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About Chicago
Chicago is the nation’s third largest city and boasts a large and vibrant gay community. Like New York or Atlanta in their regions, Chicago serves as the Midwest’s cosmopolitan hub and attracts young and old alike- all looking to escape to the big city.
Gay life (and gay bars) in Chicago is mostly concentrated in two areas: Boystown (really "East Lakeview") and Andersonville which is farther up the city’s north side. Bars and clubs have one of two licenses: most close at 2am (3am on Saturdays) and a few stay open after-hours until 4am (5am on Saturdays). If you’re up for a late night, you’ll find the after-hours bars packed after the other bars close.
Chicago Hotels
Hyatt Regency Chicago
Gay friendly, mainstream hotel in the heart of the windy city. The hotel is ideally situated within the Magnificent Mile. An American version of the Champs-Elysées. Try Stetsons Chop House, top rated steakhouse with live entertainment.
151 East Wacker DriveChicago
Tel No: +1 312 565 1234
Hilton Chicago
Rock-solid gay friendly Hilton offering. Great location on Michigan Avenue overlooking Grant Park and Lake Michigan. 1543 guest rooms and 3 restaurants. All you’d expect is here – a reliable option.
720 South Michigan AvenueTel No: +1 312-922-4400
InterContinental Chicago
Historic building (originally opened in 1929) in a good location. Good showing from this upmarket chain. Great views add to the appeal. Popular business traveller option.
505 North Michigan AveTel No: +1 888-444-0401
Sofitel Water Tower
Striking dramatic downtown building. Outstanding views throughout the hotel. Cool inside too – a genuine full-luxury/design balance. Expensive but far from crazy.
20 East Chestnut StreetTel No: +1 877-813-7700
Hotel Monaco Chicago
A far-from-stuffy business-oriented Kimpton Hotels offering. Art Deco kitsch inside- and it works well. Perfect central location for anything else. Expect to pay a little more for this gay friendly establishment.
225 N Wabash AveTel No: +1 312-960-8500
Fairmont Chicago
Stylish and modern hotelwith great views of the lake and the city. Good business-friendly downtown location. Occasional chance of celebs when they’re in town. An expensive classy offering from this upmarket chain.
200 N Columbus DrTel No: +1 312-565-8000
Chicago Bars / Club
Sidetrack
Sidetrack is Chicago’s premier Video Bar.Catering to the Gay and Lesbian community.Playing today’s hottest hits.SunFri 3pm2am Sat 3pm3am.
3349 N Halsted StChicago
Tel No: +1 773-477-9189
Atmosphere
Atmosphere attracts and welcomes a mixed but mainly gay and lesbian crowd.Stylish and comfortable bar area and a good selection of beers on offer.Dance floor with DJs playing house and dance hits.The male dancers performances are the most popular nights .
5355 N. Clark StChicago
Tel No: +1 773 784 1100
Baton Show Lounge
A Chicago tradition…it’s been around for over 40 years! Catch some of the world famous drag shows. Shows Weds – Sun. Reservations are recommended.
436 N. Clark St.Chicago
Tel No: +1 312 644 5269
Hydrate
If you like dance/techno you will love it.Mostly male younger crowd.One of the best gay clubs in Chicago.Best time to be there is 1230-3:30.
3458 N. Halsted St.Chicago
Tel No: +1 773 975 9244
Crew Bar & Grill
Crew is a state of the art sports-themed gay bar and grill.Offers good beers tasty food and a 92 inch screen and multiple monitors.65 beers on tap and in bottle plus appetizers sandwiches salads and desserts.Check out their website for party nights.
4804 N BroadwayChicago
Tel No: +1 773 784 2739
Little Jim’s
Little Jim’s was established 1975.Famous for having been one of Chicago’s first ever gay bars.Its location on N Halsted helped to begin the creation of the area now known as Boystown.A popular drinking place especially when other gay clubs bars have closed.
