Chicago home to Boystown the oldest LGBTQ neighbourhood in USA.
On the shore of Lake Michigan, Chicago was incorporated as a city in 1837. It grew rapidly in the mid-19th century but the Great Chicago Fire in 1871 destroyed several square miles and left more than 100,000 homeless,
The cities population continued to grow to 503,000 by 1880 and then doubled to more than a million within the decade.
Gay, lesbian, transgender, queer or bisexual, however you identify, you’ll feel right at home in Chicago.
Boystown, officially known as Northalsted, is the oldest LGBTQ neighbourhood in the country.
The area’s proud history is on display with the Legacy Walk, which commemorates notable LGBTQ heroes and historic events. The walk is a great way to tour this neighbourhood.
Chicago is a major transportation hub in the United States. Seven mainline and four auxiliary interstate highways run through Chicago and its suburbs. Segments that link to the city centre all named after influential politicians.
The buses and trains of the CTA (Chicago Transit Authority) are a fast and cost-effective way to get into and around the city. Known as the "L" (though they may be elevated or underground) the trains are a fun way to see the city.
The Chicago Transit Authority is open 24/7 and the Blue Line will take you all the way from the airport to the centre of town. This is one of the cheapest ways to get you to your destination.
The Blue Line ‘L’ train will take you from airport to downtown in about 45 minutes. You can get the Blue Line from Terminals 1, 2, and 3 easily by just following the signs posted at the airport that say “CTA Trains” or “Trains to the City.”
GO Airport Shuttle
This is one of the most popular shuttle services from Chicago airports to the city centre if you want direct transportation to most downtown hotels. Customers are allowed 1 standard-sized suitcase and carry-on, but anything extra may require a private van. Operating 24 hrs/day taking 45-60 minutes.
Places to stay
Named for the elevated railway loop that circles the city the Loop is the most central downtown neighbourhood of Chicago and the most obvious choice for many thinking about where to stay in Chicago.
If you’re interested in a hip and trendy experience during your stay in Chicago, then consider staying on the Near North Side.
Lakeview is a fantastic choice for your stay in Chicago and home to Boystown the LGBTQ neighbourhood. Just north of Lincoln Park, it’s known to be safe, quiet, and relatively peaceful, with boutique hotel options.
Bars, Cafes, Clubs & Parties
With Chicago being one the third biggest city in the USA you would expect an incredible gay nightlife scene which luckily, the windy city delivers.
Depending on your mood, you can have lots of choice. Anything, from relaxed upscale cocktail bars to an all-night dance parties. There are also plenty of cruise\dive bars, sexy go-go boys, fabulous drag shows and other fun events to cater to every taste!
The LGBTQ neighbourhoods in Chicago is mostly concentrated in two areas: Northalsted (really "East Lakeview") and Andersonville, which is on the city's north side.
The bars and clubs have two type of licenses: most close at 2 am (3 am on Saturdays) and a few stay open after-hours until 4 am (5 am on Saturdays). So if you're up for a late night, you'll find the after-hours bars packed after the other bars close.
Progress Bar is a hip nightclub with craft beer, fabulous DJs, upscale vibes and cute bartenders. Join your queer friends for designer cocktails and late-night dancing under the overhead sculptured installation consisting of 19,000 glimmering light bulbs.
SideTrack is large bar with a unique mix of music videos, multiple bar spaces, rooftop deck open year-round. SideTrack is considered one of the best gay nightlife spots not only in Chicago but in the entire country.
The Lucky Horseshoe Lounge features hot male dancers 7 days a week, 365 days a year since 1989. Gay male strip clubs are quite rare in US so you know the Lucky Horseshoe Lounge has to be doing something right to be around since 1989.
Scarlet Bar is a drink and dance venue with wonderful daily happy hour drink specials in a vintage-inspired gay bar. Generally a busy popular drinking bar with a late-night lounge vibe and boozy Sunday brunch.
NorthEnd is Chicago’s neighbourhood gay sports bar since 1983! Offering cold drinks, a great beer selection, pool, darts, and all the games on TV. With a low-key vibe a tempting place to chill out with cheap drinks, friendly flowing conversation and occasional karaoke.
Charlies is a ‘traditional’ gay club frequented by cowboys. Dance music, line dancing and drag shows brings the crowds keep flowing in.
Hydrate is one of several premiere spots for drag shows, music, dancing, and late-night parties. Combining Chicago’s hottest male dancers with some the best female impersonators. The Sunday Funday is a post-brunch party featuring go-go dancers. A late night venue open nightly till 4 am and 5 am on Saturdays.
