NOTE: This is an archive article. For an updated and expanded Chicago article click DailyXtraTravel
The country's third-largest city, Chicago has a vibe totally different
from its competitors on either coast. Nicknamed "Paris on the Prairie"
because of its wide boulevards and tree-shaded parks, Chicago has a lot
in common with that European capital. It has world-class museums, a
breathtaking array of restaurants and gay nightlife that rivals any of
This sophisticated city was home to the world's first
skyscraper. (That was 1885, and the Home Insurance Building was just
nine stories tall.) Since then, the city has attracted famous
architects like Louis Sullivan and Mies van der Rohe. The skyline's
main feature these days is the iconic Willis Tower, the former Sears
Tower, which is slated for a new silver paint job.
From O'Hare International Airport, take
the Chicago Transit
Blue Line train heading east. For
Transitchicago.com. A taxi to Lakeview
The Windy City is a breeze to get around, and a car is just not
necessary. Many train and bus lines operate around the clock. Bus
numbers 22 Clark and 36 Broadway and the Red Line EL will get you most
anywhere in gay Chicago. Visit TransitChicago.com or
DriveLessLiveMore.com to plan your route. A Chicago Transit
visitor's pass is available for one to
Boystown: Chicago's biggest concentration of gays is in the high-
energy neighborhood of East Lake-view, perhaps better known as
Boystown. It's a triangle between Belmont Avenue, Halsted Street and
Andersonville: The mellower Anderson district stretches into
Gay & alternative media
Magazine, Chicago Free
Press and Windy City
Times are the
city's gay news sources. Boi
Magazine is a glossy bar mag with good area bar listings, map and events calendar. The Chicago
Reader is a great alternative
Chicago Pride Fest, with live music on two stages, food vendors, arts
and crafts, takes place in June.
The Center on
Halsted (3656 N Halsted) is one of the world's best gay
community centers -- and its construction was financed without any
The Magnificent Mile is a high-end shopping district on Michigan Avenue
between the Chicago River and Oak Street. The Bucktown and Wicker Park
neighborhoods, both off North Milwaukee Avenue, are full of boutiques,
galleries, theaters, eateries and nightclubs.
'Just be whoever you want'
Nightlife options can often seem limited for gay men who would rather
dance to Le Tigre than Lady Gaga or who want to bring along a lesbian
friend or two. But thanks to the efforts of several party people, the
Windy City now has a lot to offer those in search of something a little
"I feel like many bars on Halsted can be very unwelcoming to
people that are a little different, whether that means you dress
differently, you're a woman or a trans person," says Erik Roldan, a DJ
of both the dancefloor and radio waves. "You end up seeing the same
types of people, who are surprisingly conservative in a lot of ways."
Roldan, also known as Stinky Pinky, spins Fridays at Wang's,
3317 North Broadway, a low-key, dimly lit spot decked out in Asian
decor. The bar offers the perfect opportunity for enjoying a marvelous
martini -- try the green tea variety -- and music that skews indie.
If you're hungry for dancing, Berlin Nightclub, 954 West Berlin,
is where you need to be. The club is open until the wee hours of the
morning and caters to artsy and punk types while offering a hodgepodge
of themes. A quarterly Bjork night, a monthly Madonnarama party, and
the latest addition -- a monthly Perv night, complete with lots of
onstage spanking -- highlight the diverse party lineup.
"The music at Berlin is accessible yet different, and we don't
want to alienate anyone," says Chester Holowicki, who DJs on Thursdays
at the club. "It's the spot where you can be whoever and whatever you
And that even includes you Gaga monsters out there: both
Holowicki and Roldan were quick to admit they couldn't resist an
occasional pop gem. But expect your Gaga served up in a mix with indie
queens located a bit left of the mainstream, like Goldfrapp or Peaches,
as well as fathers of new wave, like New Order or Yaz.
"I definitely will play some pop music, but there's always some
much more interesting and newer stuff happening in the underground that
might become pop later," Roldan says. "I like to try pushing you to
listen to and like something you may not have heard before."
"We're gays and we're supposed to be smart. So let's challenge
ourselves and embrace something different," Holowicki says.
