Chicago's gay community is out and proud, especially in the Boystown area of the Lakeview neighborhood and the gay- and lesbian-friendly area in the Andersonville neighborhood. These North Side pockets are full of nightlife, including bars that cater to the lesbian and gay community. If you walk around either Halsted or Broadway streets, you'll be sure to find a bar that fits your bill for the evening.
The Closet, located on Broadway in Chicago's Boystown, is a bar that is open to everyone, gay or straight. However, it is predominantly known as a lesbian bar, as it was opened by two lesbians in 1978. The bar is small and known to be a dive, but it it packs a lot of entertainment. One of a handful of bars that still operates with a 4 a.m. liquor license — 5 a.m. on Saturdays — it is also a great late-night spot for when all the 2 a.m. bars in the area close. Want to show off your singing expertise? The Closet hosts karaoke on Thursday nights. Remember to bring cash, though, as this bar doesn't take plastic.
The Kit Kat Lounge & Supper Club is located on North Halsted Street in Chicago's Boystown. Kit Kat is a trendy place to dine and drink — the martinis are acclaimed citywide — and is welcoming to all people, lesbian, gay or straight. If you're out for a night with the girls, you'll enjoy the drag show at Kit Kat; it happens every 20 minutes from 7 p.m. to midnight. There is no stage, so the performers interact among the tables, sometimes inviting guests to participate.
Big Chicks is located in Chicago's Andersonville neighborhood. This neighborhood is mostly known for its Swedish heritage, but it is also known as the most lesbian-friendly area of Chicago. In that vein, Big Chicks is also mostly known as a lesbian bar, but it is welcoming to people whether they are gay or straight. The bar offers free a buffet on Sunday, and it has free Wi-Fi if you're looking for a place to work while you enjoy a beer and a burger.
Berlin is located in Chicago's Lakeview neighborhood, just west of what is considered Boystown. This 4 a.m. bar is more of a dance club than it is a place to sit and chat with your friends, and that's how the patrons of Berlin like it. On the first Sunday of every month, let out your inner Material Girl at Berlin's Madonnarama. Don't worry about getting home, either, because Berlin is located practically underneath the CTA's Brown and Red Line stop at Belmont.