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Chicago’s Boystown and Andersonville: 13 LGBTQ hotspots in the world’s top gayborhoods

Party-goers convene at Sidetrack bar’s outdoor patio

Sponsored: Chicago is a welcoming city where you’ll find many gay-friendly events, restaurants, boutiques and more.

But the largest city in Illinois is also home to two proper, bona fide gayborhoods known worldwide: Boystown and Andersonville.

Photo ©Adam Alexander Photography 2016/

Here, you’ll find thriving LGBTQ communities – some of the largest in the States. If you’re looking to immerse yourself in authentic queer US culture, they’ll welcome you with open arms.

Both boast a pioneering spirit: they’re exciting, imaginative and creative, reflecting a modern Americana that is a bit gritty and definitely down to earth. Here’s our pick of the best of both…


Firstly, the most iconic (and iconically-named) gayborhood ever has an energy all its own. It offers fabulous shopping, trendy restaurants, lively bars and energetic dance clubs. Most importantly, it’s a true hub of LGBTQ nightlife, with most of the bar scene found along Halstead Street.

Queer people can enjoy great music and excellent drinks in every venue imaginable, from lively dance floors to outdoor patios. There are also countless diva drag shows, comedy nights, late night DJ sets and show tune brunches to enjoy.

Cell Block

First up we have this fabulously unpolished drinking hole, with free pool on Mondays and Tuesdays and free Wii every night. On the first Friday of every month, all drinks are $4 (£3.15, €3.59).


This pumping, unpretentious nightspot’s been around since 1982. It boasts eight levels hosting up to 1000 people, and one of the gayest soundtracks around. Monday is show tunes night, Tuesday is 90s and early 00s, and so on…

3 Hydrate

Late night license alert! This dynamic dance club is open until 4am every night of the week except for Tuesdays, when it’s closed, and Saturdays, when it’s open until 5am.

4 Scarlet

Now for a bit of vintage charm in this gorgeous, throwback lounge-style bar, its chic interior the result of a refurbishment after a fire in 2009. The name’s inspired by the trend for LGBTQs to wear scarlet-colored clothing as a message to each other in the 1920s.

5 Berlin Night Club

Another vast space offering a raucous nightclubbing experience, and Berlin also parties hard into the not-so-early hours every night. It’s open until 4am Sundays-Fridays, and 5am on Saturdays.

6 Roscoe’s Tavern

Another long-serving institution, Roscoe’s has been serving the LGBTQ community since 1987. This dragtastic drinker will have a live Spice Girls tribute act on 25 July that we would do anything to see! Hai si ja, hold tight!

7 Kit Kat Lounge & Supper Club

Another drag hotspot, this little gem is known for its outrageous brunches hosted by in-house divas and its sleek ‘South Beach meets Hollywood’-inspired decor. Expect 100+ martini options and upscale New American cuisine.

Briar Street Theatre

Bolstering Boystown’s village-feeling, the district also boasts its own 300-seat theater. It’s one of the outposts of the ever-popular performance art troupe Blue Man Group. These three bald, blue-headed men are icons of alternative culture, combining music, comedy and technology to comment on the human experience.

9 Wood

Boystown has no shortage of amazing dining options. Wood, a spot for New American fare, has received rave reviews, and won Michelin Bib Gourmand awards five years running. But you can also find excellent restaurants serving just about any kind of global cuisine here. These include European, Thai, Korean, Mexican, and more.


Secondly, the vibrant, friendly Andersonville is a thriving example of colorful urban living with a plethora of quirky, locally-owned businesses.

Andersonville has some of the best kitschy, offbeat attractions in the city – you won’t see any national chains but you will find an eclectic array of independent boutiques, galleries and theaters. Plus, it has an amazing dining scene.

1 m.henry

An epic brunch spot offering an array of modern American cuisines and healthy dishes. It’s known for its love affair with natural, seasonal, organic, locally-sourced ingredients. Therefore everything on the menu sounds impossibly healthy and delicious. A quick example: the dandelion, shallot, and leek omelette. Yum.

2 Big Jones

Next we have an outpost of the American South in Northern Illinois offering everything from shrimp and grits to cornbread, okra, crawfish and gumbo as well as bourbon, craft beer and frozen cocktails. Expect sustainably-grown heritage and heirloom crops and livestock, plus sustainable seafood.

Hamburger Mary’s

Especially noteworthy is this member of an independently-owned and gay-themed hamburger chain. Yes, you read that correctly. Why not enjoy a delicious burger on the outdoor patio of Mary’s Dining Room, before enjoying a cocktail and cabaret in Mary’s Attic and then a beer in the Andersonville Brewing sports bar and brew pub next door? What’s more, its drag shows are award-winning.

The Guesthouse Hotel

Finally, mix boutique hoteling with a more comfortable home-from-home experience. We’d recommend renting out one of the opulent and luxurious two-or-three bedroom suites, and making it a family (or urban family) affair. Be sure to check out the in-room spa services and also the glamorous roof deck.

Plan your trip at

Illinois Office of Tourism is a client of Gay Star News.