Small town, big backyard
In Too Much Light Makes the Baby Go
Blind, the Neo-Futurists zip
through 30 original plays in 60 minutes.
Never the same show twice, the
lightening-fast performances are
hilarious and sometimes heartbreaking.
Even though the show has been running
for 20 years, it's sometimes hard
to get a seat at the renowned theater
troupe's home base, the
Neo-Futurarium (5153 N. Ashland Ave. 2nd Fl).
The improv group brings fans of
alternative theater to
Andersonville, one of Chicago's most
popular north side neighborhoods.
Located roughly five miles from
downtown, this enclave is known for
being a bit offbeat.
That's clear from the
neighborhood's other theater and musical
troupes, which present everything from a
live-action gay soap opera to
a tribute to The Carpenters. There's
also a bi-monthly queer music
showcase called Homolatte.
Art for art's sake: The Art Institute of
Chicago (111 S Michigan) is a
world-class museum and school of art and
design. There's free admission
Thursday and Friday nights.
Museum pieces: The Leather Archives
and Museum (6418 N
Greenview), open Thursday to Sunday, is
a must-see shrine to leather
Bird's eye view: The Willis
Tower (233 S Wacker Dr),
Chicago's tallest building, (formerly the Sears) has great views. A drink at the bar on the 95th floor
has similar views to the observation
deck, and costs less.
Going parking: Millennium
Park (55 N Michigan) is an
eye-catching urban park where you'll
find plenty of men there for the
A night at the theater: Steppenwolf Theatre
Company (1650 N Halsted) a
crucible of talent, is where John
Malkovich made it big.
City Pass Chicago gets you into five attractions for $69.
Chicago Water Taxi takes you between Chinatown and Michigan Avenue for
Download Chicago Tours has free tours you can download in five
Go Chicago offers discount cards that can save on sightseeing costs.
Hot Tix offers last minute half-price theater tickets.
World's hottest leather competition.
Memorial Day Weekend, May 28-31, 2010
Gay-friendly festival held in mid-summer
('midsommar' in Swedish).
Chicago Pride Fest,
with a Lakeview Parade
Sunday June 27, 2010,
and a month of events all over metro Chicago.
The Midwest's largest outdoor street
festival, with big gay crowds.
August 7-8, 2010
Aids Run &
Popular annual fundraising event
October 2, 2010
Chicago Lesbian and Gay International
November 4-13, 2010
Chicago (20 W Kinzie; 312-
395-9095) downtown location,
Hawthorne Terrace (3434 N
Boystown location, free breakfast,
Suites Hotel (933 W Belmont;
773-404-3400) art deco-style
building, Boystown location, at Belmont
Inn and Suites Downtown (15 E
Ohio; 312-894-0900) affordable
rates, super clean, Downtown location,
State; 312-202-6000) modern boutique
hotel, big windows overlooking State
Chicago (720 S Michigan;
312-922-4400) over 1,500 rooms,
host to International Mr Leather
Chicago (225 N
Wabash; 866-610-0081) downtown
boutique hotel, luxurious French decor,
part of Kimpton chain.
Hotel (528 W Brompton; 773-404-
3499) cozy rooms,
closest to the lake in Lakeview.
House (1248 W Ardmore; 773-728-
5414) gay B&B, between lake
and North Clark nightlife.
Arms Guest House (6408 N
312-498-9979) North Side
location, five rooms with
Toscana Guest House (3447 N
Halsted; 773-404-2643) gay-friendly
lodgings in Boystown.
(24 E Congress Pkwy; 312-360-
0300) downtown location, all
ages, no curfew, inexpensive dorm
House International Hostel &
Hotel (616 W Arlington Pl;
membership, inexpensive dorm beds and
private rooms, just south of
Bars & clubs: Lakeview area
(3160 N Clark) small neighborhood bar with open mic nights, local and celebrity guest drag performances, plus cabaret shows in their piano lounge.
(954 W Belmont) acclaimed multicultural
alternative and queer dance
club, with late-night crowd, performance artists, live music, comedy, drag shows, guest DJs and dancing until 4 or 5am. Just-released cutting-edge nuggets mix easily with the classics here in the hands Chicago's freshest generation of DJ talent.
