Skip to contents

Local Shops Across Chicago Host Events For Small Business Saturday

With deals, pop-ups, holly jolly trolleys, tree lightings and free Gluehwein, independent shops are the places to be Saturday.

The holly jolly trolley in Ravenswood and tree lighting in Lincoln Square.

CHICAGO — Small Business Saturday 2021 makes it easy to shop for the loved ones on your holiday list while supporting local businesses in your neighborhoods.

Local retailers across the city are offering deals and special events on the day, from Holly Jolly Trolleys that take people to their favorite shopping spots, to gift sets and free holiday cocktails.

Block Club Chicago gathered some events in this guide. Did we miss one? Email us at

Here’s where you can shop:

Live Love Shop Rogers Park

What: Rogers Park Business Alliance is launching its annual holiday rebate program. Dozens of independent shops will offer discounts and promotions. Those who shop at four or more independent stores in Rogers Park can earn up to $75 in cash rebates. The event will feature live music, refreshments, and pastries.

Beginning on Saturday, and through the holiday season, a self-guided outdoor walking tour Walk Chalk Howard Street will also be available featuring interactive art by Chicago 3D artist Nate Baranowski, displayed at the storefront windows of various businesses throughout the neighborhood.

Where: In front of The New 400 Theaters, at 6746 N. Sheridan Road

When: 10 a.m.-2 p.m., Nov. 27

Ravenswood Holly Jolly Trolley

What: The Greater Ravenswood Chamber of Commerce is encouraging local shopping with the help of four trolleys. They’ll offer free rides throughout the neighborhood connecting people to its small businesses that will have promotions, sales, and events for the day. Gnome Brew is offering discounts on equipment and recipe kit combos, KOVAL is offering a 10% discount on all items, and many more.

Further details and promotions are available here.

Where: Stops located along Damen, Montrose, Wilson, Irving Park, and Ravenswood Avenue. The route map with all stops is available here.

When: 11 a.m.-5 p.m., Nov. 27

Caroling, Coca, Shopping, And Tree Lighting in Lincoln Square

What: The Lincoln Square Ravenswood Chamber of Commerce is hosting an event to highlight the local businesses of the area.

While enjoying the deals and the promotions of the small shops in Lincoln Square, the visitors will have the chance to listen to Victorian caroling, with 30-minute performances at the top of every hour. At the end of the day the tree in Lincoln Square will light up, and visitors will be able to enjoy free cocoa and Gluehwein.

More details and a list of promotions is available here.

Where: Giddings Plaza, at 4733 N. Lincoln Ave.

When: Victorian Caroling 11 a.m.-4.30 p.m., Lincoln Square Tree Lighting at 5.30 p.m., on Nov. 27.

Holiday Pop Ups in Albany Park

What: Small businesses in Albany Park, Irving Park, and North Park are offering deals in retail, food, and spirits. But to kick off Small Business Saturday Albany Park is hosting three holiday pop ups where to find additional gift ideas, including handmade crafts, clothing, jewelry, skincare, art, and furniture.

Further details about the event can be found here.

Where: The holiday pop ups will be at 4637 N. Kedzie Ave., 4747 N. Sawyer Ave., and 4730 N. Kimball Ave. 

When: The three holiday pop ups will start at 11 a.m. on Saturday, Nov. 27.

Boxville Soul Holiday in Bronzeville

What: Build Bronzeville is hosting its first Soul Holiday celebration in a series of holiday markets. The markets will feature local vendors for Christmas shopping. During the first appointment there will be live music, while during the other two dates there will be the chance to take pictures with Santa.

Where: Boxville, at 350 E. 51st St. and Black Wall Street Journey Gallery,

When: 12 p.m.-4 p.m., on Nov. 27, Dec. 4, and, Dec. 11

Free holiday cocktails and a Stromboli-making tutorial in Lakeview

What: Get in the Kitchen is offering free holiday cocktails throughout the day. Guests will also have the chance to attend learn how to make Stromboli, similar to pizza rolls. Visitors can pop in at any time to make Stromboli while supplies lasts.

Where: Get in the Kitchen, 3617 N. Broadway

When: 10 a.m.-5 p.m., Nov. 27

Portage Park And Six Corners Holly Jolly Trolley

What: The Six Corners Chamber of Commerce is offering a Holly Jolly Trolley to shop locally. Visitors can grab a passport from the chamber’s office and then stroll any of 20 Six Corners businesses to collect stamps.

The holiday trolley will stop at every block of the shopping district. Those who collect 10 stamps will get a $10 gift card and those who collect 15 might win a $500 gift card. The event will also feature breakfast with Mrs. Claus at Eggsperience, and a winter wonderland decoration at City News Cafe.

Where: The passport will be available at 4054 N. Milwaukee Ave. The breakfast will be at 4925 W. Irving Park Road, and the winter wonderland decorations at 4018 N. Cicero Ave.

When: The Holly Jolly Trolley will run 11 a.m.-4 p.m., Nov. 27. The winter wonderland decoration at City News Cafe 9 a.m.-11 a.m., Nov. 27.

West Town Holiday Bundles

What: The West Town Chamber of Commerce is offering the chance to gift items from small businesses in neighborhood in one, assembled package. Each gift set will feature items from five or more businesses. The value of the packages is $140, but they’ll be sold for $75 each, while supplies last. Bundles are available for purchase here.

Where: Chicago Makers Pop Up Shop West Town location at 1821 W. Chicago Ave.

When: The gift sets can be bought online starting on Nov. 27and they’ll be available for pick up Dec. 15-23

Small Business Saturday in Washington Park

What: The Washington Park Chamber of Commerce is inviting people to shop from local businesses with a kickoff event at the new restaurant Park Supper Club. The event will feature some of the local businesses, including Creativiti Customs Designs, Iceboxx, Lims Beauty Supply, SDL Photography, and Wright Solutions Fingerprinting.

Where: Park Supper Club, at 65 E. Garfield Blvd.

When: From 5 p.m., on Nov. 27

Shop Small in Andersonville

What: Nearly 30 Andersonville businesses will have special deals on Small Business Saturday. While many businesses will hold in-person shopping hours, customers are encouraged to shop online, according to the Andersonville Chamber of Commerce. More details and a list of promotions is available here.

Where: All around Andersonville

When: Nov. 27

Subscribe to Block Club Chicago, an independent, 501(c)(3), journalist-run newsroom. Every dime we make funds reporting from Chicago’s neighborhoods.

Click here to support Block Club with a tax-deductible donation.