The Closet is a video bar that open since 1978. A chilled place very down-to-earth bar, welcoming everyone for dancing, games & karaoke later at night, or drag shows occasionally.
Kit Kat Lounge & Supper Club is a the place to go for drag-queen divas who perform nightly at this upscale venue. With a huge cocktail list of more than 200 drinks to choose. Shows run every 20 minutes, starting at 6.30pm through midnight, or 1 am on weekends, and a Divalicious Brunch on Sundays.
Splash is a modern beautiful decorated gay bar serving strong drinks, with a friendly-but-cool vibes.
Bobby Love’s is a quieter gay bar popular with older guys whom just prefer quiet conversations and classic hits from the jukebox. Nothing trendy here which is just the way the locals like it.
Roscoe’s Tavern is a cute and popular gay bar that has been drawing in the local LGBTQ crowd for over 30 years with a fun dance floor, friendly service, a long sociable bar, and fun outdoor seating.
Fantasy Night Club is the biggest gay nightclubs in Boystown. Considered a bit overpriced
Davenport’s Piano Bar and Cabaret offers great performances, excellent drinks and singing staff. With an intimate vibe with frequent sing-alongs, open mike and karaoke nights.
Big Chicks is a friendly and inclusive LGBTQ-focused watering hole in Up Town. Supporting LGBTQ sports teams and welcoming everyone across the rainbow community (and allies). This colourful bar has been an institution in Chicago’s LGBTQ and Uptown communities for decades and has been inducted into the Chicago LGBTQ Hall of Fame.
Touche is an infamous gay cruise bar in Chicago is catering to the leather crowd since 1977. Offering draft brews, darts, affordable prices and lots of kinky events to draw in like-minded crowds.
Cell Block is a notorious bear/ leather bar with billiards, darts, and drink specials. The atmosphere ranges from quiet to extremely raucous, depending on the day and time you visit. Cell Block has a cash-only policy.
Officially known as Kathy Osterman Beach but with a nick name of Hollywood Beach, is one of gay Chicago’s best-kept secrets. There is no carpark here, so public transport is your best option, but the pure white sand and gorgeous bodies will instantly have you dreaming of Hawaii or Cancun over Illinois.
Down-to-earth with a friendly crowd, this is the go-to spot for gay men to flock to sunny days.
Wood is a magnificently pretentious gay restaurant. Stylish surroundings, craft cocktails, a New American menu, and a walk-up Frites window. The staff are hot, competent and sassy.
Even though Chicago has a diverse LGBTQ community and is a very popular gay vacation destination there is only one sauna.
Steamworks Chicago is a private men’s bathhouse for men 18+ years and older. Open 24/7, every day of the year. There are play areas spread across three floors, including the infamous “Windy City Blowholes” 6-sided glory hole booths, multiple TVs and private booth play areas, suck ramps, a public sling, and a voyeuristic viewing area.
There is also a full state-of-the-art gym, with a wet area that has multi-man whirlpool, showers, eucalyptus steam room and two separate dry saunas.
Andersonville which is known for the deep Swedish roots, array of eclectic independent businesses, and their welcoming, diverse LGBTQ community and therefore generally good shopping neighbourhood.
Main LGBT Events
In May the International Mr. Leather and Mr. Bootblack is award during a kinky weekend as well as the popular Victory Party & Black and Blue Ball.
In June, you’ll find Boystown is the heart of the city’s annual Pride Month celebrations, which include two days of LGBTQ+ pride, music, and drag shows at Chicago Pride Fest, and culminates with the famed Chicago Pride Parade held typically at the last Sunday of June.
There is in addition in June the Chicago’s Dyke March which is a grassroots celebration of dyke, queer, bisexual, transgender, and lesbian resilience.
Boystown’s Northalsted market days weekend is held in August . This weekend-long party celebrates LGBTQ identity with all-day live music, unique vendors, arts and crafts, food & drink, DJs, and dancing at the largest street festival in the Midwest.
The Reeling Film Festival is held in September and showcases LGBTQ+ films and filmmakers, with a goal to counteract any misrepresentation and stereotyping of LGBTQ community in the mainstream media. This is one of the longest running film festival of its kind in the world.
The Northalsted Halloween On Halsted Parade take place in October which is a crazy parade held in the Boystown Gay area and features thousands of people vying for best dressed prices with a panel of gay celebrity judges.
Currency – United States Dollar (USD)
Language – English
Visas – Most visitors from Europe do not need a visa. ESTA permits citizens of 40 countries to enter the US without a visa.
Best Time To Visit – March - November
Timezone – Varies per state. Check per destination.
Homosexual Activity – Legal but attitudes vary per state
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