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Dorothy

Dorothy

2500 W Chicago Avenue, Lower Level, Chicago, IL 60622

Look for the unmarked red door on Chicago Avenue and head downstairs into Dorothy, a wonderfully atmospheric lesbian cocktail lounge inspired by the 1970s. Rich colours, plush seating and subdued lighting give this welcoming West Town hideaway a distinctly retro feel, making it a brilliant choice for a date or a relaxed evening with friends.

Dorothy puts queer women at the heart of its community while welcoming the wider LGBTQ+ crowd. Its changing calendar includes DJs, live music, karaoke, film nights and social gatherings, so there's often more happening than just cocktails. It's intimate, full of personality and one of Chicago's most distinctive LGBTQ+ venues.

Lesbian, Cocktails, Cosy

Good for:

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Popular Bars in Chicago

Granville Anvil

Granville Anvil

The Granville Anvil is a dimly lit and manly bar that draws a small community crowd particularly on weekends. There are no frills, just a good old fashioned gay pub with faded basement vibes that appeals to those who want a simple beer with down to earth people and none of the fuss that you might find elsewhere on the gay scene.
Big Chicks

Big Chicks

Colourful, friendly and gloriously unpretentious, Big Chicks is one of those Chicago LGBTQ+ bars that feels like a proper neighbourhood institution. Its walls are packed with art, the drinks are reasonably priced and the crowd spans different ages, genders and identities, creating a welcoming atmosphere that keeps regulars coming back. The food is another big attraction, with generous American comfort dishes making this an excellent choice for combining dinner with drinks. Weekends bring a livelier atmosphere with DJs and dancing, while quieter evenings are perfect for catching up with friends or getting to know the locals. It's refreshingly different from the glitzier Northalsted clubs and well worth the trip to Uptown. Just remember to bring cash, as cards aren't accepted.
Atmosphere

Atmosphere

If you like your gay bars with a little more attitude and a few handsome distractions, Atmosphere is a Chicago favourite. This lively Andersonville venue combines the easy-going feel of a neighbourhood bar with neon lighting, go-go dancers and a soundtrack that gets considerably more energetic as the evening progresses. It's a fun alternative to the bigger Northalsted clubs, attracting a friendly mix of locals and visitors who come for the drinks, music and entertainment. Expect DJs, themed parties, drag and regular special events, with male dancers providing an additional reason to linger. Whether you're starting your evening or settling in for a late one, Atmosphere delivers plenty of personality without taking itself too seriously.
The Closet

The Closet

A staple video bar in the Boystown community, The Closet walls have been a second home to many since 1978. The Closet is a great place to kick back with friends or meet new people, whether you're looking to relax after work, or kick start your night. The Closet attracts a mostly lesbian crowd who pack the small bar and create a super friendly atmosphere, so all identities are welcome for dancing, games, and karaoke.
Jeffery Pub

Jeffery Pub

Jeffery Pub is a classic south-side institution that caters to a mixed crowd. Pitchers of brightly coloured cocktails along with lively music from a range of genres make a vibrant and fun space for parties or getting together with friends for a night out. The atmosphere is always welcoming thanks to friendly patrons and staff, so people keep coming back for great value happy hours and nights of dancing.
Sidetrack

Sidetrack

No visit to Chicago's gay scene feels quite complete without a stop at Sidetrack. One of the biggest and best-loved LGBTQ+ bars in the city, this sprawling Northalsted institution has something for almost everyone, from its famously strong frozen cocktails to enormous video screens, multiple bars and a fantastic rooftop deck. Sidetrack attracts a wonderfully mixed crowd, including plenty of bears and their admirers, and its different spaces make it equally enjoyable for a relaxed afternoon drink or a big night out. The legendary show-tune singalongs are a Chicago tradition, while themed pop parties, drag performances and weekend dancing keep the energy high. On sunny days, head straight for the rooftop and enjoy some of the best people-watching in the neighbourhood.

Tours & Experiences in Chicago

Chicago does big-city drama particularly well. Cruise the Chicago River for some of America’s best architecture, visit Millennium Park and the Art Institute, then head into one of the city’s neighbourhoods for food, drinks and a little more local flavour after dark.


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