Love's (3729 N Halsted) tiny
neighborhood bar where karaoke
(3439 N Halsted) casual and relaxed neighborhood saloon with sports on the tube, garden patio bar, jukebox, darts and pool table with picture-window views of the comings and goings on the Northalsted strip. A genuinely friendly staff and decent drinks prices too.
Block (3702 N Halsted) Levi-
leather men's video dance bar with strict dress code enforced in the dark and cruisy rear bar. Catch the Mr. International Rubber events the weekend of November 5-7.
(3726 N Broadway) rollicking country-western bar that morphs into a high-energy dance club after 2am Thursdays through Sundays (until 5am on Saturdays) when other Boystown bars have to close.
(3641 N Halsted) big dance floor,
with Latin nights Thursdays and Sundays, Girls Night Out Fridays, Hip Hop Urbano Saturdays, and other theme nights. Miss Foozie hosts amateur drag Wiggin' Out Saturday cash prize contests in the Rehab Lounge.
(3359 N Halsted) intimate lounge with great window on Halsted, vibrant music from hottest DJs around,
sexy stripper boys on Tuesdays and Thursdays.
(3458 N Halsted) crushingly packed and cruisy dance club with young, fashionable, attractive crowd and staff, hot dancers and contests, blackout parties, drag shows, cabaret and imaginative theme nights like lube wrestling each first Friday. Mondays feature $1 drinks.
Jim's (3501 N Halsted) early or
late-nights for after all the others have closed men's drinking and cruising bar, with cheap drinks.
Horseshoe Lounge (3169 N
Halsted) is a popular bar with Chicago's only every night rotation of erotic male dancers on stage, on the bars and circulating throughout the crowd. Holidays here are always celebrated in style and porn stars in town usually put in an appearance at the Horseshoe.
(1948 N Halsted) men's cruise bar halfway from Boystown to Downtown with very active patio and backroom, especially in the later hours.
(3341 N Halsted) long narrow lounge and cafe for style-conscious metrosexuals.
End (3733 N Halsted) Chicago's original gay sports bar and neighborhood tavern with sports video and TV games, pool tables, dart boards, and an athletic crowd. Bar-sponsored football, water polo, darts, bowling, softball, and volleyball teams hang here, and porn stars headline special events.
(3356 N Halsted) very popular bar complex at Boystown center with compact, intensely active dance area, lounge and pub areas, plus patio and sidewalk food service. A constant stream of events include Wet Boxer Shorts contests, weekly drag contests, and Male Call game nights with Miss Foozie.
(3320 N Halsted) rich decor, small but pleasant escape from the Boystown crush. Rotating events include local artists, independent film, top name DJs, comedy and theme parties.
(3349 N Halsted) spacious video bar compex of many rooms and ambiences, inside and out. At the central big-screen video bar, laugh and sing with the crowd to queer and eclectic fare from their amazing archives. Show tunes are Sunday and Monday favorites and Thursdays are for comedy. Lots of special events, and the biggest, most diverse crowd in gay Chicago. Valet parking available.
(800 W Belmont) energetic young crowd dance club and lounge famous for their Friday night shower contests. Standard amateur boy events now joined by girls, couples, bears and go-go pros on special nights.
Bars & clubs: Northside to Westside
(5355 N Clark) dance bar with strippers
Thursday to Sunday.
Chicks (5024 N Sheridan) local
bar and restaurant for all, patio,
Sunday BBQ buffet. Bear Den at Big Chicks every Thursday night.
The Call (1547 W Bryn Mawr) video, dance and party bar until 2am every night, with pop and retro music and home-inspired entertainment. Easy to reach at the Bryn Mawr Red Line station.
Bar and Grill (4804 N Broadway)
popular music and sports video bar with cute and trendy crowd. Good basic food and 68 kinds of beer inside, or at the sidewalk cafe daily until midnight; weekend brunch 11am to 3pm.
Piano Bar (1383 N Milwaukee,
Wicker Park) mostly straight but gay-friendly piano and cabaret bar with student discounts.
Anvil (1137 W Granville) men's
dive bar, opens early at 9am
for the dedicated regulars.
