
2Bears Tavern Uptown
Uptown
$5 premium well cocktails and $8 Wynks, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Wells + WynksHappy hours, specials & events
Schedules change — always check with venues before heading out.

Uptown
$5 premium well cocktails and $8 Wynks, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Wells + Wynks
Uptown
$3 house shots and $8 house cocktails, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Shots + cocktails
Uptown
$5 premium well cocktails, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Premium wells
Uptown
$6 premium well cocktails and $7 signature margaritas, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Margaritas
Uptown
$6 premium well cocktails and $8 Wynks, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Wells + Wynks
Uptown
$6 premium well cocktails and $8 Wynks, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Wells + Wynks
Uptown
$6 premium well cocktails and $7 signature margaritas, alongside daily $5 Jäger, Fireball, and Malört; $4 Old Style, PBR, and Hamm’s; free pinball and darts; and BYOF.
Margaritas
Boystown
Musical Monday brings show tunes and music videos to Sidetrack's big screens all evening.
No regular cover
Boystown
Weekly trivia followed by pop-favorite videos through close; OUTspoken LGBTQIA+ storytelling takes over the first Tuesday each month at 7 PM.
Weekly
Boystown
TGIF Show Tunes on the big screens, followed by the Friday dance party from 9 PM–2 AM.
No regular cover
Boystown
A recurring afternoon of drag and games, followed by Sidetrack’s Saturday Night Dance Party from 8 PM–3 AM.
Drag + dance
Boystown
Sunday Funday Dance Party follows afternoon Show Tunes and party music across the bars.
No regular cover
Andersonville
Darling Specials: Wed–Thu 5–7 PM, Fri 4–6 PM, Sat 2–4 PM, and all day Sunday.
Sunday all day
Andersonville
Nerd Bear Trivia with themed questions, prizes, puns, and free entry at the neighborhood bear bar.
No cover
Andersonville
The SoFo Tap’s weekly flagship bear party. All regular weekly programming is free unless otherwise noted.
No cover
Andersonville
Dog-friendly patio and bar hangout for four-legged guests and their people.
Dog friendly
Andersonville
Sunday hangout with drinks, laughs, and the regular crew; Bearaoke follows later that night.
No cover
Andersonville
Weekly bear karaoke at The SoFo Tap.
No cover
Boystown
$5 Bud Light, $6 red or white wine, $7 well cocktails, plus 25% off starters and appetizers.
Food + drinks
Boystown
Late-night DJ sets and a full dance floor inside The Belmont; check the venue for the week’s DJ and cover.
DJ nightUptown
An intimate upstairs cabaret night with rotating local hosts and performers; bring cash for tips.
Rotating lineup
West Town
$10 Dorothy menu cocktails, $8 spirit-free cocktails, and an $8 rotating dealer’s-choice drink.
No event nightsBoystown
Weekly drag brunch hosted by Queen Batty Davis, with a $50 bottomless mimosas, bubbles, and brunch package; reservations recommended.
Weekly brunch
Boystown
All-day happy hour every Monday at Replay Lakeview.
Every Monday
Boystown
Weekly Mario Kart night at Replay Lakeview.
Weekly
Boystown
Weekly Super Smash Bros tournament.
Weekly
Boystown
Weekly karaoke at Replay Lakeview.
Weekly
Boystown
Weekly Thursday trivia, followed by Thicc Thursdays at 9 PM.
Weekly
Boystown
Weekly late-night Thursday party at Replay Lakeview.
Weekly
Boystown
Weekly Sunday Heat day party at Replay Lakeview.
WeeklyBoystown
Recurring neighborhood bingo in the compact two-level bar; check same-day socials for the host and prizes.
Verify same daySave the date
Two big Chicago weekends worth planning around.
June
The annual parade travels through Uptown, Boystown, and Lincoln Park with community groups, floats, and celebrations across the city.
Pride Chicago ↗August
A two-day street festival along Halsted with live music, drag, food, drinks, local vendors, and packed patios throughout Boystown.
Market Days ↗Sponsored
A discreet spot for happy hours, specials, venue promotions, ticketed events, and local partners—always kept at the bottom of Pocket Gay.
© Pocket Gay 2026