Series · Every Sunday at 15:00

Sunday Funday Show Tunes

Sidetrack3349 N Halsted St, Chicago, IL 60657Directions(773) 477-9189Website

Next up

Sun, Aug 30 · 3:00 PM

In 1 week · Sunday, August 30, 2026

Upcoming dates

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.

Ran 4 times since July — see past dates

Sun, Aug 23
Sun, Aug 16
Sun, Aug 9
Sun, Jul 26

More Events at Sidetrack

Showing 6 upcoming events

Musical Monday

Monday, August 24th, 2026

8:00 PM

Show Tunes all night long — the kind of sing-along that turns strangers into a chorus. Sidetrack's Monday tradition pairs Broadway classics with party energy, open from 3pm through 2am so you can show up whenever the mood strikes.

Trivia Tuesday with Stew

Tuesday, August 25th, 2026

8:00 PM

Test your pop culture knowledge with Stew hosting trivia at Sidetrack, then stick around for Pop Favorite Videos spinning until 2am. It's the kind of Tuesday night that actually gives you a reason to show up — smart questions, good company, and the rooftop energy that makes this place legendary.

All Things Dua & Ari

Wednesday, August 26th, 2026

9:00 PM

Ariana Grande Week kicks off with a night built for the people who know every word and aren't afraid to show it. Get on stage, show your moves, win prizes, and dance through the night with rotating drag performers. This is the kind of sing-along energy Sidetrack does better than anywhere else.

All Things K Pop

Thursday, August 27th, 2026

9:00 PM

K-pop takes over Sidetrack's Main, Cherry, and North Bars for a night built for fans who know every word, every dance break, and exactly which member is their bias. Expect a packed crowd, high-energy music, and the kind of singalong energy that only happens when you're surrounded by people who genuinely love this stuff.

Let's Go! Latin Thursday

Thursday, August 27th, 2026

9:00 PM

Sidetrack's weekly Thursday night party takes over the Main, Cherry, and North Bars with high-energy Latin beats, DJ-driven dance floors, and a crowd that knows how to move. Expect a packed dance floor, strong drinks, and great vibes — the go-to Thursday escape for anyone who wants to dance to Latin rhythms without the pretense. Occasional themed editions swap in pop music videos and special guest hosts.

Post Brunch Fun

Saturday, August 29th, 2026

1:00 PM

The Saturday afternoon shift at Sidetrack — when brunch hangs on and the dance floor starts calling. Grab a drink, catch up with friends, and ease into the weekend vibe before things really heat up. It's that sweet spot between lazy brunch energy and full-on nightlife, with good music, good people, and a rooftop if you need air.

More LGBTQ+ Events in Chicago

Discover more events happening around Chicago

Chicago House TransSafe Drop In

Monday, August 24th, 2026

2:00 PM

A free, judgment-free weekly drop-in for trans and non-binary folks at Center on Halsted. No appointment needed — just show up and connect with real, practical support including housing navigation, employment services, legal help with name changes and discrimination cases, medical referrals, and more. As the Midwest's first comprehensive one-stop resource designed specifically for the trans community, TransSafe connects you with people and resources that actually understand what you're navigating.

Make Mondays Suck Less

Monday, August 24th, 2026

5:00 PM

Monday nights at SoFo Tap are built for people who need to shake off the work week—$5 You Call It drinks, 90s and 2000s music videos on rotation, and a room full of folks who get it. Free entry, open till 2am. Comfort, nostalgia, and easy vibes, every single week.

Your Friend Rachel x The God Awful Small Affairs

Monday, August 24th, 2026

7:00 PM

Two queer musicians, one intimate night underground. Brooklyn's Your Friend Rachel brings her distinctive sound to Dorothy's subterranean stage, sharing the bill with Chicago's The God Awful Small Affairs. Live music for people who actually listen — expect the kind of performance that reminds you why you showed up in the first place.

Squabble Trivia

Monday, August 24th, 2026

7:30 PM

Monday nights at 2Bears belong to Squabble—a fast-paced, feud-style game night where teams compete, laugh, and maybe argue a little along the way. Hosted by Pup Figaro, it's the kind of free, unpretentious fun that keeps people coming back. Show up, grab a team, and settle in for two hours of the kind of chaos that only works in a room full of people who get it.

Mondays are Ruff

Monday, August 24th, 2026

10:30 PM

Mz Ruff 'N Stuff brings the heat every Monday night at Hydrate — a rotating lineup of fabulous queens and one iconic entertainer who knows how to keep the party going. Doors at 8pm, show at 10:30pm, $5 cover, and beats by MARTIN. The perfect way to reset your week.

Serve! Vocal Edition Karaoke

Monday, August 24th, 2026

11:00 PM

Late-night karaoke where pop stars and divas take over the stage—hosted by Tyler Hall, Tyler Meyer, and Andrew every Monday from midnight to 3:30am. Free, no cover, just show up ready to sing and own it.

Never miss Sunday Funday Show Tunes

Get reminders, save events, and find more LGBTQ+ happenings in the Gathry app.