Cabaret

Soul Sundays at 2Bears Tavern Uptown is a Sunday evening soul night in Chicago's Uptown neighborhood, running 6:00 PM to 10:00 PM, just steps from the Wilson CTA station. Put on your best groove, grab a cocktail from the bar, and let the music carry you through the evening. Dog-friendly and easy to reach, it's a low-key way to end your weekend with good company.

Free Texas Hold'em every Sunday night at Meeting House Tavern — no gambling, no stress, just a damn good game night. Whether you're a beginner learning the ropes or a competitive card shark, you'll find a welcoming table full of regulars and new faces alike. Play for prizes, bring a friend for bonus chips, and settle in for cards with people who know how to have a good time. Low-key, social, and exactly the kind of thing that keeps regulars coming back.

Sunday nights at SoFo Tap belong to anyone brave enough to grab the mic. Hosted by Rhett Butlah, Bearaoke is a karaoke night where the energy is high, the crowd is genuinely supportive, and nothing's off limits—country, power ballads, showtunes, whatever you've got. Free entry, 9pm to 1am, in the heart of Chicago's bear bar scene. Just bring confidence and a song in your heart.

Every Sunday night at Hydrate, the party shifts into high gear after 10pm with a rotating mix of throwbacks, hip hop, and today's hottest hits. VJ George G keeps the energy moving and the dance floor packed all night long. No cover charge and $6 Bud Lights make it an easy reason to show up—this is the neighborhood's reliable late-night reset for those who want to keep the weekend going.

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.

The SoFo Tap's weekly Monday reset — log off, shake off the work week, and settle into $5 You Call It drinks while 90s and 00s music videos play all night long. Free entry, low-key neighborhood-bar energy, and open from 5pm to 2am, every Monday.