion and art, across two floors, with café seating, plated food, and a bar serving wine, beer, and cocktails. It's a festive way to shop small, with plenty of space to find unique gifts and connect with local makers. Bonus, kids under 12 get in free.

Date: Nov. 29–30
Time: 11 a.m.–5 p.m.
Cost: $8+
Location: Artifact Events, 4325 N. Ravenswood Ave.
More Info: chicagoartisanmarket.com

Support local at the SAUCED Small Business Saturday Market.
SAUCED brings together some of the most creative independent shops for a night market full of food, design, and spirit. Browse boutiques like The Painted Loom, Midwest Nice, and Wicked Woods & Goods while sipping cocktails made with Apologue spirits and enjoying bites from Pies of London. Live music from Shon Dervis sets the tone, and best of all, every dollar stays with local makers.

Date: Nov. 29
Time: 3–8 p.m.
Cost: Free
Location: HOSTE, 1857 W. 16th St.
More Info: tixtree.com 

Snag a deal at Andersonville's Small Business Saturday.
Andersonville's 16th Annual Small Business Saturday offers serious deals from both well-known and hidden gems along Clark Street. From Alamo Shoes to folk art galleries, participating shops are offering discounts, free gift cards, and bonus items. It's also the perfect time to step into cozy restaurants or cafes for a post-shop drink or a treat.

Date: Nov. 29
Time: Various Times
Cost: Free
Location: Various Locations
More Info: andersonville.org 

Get festive at Sheraton's Sleigh Bar.
Step into a holiday dream at the Sheraton's Sleigh Bar, a winter pop-up inside the Sheraton Grand on the Riverwalk. The space is transformed into a cozy sleigh-themed retreat: think twinkling lights, nostalgic décor, and photo ops with Santa. Guests can sip festive cocktails, nibble on seasonal bites from Shula's Steak House, and soak in the holiday spirit with live music or family-friendly activities.

Date: Nov. 29
Time: 5:30–9:30 p.m.
Cost: $5 Suggested Donation
Location: Sheraton Grand Chicago Riverwalk, 301 E. North Water St.
More Info: event.marriott.com