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Amanda Boleman
Created byAmanda Boleman

Boystown and Beyond: A LGBT Guide to Chicago

Featured Guide
You'll know you're in Boystown by the rainbow fixtures and flags adorning nearly every street sign and storefront. As the first officially recognized gay village in the nation, this Chicago hood is home to over 30 gay and lesbian restaurants, clubs and bars. If you've already conquered the Boystown circuit, head a little further north to check out the Uptown scene or go south to the theatre and shopping districts for more LGBT-friendly fun. 
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Sidetrack

Show tunes and slushies keep the LGBT crowd coming back to Sidetrack, which many have said is the best gay bar in Chicago, or perhaps, the world! You can't go wrong with the Ketel One Crush--you'll want to try one even during the cold winter months. You can always warm up by dancing around and belting out...

Hotel Allegro Chicago - a Kimpton Hotel

Put on your leopard print bathrobe and unleash your inner sex kitten at the Hotel Allegro Chicago. Seriously, there's leopard print bathrobes in the closet! Awesome. Next, head out in the North Loop neighborhood to check out a show in the theatre district and do some shopping along the Magnificent...

Spin Night Club

Spin is nothing but non-stop fun with contests, events and great drink deals. The entertainers know how to bring the energy up even when there's small crowds. They really get the audience involved and put on awesome performances. You can show your star power every Monday night during the Amateur...

Steamworks Baths

It's important to stay healthy even when you're on the road, both physically and sexually. At this 24/7 gym, sauna and bath house, you can get your fitness on, kick back or just play with other health-conscious, 18+ men and free HIV testing is offered every Tuesday. While it tackles the serious stuff,...

Big Chicks

Known for great service and delicious BBQ, Big Chicks is Uptown's top gay bar. Not only do they offer great deals ($1 burgers on Mondays!), but there's almost always some sort of fun event going on. Locals love the neighborhood feel of the restaurant by day and the dance-until-we're-too drunk vibe by...

Scarlet Bar

Great music makes this Boystown staple a must-hit nightlife spot no matter your sexual orientation. The staff is always energetic and fun, encouraging you to get on the dance floor even when it's not packed. Keep the party going at Scarlet's Sunday Liquid Brunch to down $12 bottles of champagne....

Hydrate

This late-night hot spot will have you feeling anything but hydrated. Get ready to sweat with resident DJs like DJ Phil DaBeatz delivering hot house beats all night long. Don't miss $1 drinks on Tuesdays and the popular Hydrag Revue on Wednesdays.

Kit Kat Club & Supper Lounge

Martini lovers: the Kit Kat Club is the lounge for you. With over 200 cocktail offerings, you'll spend half the time debating which flavor to try. The Samoan Girl Scout and Blue Hawaii are local favorites. Kit Kat is also known to have beautiful drag performers who really know how to entertain a crowd....

Angelina Ristorante

If you want Italian served with a side of man candy, head to Angelina. The $20 Champagne Brunch is served up by a gorgeous wait staff that keep the bottomless mimosas flowing from 11-2:30 on Saturdays and 10-2:30 on Sundays. Get there early to avoid long waits in this intimately small space....

Brown Elephant Resale Store

Owned by the Howard Brown Health Center, one of the largest LGBT organizations in the nation, the Brown Elephant Resale stores (4 locations in the Chicago area) donate their proceeds to provide care for their network of over 18,000 lesbian, gay, bisexual and transexual clients and patients....