Ah, the ugly sweater – that quirky, often colorful piece of clothing buried deep in the back of our closets, loaded with memories and the promise of someday making a public appearance. We all have one, right? It might be a relic from a long-forgotten holiday party or a gift from Grandma that, despite its, well, unique aesthetic, holds a special place in our hearts. But fear not, fellow Chicagoans, for the time has come to dust off those fashionably challenged gems and let them see the light of day! The 3rd Annual Ugly Sweater Crawl is back, and it’s calling all brave souls to proudly don their most cringe-worthy knitwear.

3rd Annual Ugly Sweater Crawl Is Organized By Makers Mark

Presented by the good folks at Makers Mark, this fun and festive event promises a day of laughter, camaraderie, and, of course, the chance to win the coveted title of having the ugliest sweater in the Windy City.

Set to take place on Saturday, December 2, from noon to 8 pm CST, at the fabulous Kitchen + Kocktails in Chicago, this crawl is not just an event; it’s a celebration of the sweaters we love to hate. Last year, over 500 of Chicago’s finest embraced the spirit of the season and joined in the festivities. And this year, the organizers are pulling out all the stops with a massive prize awaiting the lucky soul with the ugliest sweater.

The day kicks off with a brunch at Kitchen and Kocktails from 11:30 am to 1:00 pm, setting the stage for the sartorial spectacle ahead. This is not just a meal; it’s a prelude to the adventure that awaits, and it’s where you’ll pick up your all-important wristband – your ticket to a day of unapologetic sweater flaunting.


Get Early Access To The Event With VIP Tickets

For those with VIP tickets, the fun begins even earlier at 1:30 pm, as the trolley departs to the South Loop, the first stop in a whirlwind tour of Chicago’s most happening spots. From 12 pm to 4 pm, the Ugly Sweater Crawl headquarters at HUE Chicago, located at 67 E. Cermak, will be buzzing with activity as participants pick up their wristbands and prepare for the journey.

3rd ugly sweater crawl chicago

The South Loop locations from 2 pm to 6 pm promise undisclosed delights, keeping attendees on their toes as they hop from one spot to another, proudly showcasing their questionable taste in knitwear. And let’s not forget the mysterious South Loop location from 8 pm to 10 pm – a perfect opportunity to cap off the day with more sweater-induced revelry.


For the true party animals holding VIP tickets, the night continues at the after-party at HUE Chicago from 7 pm to 11 pm. While the DJs for the event are yet to be announced (TBA), rest assured that the beats will be as lively and eclectic as the sweater choices on display.

Tickets for this unforgettable day range from $20 to $50, offering options for every budget. So, mark your calendars, dig out that ugly sweater you’ve been avoiding, and get ready to make a bold fashion statement at the 3rd Annual Ugly Sweater Crawl. After all, it’s not about looking good; it’s about having a great time and creating memories that will make you smile – even if your sweater doesn’t.


So, see you there, Chicago, in all your ugly sweater glory! And, while you rush to find your ugly sweater, do not forget to check out Urban Matter for more on the latest events in Chicago!


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