You can flirt over the pool table or buy your date a round of beer without hurting your wallet. Hoping to reel in a few hotties while you’re watching the game? Head to the North End, Chicago’s gayest sports bar. The dancefloor isn’t though, and if you stick around long enough, you’re sure to get in on the action. Progress doesn’t ever turn absolutely crazy until after midnight anyway, so if you’re not looking for that, it’s easy to avoid. Weekends are even better, as they are open in the early afternoon hours. Okay, sure, this place isn’t open until 5 pm on weeknights, but that’s the perfect time to grab a quick after-work drink with a new bae. Photo Credit: Progress Bar Facebook Progress It is kinda weird seeing this giant nightclub pretty dead during the day, but also anticipatory of the night to come. It’s the perfect place to go if you’re looking for a grand old time, but it also has a few quiet hours on the weekends when they open in the early afternoon. Listen, Roscoe’s is definitely a nightclub. Photo Credit: Roscoe’s Tavern Facebook Roscoe’s But if you head bar in Chicago during the afternoon before it gets ridiculously crowded, you’re sure to have a nice time with a few older guys who keep hoping you’ll stay a little longer. The first gay bar and club to ever hit Boystown back in 1975, Little Jim’s Tavern has an extensive history of being the easiest place to snag a man in the later hours of the night. Photo Credit: Little Jim’s on Halsted St. We mean, with a name like that, how could you go wrong? This place gets wild when it starts to venture into the early hours of the morning, but come here in the sleepy hours of the early afternoon and you might be able to call dibs on a cutie as you’re both having the first beer of the night.
Photo Credit: Manhandler Saloon Facebook Manhandler Saloon It’s a classy experience whenever you hit up the Kit Kat Lounge. This upscale gay and lesbian club or lounge in Chicago is relatively small, and the queens glide between booths with the utmost ease, even posing for a picture with you in the middle of their set. You’re definitely going to catch a drag show here, and you’ll have a top-notch seat for it too. Photo Credit: Kit Kat Lounge Facebook The Kit Kat Lounge Host to many queer-friendly events, like women’s comedy and storytelling, Joie de Vine is where Chicago’s finest ladies go for a drink, and damn it if we’d miss out on that. Side note: can we talk about the severe lack of lesbian bars in this city!? Get it together, Chicago. One of Chicago’s few lesbian-owned haunts, Joie de Vine is technically classified as a wine bar, but everybody knows who reigns here. Photo Credit: Joie de Vine Facebook Joie de Vine Second Story Bar has been around for decades, but it’s honestly a great place to grab a drink midday since it’s lesser-known. This cash-only gay bar and club in Chicago is basically a speakeasy for the LGBTQ+ community, except, instead of being subterranean, it’s vertically smushed between a psychic shop and an Armenian restaurant. Read More: 8 Popular Bars You Need to Visit in Boystown Photo Credit: Second Story Bar Facebook Second Story Bar