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15 Things To Do In Chicago This Weekend: Ugly Sweater Bar Crawl, Pocket Con And Holiday Markets

Ring in winter with festivities across the city, from trolley rides and tree lightings to sing-alongs and gingerbread house parties.

The Andersonville Holiday Trolley will help move shoppers along Clark Street for Late Night Andersonville.
Andersonville Chamber of Commerce
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CHICAGO — You can celebrate the first weekend of December with gingerbread houses, toy drive parades, ugly sweater parties and more.

Here are 15 festive things to do in Chicago this weekend:

Andersonville Winter Market

5-9 p.m. Friday, 10 a.m.-7 p.m. Saturday and 11 a.m.-5 p.m. Sunday

Catalpa Avenue and Clark Street

This market will transform Catalpa Avenue into a holiday market with more than 30 vendors, a holiday trolley and photo opportunities with Santa. See the full list of vendors online.

Ugly Sweater Party

7:30-10:30 p.m. Friday

Emerald Isle, 6686 N. Northwest Highway

“Chicago’s Bravest Stories,” a podcast honoring firefighters and paramedics in the area, is hosting an ugly sweater party. All proceeds will go to providing toys to children at Lutheran General Hospital and Advocate Children’s Hospital. There will be beer, wine, well drinks and light appetizers. You can buy a ticket for $60 online or $65 at the door.

Hyde Park Holly-Day Celebration

10 a.m.-6 p.m. Saturday

5235 S. Harper Court

There will be ice-carving demonstrations, free family photos with Santa and Mrs. Claus, holiday crafts, dance performances, live reindeer and more at this free, day-long fest.

West Town Winterfest

11 a.m.-6 p.m. Saturday

Tours start at West Town Bakery & Diner, 1916 W. Chicago Ave.

Shop local in West Town and take a “Jolly Trolley” guided tour at this annual holiday shopping event. Trolley tickets are available for $20 online.

You can catch this holiday trolley at dozens of local businesses this weekend.

Northwest Side Holiday Trolley

Noon-5 p.m. Saturday

Six Corners Association, 4041 N. Milwaukee Ave.

You can visit more than 30 small businesses on the holiday trolleys, which will run every 15-20 minutes.

Pocket Con

Noon-6 p.m. Saturday

Chicago Cultural Center, 78 E. Washington St.

Pocket Con is a free comic convention that celebrates characters and creators of color, as well as indie, small press and self-published authors. This free, single-day convention reflects on the history of race and gender portrayal in comics and films. Young creators and attendees are also encouraged to produce and submit their own work in contests at the convention.

Ugly Sweater Bar Crawl

3-10 p.m. Saturday

Gold Coast Social, 7 W. Division St.

Put on an ugly sweater and dance around popular River North bars and nightclubs, including Gold Coast Nightclub, Rock Bottom Bar, Underground Nightclub, Bounce Nightclub, Joy District Nightclub, Hubbard Inn and more. Tickets starting at $25 are available online.

Midwinter Market

Noon-7 p.m. Saturday

Kimball Arts Center Chicago, 1757 N. Kimball Ave.

You can shop from local artists and makers and enjoy seasonal drinks and food at this holiday event. Admission is free, but attendees are encouraged to RSVP online.

Pop-Up Sip & Shop

6:30-8 p.m. Thursday

The Silver Room, 1506 E. 53rd St.

There will be gratitude exercises, giveaways and a DJ set.

Gingerbread House Mini Build Party

4-7 p.m. Saturday

Budweiser Brickhouse Tavern, 3647 N. Clark St.

Enjoy pizza, music, raffle prizes and more at this gingerbread house-making party benefitting Habitat Chicago. Tickets for $5-$45 online. Gingerbread house kits are bought separately.

Toys For Tots Motorcycle Parade

9:30 a.m.-4 p.m. Sunday

Dan Ryan Woods on 83rd Street and Western Avenue

Thousands of motorcyclists will ride through the city’s streets in “the world’s largest motorcycle parade” to collect toys for children in need. Those interested in riding in the parade must bring one new, unwrapped toy to donate, and each motorcycle must be street-legal. There is also a meeting 7 p.m. Friday with more information about this 45th annual event.

Credit: Provided
You can enjoy coffee, donuts and cars at this toy drive for children in need.

Toy Drive, Drive

8-10 a.m. Saturday

Midwest Performance Cars, 2105 W. Fulton St.

This toy drive kicks off 8 a.m. with coffee and doughnuts. There will also be a toy collection — unwrapped, and no plush toys — for the Marine Toys for Tots Foundation. You can reserve a spot for free online.

Chicago French Bulldog Rescue’s Ugly Sweater Party

Noon-3 p.m. Saturday

Rizzo’s Bar & Inn, 3658 N. Clark St.

Grab an ugly sweater and your dog for this ugly sweater party to help raise money for Frenchies in need. There will be silent auctions, photo opportunities and a $20 wine pull. There will also be food, drinks and a prize for the “best dressed” attendee. You can buy a ticket for $35 online.

Holidays Around Navy Pier Artisan Market

Noon-8 p.m. Friday-Sunday

Navy Pier, 600 E. Grand Ave.

There will be free workshops, live art viewings and more than 30 small businesses to shop from this weekend through Dec. 18.

Millennium Park Holiday Sing-Along

6-7 p.m. Friday

Millennium Park, 201 E. Randolph St.

Celebrate the holidays and sing along with local music groups, including the Oakdale Christian Academy Choir and Windy City Gay Chorus and Treble Quire. There will be sing-alongs Fridays through Dec. 16.

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