Hopleaf (5148 N. Clark St) bar with kitchen,
known for their Belgian ale selection.
Spirits (5420 N. Clark St) a wine bar with mostly straight but diverse and gay-friendly crowd.
(6406 N Clark) diverse crowd upper bar includes gay men and women with dance floor, and patio. Downstairs the basement is the Levi-leather/fetish and sex-charged Hole. Also bear events, strippers, and theme parties here. Open late until 4am nightly, 5am Saturdays.
De Vine (1744 Balmoral) wine
bar for an arts crowd, mostly women.
Marty's (1511 W Balmoral Ave) often crowded chic gay martini bar with back patio to relieve the crush. Pineapple-Upside-Down, Strawberry, Pomegranate, and Chocolate Mint are but a few of the martini offerings.
(1829 W Montrose) neighborhood bar in Ravenswood area just off the Montrose (Brown) CTA stop, busiest after 5pm. Mostly gay but welcomes all.
Bar (4923 N Clark) mixed gay
and lesbian neighborhood bar with pool table, large dog-friendly patio.
(5419 N Clark) small dance
bar with outdoor garden, draws
women and transgendered people. Rumored to be closing so call ahead.
(6412 N Clark) leather/rubber/fetish
men's bar with cheap beer, fun contests and porn star events, dress-code and very active and cruisy back rooms.
Pug (4810 N Broadway) neighborhood locals' hangout with comfy
sofas, dance floor, big selection of beers on tap, game shows and acoustic music events.
Bars & clubs: Downtown & Southside
Show Lounge (436 N Clark)
first-rate drag shows for a mostly
Chesterfield (1800 W Pershing) recently tranformed into el nuevo Chesterfield, mixed gender and orientations dance club with a Latin pulse.
Club Escape (1530 E 75th St) Southside dance club with live shows, drag, and retro music draws a slightly older crowd.
(5758 W 65th) sociable neighborhood video bar in the Southwest, near Midway
Airport, with free parking and Chicago Beef dancers on Fridays.
(7041 S Jeffery) video bar with dancing to a South Side groove.
Bar (157 E Ohio) the last downtown gay bar in area convenient to Magnificent Mile shoppers.
Bars & clubs: Suburbs
(13126 Western Ave, Blue Island) mostly gay crowd in southern suburbs with Hot-n-Hunky male dancers hosted by Sarabia, plus karaoke, bear nights and other parties.
(1932 E Higgins, Elk Grove) suburban
dance club, mostly
guys, 'Hunks' show each Thursday.
Velvet Rope (728 W Lake St, Oak Park) new tapas and regular American restaurant and video lounge for mixed crowd in the western suburbs.
Saunas & sex
Video (4923 N Clark) adult gay
video store with screening rooms and accessories.
Theater (1349 Wells) multi-
level porn heaven with large
screens and action-filled garden.
Country (5017 N Clark) grand
old-style bathhouse with all the steamy amenities and lots of male interaction. Famous for their Friday and Saturday midnight nude stripper and guest porn star shows at no extra charge.
Bookstore (3511 N Halsted)
adult magazines and DVDs, video booths
with 'ventilation' -also with Thursday through Saturday late night dance and play floor, with music DJs and light show, 3-7am
(3246 N Halsted) ultra modern gay gym and sauna with all the bathhouse, video, internet and playspace facilities and then some, including live DJs.
For a more complete list of area restaurants click
Sather Restaurant (909 W
Belmont) grand Swedish diner serving
superb breakfast varieties of Eggs Benedicts, omelettes, wraps, pancakes and waffles; also lunch
and justly famous cinnamon rolls. Additional locations in Andersonville, Southport areas and on Broadway (see website).
Diner (3411 N Halsted) award-winning, mostly vegan meat-free meals, brunch, bakery, organic wines and beer, juice bar, margaritas and shakes.
Bar & Grill (3441 N Halsted)
gay crowd for brunch, dinner, beer and cocktails, large outdoor beer garden, music video jukebox.
Bistro (3201 N Halsted)
American contemporary bistro, healthy global cuisine, open seven nights for dinner and for live DJ Sunday brunch with Mimosas and Bloody Mary specials.
