PHOTOS: Speedo-clad Santas made Chicago’s yuletide gay

Over the weekend, the Santa Speedo Run returned to Chicago, and the scantily clad Kris Kringles of Boystown were packing plenty of packages.

Dec 9, 2023 - 19:00
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PHOTOS: Speedo-clad Santas made Chicago’s yuletide gay
Men in the MainBar.

Over the weekend, the Santa Speedo Run returned to Chicago, and the queer Kris Kringles of the Second City were packing plenty of packages.

Founded by husbands Karl Sponholtz and Jeff Colgan in 2011, this scantily-clad fun run has attracted hundreds of participants every year to raise funds for the Center on Halstead, the Midwest’s most comprehensive LGBTQ+ community center. Donning skimpy swimsuits and Santa hats (and not much else), this year’s runners raised nearly $140,000 that will go towards anti-violence, queer youth, and elder services.

Starting at host venue Sidetrack, the 2022 winner of the Best of Gaycities “#1 Nightclub” award, these pantsless Père Nöels jogged through the heart of Chicago’s West Lakeview neighborhood. Cheered on by both spectators and members of the Chicago Spirit Brigade, red-nosed runners pranced down Halstead Street, then diverged into a choice between two predetermined circuits before looping back for Sidetrack’s Santa Speedo Run afterparty. After getting nipped so hard by Jack Frost, these runners deserved to warm up with some Jack ‘n Cokes.

Sidetrack’s aprés-run was presided over by local drag darling Debbie Fox and featured gay notables such as muscly musician Steve Grand. The event decked the various halls of the venue, such as the MainBar, GlassBar, NorthBar, and Entryway, which sported a candy cane-colored step-and-repeat for posing Pancers and Vixens.

Beyond the holiday hijinx, the Santa Speedo Run is a prominent gift giver for Chicago’s LGBTQ+ community. Since its inception over a decade ago, this risque fundraiser has generated over $500,000 for the Center on Halstead. Its numerous programs and services include Lavender Living, a support group for queer young adults, the Youth Horizons mentorship program, and the Ralla Klepak Performing Arts Program, to name a few. For Chicago’s queer communities, the Santa Speedo Run is the gift that keeps on giving all year round.

For those who missed the festivities, we’ve snatched some of the nicest and naughtiest moments from this year’s Santa Speedo Run. Ho ho ho, you hos!

Sidetrack manager Bradley Thomas making announcements and explaining rules of Santa Speedo Run
Sidetrack manager Bradley Thomas makes announcements and explains the rules of the race.
Runners began after 2 p.m. on Saturday December 2, 2023
Runners began after 2 p.m. on Saturday, December 2, 2023
Participants could turn either left or right when exiting the front doors of Sidetrack
Participants could turn either left or right when exiting the front doors of Sidetrack.
The runners covered the Halsted Street area for their route.
The runners covered the Halsted Street area for their route.
A Santa Speedo Run around the block
A Santa Speedo Run around the block.
Chicago Spirit Brigade cheering on the runners.
Hostess Debbie Fox on her throne.
Hostess Debbie Fox sitting on her throne like a true Christmas Queen.
Ho ho host
Ho ho hosting hotties.
Picking up a Fox named Debbie.
Picking up a Fox named Debbie.
Tito's Vodka team at Santa Speedo Run

Tito’s Vodka team at the Santa Speedo Run afterparty.

Tito's Vodka pop-up at Santa Speedo Run
Tito’s Vodka pop-up.
Three Kings in the GlassBar for Santa Speedo Run
Three Kings in the GlassBar.
The Three Wise Men at Santa Speedo Run.
The Three Wise Men.
The Santa Speedo Run team raised over $140,000 in 2023.
The Santa Speedo Run team raised over $140,000 in 2023.
Sidetrack manager Bradley Thomas and Rey Rodriguez at Santa Speedo Run party
Sidetrack manager Bradley Thomas and Rey Rodriguez.
Sidetrack GlassBar for Santa Speedo Run
The Sidetrack GlassBar.
Rooftop DeckBar at Sidetrack was chilly and delightful with Casey Travis Kimpel and Roman Harrington at Santa Speedo Run
Rooftop DeckBar at Sidetrack was chilly and delightful with Casey Travis Kimpel and Roman Harrington.
Overlooking MainBar of Sidetrack
Overlooking MainBar of Sidetrack.
Open air Rooftop and DeckBar with staff of Sidetrack
Open-air Rooftop and DeckBar with staff of Sidetrack.
Men in the MainBar.
Men in the MainBar.
Kissing under the mistletoe.
Kissing under the mistletoe.
Group enjoying the Rooftop DeckBar.
Group enjoying the Rooftop DeckBar.
Fur covered friends
Fur covered friends.
Elves named Dougie, Will, Mike and Brandon.
Elves named Dougie, Will, Mike and Brandon.
Drinking in the CherryBar.
Drinking in the CherryBar.
Couple caught by the Entryway.
Couple caught by the Entryway.
Corner Step and Repeat opportunity.
Corner Step and Repeat opportunity.
Cocktails in the CherryLounge
Cocktails in the CherryLounge
Calvin Kleins and candy canes.
Calvin Kleins and candy canes.
Birdseye view at the Rooftop DeckBar
Birdseye view at the Rooftop DeckBar
Antonio Viviano and friend
Antonio Viviano and friend.

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