Series · Every Monday at 20:00

Musical Monday: Show Tunes

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

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Mon, Sep 21 · 8:00 PM

In 4 weeks · Monday, September 21, 2026

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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.

Ran 4 times since July — see past dates

Mon, Aug 17
Mon, Aug 10
Mon, Aug 3
Mon, Jul 27

Every date in this series runs the same way. Back to the series

More Events at Sidetrack

Showing 6 upcoming events

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.

Sapphic Saturday

Saturday, August 29th, 2026

5:00 PM

The last Saturday of every month belongs to the lesbians and lesbian lovers at Sidetrack. No cover gets you into a celebration across the Main, Cherry, and North bars with queer women's anthems, drag performances, games, and a room full of people who show up for sapphic joy. It's the kind of event that feels like coming home.

More LGBTQ+ Events in Chicago

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Sunday After Dark

Sunday, August 23rd, 2026

10:00 PM

Every Sunday night after 10pm, Hydrate shifts into high gear with a rotating mix of throwbacks, hip hop, and today's hottest hits. VJ George G keeps the visuals sharp while the dance floor fills up with people who know how to make a Sunday night count. No cover, cheap Bud Lights, and a room that gets better as the night goes on.

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.

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