Community Focused · Chicago

Santa Speedo Run Northalsted 2026

Name: Santa Speedo Run Northalsted 2026
Start: 2026-12-05
Location: Sidetrack

Sidetrack

3349 N Halsted St, Chicago, IL 60657

directions(773) 477-9189website

Coming up

Sat, Dec 5

Saturday, December 5, 2026

Times on venue site

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About

The Santa Speedo Run is back for its 15th year, and the whole crowd comes out in festive, very little clothing to run through Northalsted. Saturday, December 5th at Sidetrack in Chicago's Boystown, so grab your Santa hat and your nerve. Expect a rowdy good time with the neighborhood cheering you on.

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More Events at Sidetrack

Showing 6 upcoming events

rooftop

T.g.i.f. Show Tunes

Friday, November 13th, 2026

4:00 PM

Kick off your weekend at Sidetrack's legendary Friday show tunes sing-along! Every other Friday, the rooftop and video bar come alive with a crowd that knows every word to their favorite Broadway classics and pop standards. Grab a drink, catch the sunset, and get ready to belt out the hits with fellow show tune lovers in the kind of communal, joyful singing that makes this Chicago tradition legendary.

Drag Shows

Ruck & Maul 2026

Saturday, November 14th, 2026

6:00 PM

The Chicago Dragons Rugby Football Club brings their biggest fundraiser of the year to Sidetrack—a drag-fueled night that blends two communities in the best way possible. Expect drag performances, a packed dance floor, and the kind of energy that comes when athletes and performers show up for the same cause. All proceeds support the Dragons.

Showtunes

Sunday Funday Show Tunes

Sunday, November 15th, 2026

3:00 PM

Sidetrack's legendary Sunday afternoon tradition — the whole room singing along to Broadway classics and pop standards across the Main, Cherry, and North Bars. It's the kind of joyful, communal sing-along that makes strangers harmonize together, with rooftop and video bars packed with people who know every word. A weekly ritual that's become the neighborhood's favorite reason to start the weekend early. Arrive early, bring your voice, and settle in for an afternoon of pure theater magic.

Dance Party

Musical Monday: Show Tunes

Monday, November 16th, 2026

8:00 PM

Every Monday, Sidetrack turns into Chicago's ultimate show tunes sing-along. Broadway classics and movie musicals play on the big video screens while a room full of people who know every word belts along together. It's a beloved weekly tradition blending theater-kid energy with dance party vibes — come whenever the mood strikes and stay for the chorus of strangers turned friends.

Trivia

Trivia Tuesday: Pokémon Edition

Tuesday, November 17th, 2026

8:00 PM

Trivia Tuesday goes full Pokémon at Sidetrack on Chicago's Halsted Street, where you'll put together a team or play solo to take on the trivia questions. It's a fun, low-pressure way to test your knowledge in one of the city's legendary video bars.

Music Videos

All Things Gaga

Wednesday, November 18th, 2026

Times on venue site

All Things Gaga at Sidetrack is the third Wednesday monthly night where you live for the applause and dance along to all your favorite Lady Gaga music videos. Expect a Perfect Illusion drag performance and a room full of fans who know every choreographed move. It's a Chicago Halsted Street classic for Gaga lovers.

More LGBTQ+ Events in Chicago

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Late Night

Sativa's Hot Boxxx

Thursday, November 12th, 2026

11:00 PM

Hydrate Nightclub

Sativa's Hot Boxxx is a late-night drag show at Hydrate in Chicago's Boystown, where Sativa Diamond hosts Kara Mel D'Ville, Howdy Rowan and Judith Priest for an hour-and-change of camp and high-energy fun. It's on Thursday, November 12, from 11 PM to 1 AM, and there's no cover, so you can roll in without the door math. Grab the $12 TT Baby drink special and get settled in for a night you won't see coming.

Drag Shows

Oops We Did It Again: Y2K Drag Dinner

Friday, November 13th, 2026

Times on venue site

Kit Kat Club

Oops We Did It Again is a Y2K-themed drag dinner at Kit Kat Club, Chicago's original drag show lounge in Lakeview on Halsted Street. Pull out your frosted tips and butterfly clips, settle in for an elevated dinner by Chef Chelsea Poe, and watch the Kit Kat Divas take the velvet stage. It kicks off Friday, November 13 at 7pm, so you'll want to book a table early.

Happy Hour

Queer Happy Hour @ Nightshade & Dark

Friday, November 13th, 2026

7:00 PM

LGBTQ+ Center Lake County

A Friday night gathering for queer folks to eat, drink, and connect in a genuinely welcoming space. No pretense, no pressure — just good company and a chance to be yourself. 21+.

Live Music

Dusky Waters: The Mother Magnolia Tour Live

Friday, November 13th, 2026

7:00 PM

Dorothy

New Orleans singer-songwriter Dusky Waters brings her ancestral Americana to Chicago for an intimate trio night at Dorothy, the 70s-inspired lesbian speakeasy in West Town. Expect close-up storytelling and rich harmonies in a room built for listening. Doors open at 7pm and the set runs till 8:30pm, so you'll have time for a nightcap after.

Trivia

Are You Smarter Than a Drag Queen?

Friday, November 13th, 2026

7:00 PM

2Bears Tavern Uptown

High-energy drag trivia night hosted by Tia Pet at 2Bears Tavern Uptown. The questions are tricky, the host is shady, and the room is completely out of control—in the best way. Gather your team and test your wits over three hours of comedy, competition, and chaos. Free to play, no cover, drinks flowing, and the perfect way to kick off a Friday night at this neighborhood bar. Every Friday from 7pm to 10pm.

Karaoke

Artemis Singers Karaoke Fundraiser Party

Friday, November 13th, 2026

7:00 PM

Whiskey Girl Tavern, 6318 N Clark St, Chicago, IL, 60660

Artemis Singers, Chicago's all-volunteer lesbian feminist chorus, is throwing a karaoke party at Whiskey Girl Tavern on Clark Street in Chicago's Edgewater neighborhood. Grab the mic, grab a drink, and support 46 years of community singing: 100% of net proceeds go straight to the chorus. All ages until 9 PM, 21+ after. Food and drinks are for purchase, and there are pay-what-you-wish baked goods.