3501 N Halsted StChicago
Tel No: +1 773 871 6116
Chicago Restaurants
Yoshi’s Cafe
Yoshi’s is a great place right in the heart of Boystown. Asian/French fusion with some interesting variations of American cuisine. Yoshi’s Cafe is gay friendly and a great place to bring a date. Open til 10.30pm and closed on Mondays.
3257 N. HalstedChicago
Tel No: +1 773 248 6160
Morton’s The Steakhouse
Hugely-popular steakhouse. One of three in the city. Feels like an exclusive dining club. Expect to pay a bit more for the high quality food.
1050 N State StTel No: +1 312-266-4820
Tiffin
Upmarket Indian restaurant in the Warren Park area. Boasts an authentic and wide-ranging menu. Friendly pleasant ambience. Far from expensive.
2536 W Devon AveTel No: +1 773-338-2143
Red Light
Trendy Asian restaurant in a good location. Much more modern than traditional fare. Draws a young-ish and trendy crowd. Not too expensive though.
820 W Randolph StTel No: +1 312-733-8880
Angelina Ristorante
This intimate and cozy Italian restaurant serves delicious classic Italian recipes.The wine list is available by the glass at reasonable rates.Dishes are prepared to perfection at this gay friendly restaurant.Perfectly located on the edge of Boystown.
3561 N Broadway St.Chicago
Tel No: +1 773 935 5933
Shaw’s Crab House & Oyster Bar
Featuring two distinct dining options the casual oyster bar and the more formal main dining room. Huge range of seafood dishes. Popular venue – make sure to book in advance. Classy without any pretentiousness.
21 E Hubbard StTel No: +1 312-527-2722
Chicago Arts, Culture and Leisure
The Underground Wonder Bar
A Chicago classic coming up for twenty years old. Live music venue that’s open 365 days a year. Jazz and blues dominate as you’d expect. Small intimate informal and fun.
10 E Walton StTel No: +1 312-266-7459
Wrigley Field
The Chicago Cubs’ famous stadium. Tours available on scheduled days running from 9.30am to 4.30pm. Home games throughout the season. A must-see for any genuine baseball fan.
1060 W Addison St # 1Tel No: +1 773-404-2827
Sears Tower
Chicago’s most dominant structure at 1454 ft high. Outstanding views into Indiana Michigan and Wisconsin from the 103rd floor skydeck. A ‘must/should do’ if you’ve daytime to spare in Chicago. Quite inexpensive.
233 S Wacker DrTel No: +1 312-474-0090
Zanies Comedy Clubs Inc
Comedy club in the north of the city. Small but popular club – been going for 30 years. Shows 7 nights a week. Far from expensive.
1548 N Wells StTel No: +1 312-337-4027
Chicago Gay Pride 2010
Held every year in Chicago. June Pride Month features dozens of social cultural athletic and political events. The Annual Pride Parade is held in East Lakeview on 27th June. Check the website for more information.
ChicagoTel No: +1 773 348 8243
Hollywood Beach
Hollywood Beach is a popular beach for all Chicagoans.Now named Kathy Osterman Beach.The gays and their friends hang out on the south side of the beach.Most popular on Sundays during the summer.
W Hollywood Ave & Lake Shore DriveChicago IL
Chicago Adult Entertainment
Bijou Theatre
Bijou World is a gay male sex club club with cruising area.There is a theatre lounge showing porn videos including vintage films.Booths gloryholes a circle jerk room and a dungeon with slings.Open 24×7.
1349 North WellsChicago
Tel No: +1 312 943 5397
Lucky Horse Shoe Lounge
Located in the heart of Boystown.This highly frequented gay bar features male strippers.Performing every night of the week and during the day on weekends.The boys in this darkened bar can be very friendly as they collect their tips.
3169 N Halsted StChicago
Tel No: +1 773 404 3169
Manhandler
Chicago gay cruise bar.Good mix of video porn in front part of bar.Pretty busy bar but nothing special.All the action is outside in the barn area where anything goes and we mean anything.
1948 N. Halsted St.Chicago
Tel No: +1 773 871 3339