15 Things To Do In Chicago This Weekend: Small Business Saturday, World Cup Watch Parties And Holiday Fun


CHICAGO – There’s plenty to do throughout the city this weekend, including World Cup watch parties, music festivals, and local street markets.

Here’s a roundup of 15 things to do in Chicago this weekend:

Holly Jolly Trolley Rides

Starts Saturday at 11am

Various locations

There will be Holly Jolly Trolleys in neighborhoods across the city for Small Business Saturday, including in Ravenwood And Bucktown.

Friday 17-22

Rizzo’s Bar & Inn, 3658 N. Clark St.

This Santa’s party bus is rolling into town this weekend and well into December. The five-hour experience includes a chili and mac and cheese buffet, a bus tour, and admission to Lincoln Park ZooLights and Christkindlmarket. Tickets for this BYOB bus ride start at $49 and are available on line. Cyclists must be 21 years of age or older and have a valid ID.

4pm-1am Friday-Monday

Lucky Strike, 322 E. Illinois St.

This Thanksgiving weekend, head to the bowling alley. If you flip a turkey — three shots in a row — Lucky Strike will donate $50 to the Greater Chicago Food Depository.

Saturday from 10:00 to 14:00

The Common Cup, 1501 W. Morse Ave.

Kick off the holiday shopping season and support local businesses this weekend for #SmallBizSat. There will be a welcome station from 10am to 2pm with complimentary crepes, coffee and cocoa, live music, a selfie station, bags and a business roster offering specials throughout the day.


Various locations in Lincoln Square

Make small purchases at companies offering special discounts and enjoy the festivities throughout the day, including photos with Santa and Christmas tunes from the Victorian Carolers. You can also end the day with the lighting of the Lincoln Square Ravenswood Chamber of Commerce tree at 5.30pm

Saturday from 10:00 to 17:00

Absolutely everything essential, 3521 S. King Drive

There will be more than 20 artists, designers, small business owners, vendors and essential service providers at Bronzeville’s largest Small Business Saturday event. You can ‘make and take’ your own handmade gifts or shop for locally made clothing, jewelry and accessories, treats and more.

Credit: Quinn Myers/Block Club Chicago
Midwest Coast Brewing, 2137 W. Walnut St. on April 29, 2022

Friday 5-5pm

Various locations in Chicago’s beer district

Shop from 35 local producers this Black Friday with a drink in hand. There will be a variety of handmade products, including jewelry, home decor, prints, soap, paintings, candles, and more. Admission is free.

18-19 Friday

Millennium Park, 201 E. Randolph St.

Celebrate the holidays and sing along with local bands, including the Oakdale Christian Academy Choir and Windy City Gay Chorus and Treble Quire. If you don’t make it this weekend, there will be singing from Friday until December 16th.

10am-4pm Friday-Sunday

National Museum of Mexican Art, 1852 W. 19th St.

This holiday flea market features handmade Mexican keepsakes, including ornaments, nativity scenes, T-shirts, jewelry, and more. Museum members will receive 30% off all merchandise.

Credit: Provided
This will be the city’s third annual Albanian Independence Parade.

Albanian Independence Day Parade

Sunday 12:30-14:30

900 S. Columbus Drive

You can celebrate the Albanian Independence Day with the Albanian-American community in this parade.

World cup watch parties in a pub

1pm Friday and 1pm Saturday

Broken English Taco Pub, 75 E. Lake St., 2576 N. Lincoln Ave and 1400 N. Wells St.

You can tune in United States versus England And Mexico versus Argentina play together with fellow Chicagoans and enjoy $40 margin pitchers.

1pm Friday

Gallagher Way, 3635 N. Clark St.

You can also tune in to the USA vs England match at Gallagher Way. Afterward, you can stop by Christkindlmarket Wrigleyville for international food and drink.

Credit: Provided
You can take pictures with Santa every weekend from November 25th to December 18th.

15-20 Friday and 11-17 Saturday-Sunday

Gallagher Way, 3635 N. Clark St.

Santa is coming to Lakeview this weekend. He will be there for photos Friday through Sunday until December 18th.

Doors open 5pm Friday-Sunday

Friday-Saturday at Thalia Hall, 1807 S. Allport St.

Empty-Bottle Sunday, 1035 N. Western Avenue.

Hear performances from Psyche, Blu Anxxiety, Boy Harsher, Black Plague and more this weekend. There will also be a photobooth, interactive exhibits, vendors and more. Tickets costing $41-$176 are available on line.

Friday from 19:00 to 23:00

SPIN, 344 N. State St.

Watch paint fly and canvases go from “blank to beautiful” in this live art battle. All artwork created during the event will be available for purchase via a silent auction. Doors open at 7pm and painting starts at 8pm You can register to compete here. Spectator tickets are $22 online and $25 at the door. You must have a valid ID with you to enter.

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Written by Natalia Chi

Chicago Popular; Chicago breaking news, weather and live video. Covering local politics, health, traffic and sports for Chicago, the suburbs and northwest Indiana.

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