Chicago gay bar hosts its tenth Santa Speedo Run

The Santa Speedo Run at Sidekick, 2021 (Photo: @priyam_patel/Instagram)

The annual Santa Speedo Run in Boston, now in its third decade, is the best-known such event in the US. However, smaller runs have followed in its wake. Chicago’s Santa Speedo Run Northalsted, organized by partners Jeff Colgan and Karl Sponholtz, is one such get together.

Santa Speedo Run
(Photo: @oneparame/Instagram)

The annual calendar highlight, celebrating its tenth anniversary in 2021, took place last Saturday at beloved gay bar Sidetrack. Those wishing to take part turned up around midday to register.

Santa Speedo Run Northalsted
(Photo: Sidekick)

Santa Speedo Run Northalsted hits the streets

After a rendition of ‘Jingle Balls’, the run began at 2pm. Around 400 participants ran a mile through Lakeview East (where the temperature barely scraped up to 40F). Most wore little more than Speedos and Santa hats.

(Photo: @chicago_tim/Instagram)

A post-run auction of underwear helped generate more dollars, while those wanting to sprint had to raise a minimum of $35 each. In fact, many raised more. One participant, David Roberts, managed a staggering $12,500, which won him some travel vouchers from one of this year’s sponsors, American Airlines.

(Photo: @chicago_tim/Instagram)

In total, around $85,000 was raised (and counting), bringing the total generated over the last ten years to approximately $600,000.

Proceeds from the event go towards The Center On Halsted, the city’s long-running and groundbreaking LGBTQ center.

Santa Speedo Run Northalsted at Sidekick
(Photo: @mikeyv773/Instagram)

If you missed out on the Santa Speedo Run, Sidetrack has a full line-up of regular events and holiday parties over the coming month.

(Photo: @dtor04/Instagram)
The Santa Speedo Run organizers
(Photo: @jeffreycolgan/Instagram)
More of Santa’s little helpers at Sidekick in Chicago (Photo: Sidekick)

Showtunes and musicals dominate the video screens on Sunday afternoons and Monday evenings, while frozen cocktails go down well whatever the temperature outside. Sidekick also holds another big fundraiser on New Year’s Eve for Chicago’s Legacy Project.


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Five other places to visit in Chicago

• The Center on Halsted

The Center on Halsted in Chicago
The Center on Halsted (Photo: Supplied)

Chicago’s LGBTQ hub, the Center on Halsted, is one of the best in the country. It started life way back in 1973 as Gay Horizons and has grown exponentially since that time. It runs a wide range of programs and services for all sections of the community. There’s also a great cafe and exhibition space.

• The Legacy Walk

Two of the pylon's on Chicago's LGBT Legacy Walk
Two of the pylon’s on Chicago’s LGBT Legacy Walk (Photo: The Legacy Project)

Chicago’s LGBTQ neighborhood (recently renamed Northalsted after being known for years as Boystown) has one of the finest memorials to queer history: The Legacy Walk. Part outdoor history installation and part museum, admire the two dozen, 25-foot tall rainbow pylons placed along North Halsted Street. They feature bronze plaques with information about notable activists and figures.

• Roscoe’s Tavern

Roscoe’s Tavern is another long-running bar in the Northalsted neighborhood that’s been serving up camp fun since 1987. Expect plenty of drag entertainment and a very popular weekly drag brunch on Saturdays.

• The Closet


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Dating back to 1978, The Closet on Halsted Street is one of Chicago’s best-known lesbian hangouts (it welcomes everyone and the crowd is quite mixed on most nights). The cozy venue offers a friendly welcome and is a popular post-game meeting point for sports teams during the summer.

• Kathy Osterman Beach

If the thought of wearing Speedos during a Chicago winter fills you with horror, save them for the summer instead and head for Kathy Osterman Beach. Located at the northernmost tip of Lincoln Park, the stretch is sometimes called Ardmore Beach or Hollywood Beach because of its proximity to those streets. Gay people tend to hang out on the south side of the beach in the warmer months.

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