Restaurant (3233 N Broadway)
casual vibe, big menu,
always open, all-American diner with breakfast all the time.
Tree (3334 N Halsted) casual American no-nonsense wholesome food Boystown
restaurant, open 7am to midnight, and 24 hours on weekends. Before or after the bars meeting place, quiet afternoon meal, or hearty Sunday brunch.
Orange (3231 N Clark) inventive breakfast, brunch & sandwich fare until 3pm every day. Orange flavored infused coffee a specialty here.
Hole (737 W Roscoe) convenient and tasty late-night slices after
surrounding Boystown bars close.
Diner (3042 N Broadway) good American no-frills diner food includes soup, salads, sandwiches, milk shakes and plenty more from a big menu, 7am to 10pm.
(3640 N Halsted)
freshly prepared takeout and
self-serve salads at Center on
Bar and Grill (4804 N Broadway)
gay sports bar and grill with fabulous weekend brunches, inexpensive
all-American fare until 10pm inside or out on the sidewalk cafe. All You Can Eat Thursday pasta specials, Fish Taco Fridays, half-price appetizers from 10pm to 1am on Fridays and Saturdays, and many daily drinks specials.
Mary's (5400 N Clark) gay
diner, 11-11 weekdays, with weekend brunch 10:30am to 3pm. Sports on TV, trivia games, gong shows, karaoke, cabaret and live soaps keep things always interesting.
Cafe (5951 N Broadway), a stellar restaurant serving spice authentic Thai cuisine and sushi from their large menu.
(5707 N Clark) new American-style restaurant and bakery with healthy cuisine for breakfast from 7am, (8 on weekends) and lunch. Famous for blackberry bliss cakes.
(5020 N Sheridan) breakfast and Saturday/Sunday brunch until 3pm;
dining in the salon six nights a week (closed Tuesdays) from the grill menu plus Friday night specials. Free wi-fi.
Winston's Internet Cafe
(5001 N Clark St) in the old Eagle location, now renovated, a friendly 24-hour coffeehouse next to Man's Country, with good cappuccino, sandwiches, free wi-fi and public computers.
Uno (29 E Ohio) Chicago's famed
deep-dish pizza, since 1943. A
classic, pleasantly different from the multitude it spawned. Also try Pizzaria Due (619 N Wabash Ave) around the corner.
Shop 'til you drop
The Magnificent Mile is a high-end
shopping district on Michigan Avenue
between Chicago River and Oak Street.
The Bucktown and Wicker Park
neighborhoods, both off North Milwaukee
Avenue, are full of boutiques,
galleries, theaters, eateries and
Elephant Resale (3645 N
second-hand shop, benefits gay
and AIDS groups.
Male (3418 N Halsted) salon and spa has been called "one of the best" in Chicago by Tabatha Coffey of Bravo TV.
Tattooing and Piercing Company
LTD (1017 W Belmont) does safe
branding and piercing with a gay-friendly outfit.
(3519 N Halsted) 'love' boutique has
leather, rubber, sex toys, potions and a good selection of x-rated dvd movies.
Mart (3459 N Halsted) is a warren of rooms brimming with rainbow
gifts, cards, jewelry, t-shirts, calendars, music, comic book action figures and fun toys.
Sport (3505 N Halsted) leather
and erotic retail store for bondage gear, paddles, floggers, toys, cock rings, pumps, stimulators, fetish videos and more.
Custom Leather (3920 N
Broadway) custom leather creations and
alterations from a Chicago leather legend.
Books (3251 N Broadway)
has focused on gay and lesbian titles since 1980 with good general public selections too. From the latest issues of gay magazines to Children's classics they cover the spectrum.
Elephant Resale (5228 N Clark)
sells pre-owned household items, books, music, kitchenware and clothing, etc, to support services for gay under or uninsured people and AIDS organizations.
Leathers (5005 N Clark St) is
a leather and adult retail store in Andersonville.
Barber (1481 W Balmoral) professional and personal service, good but inexpensive haircuts.
(5314 N Clark and 3162 N Broadway) stylishly distinctive clothing and accessories for guys to look good and feel confident. Casual and unpretentious store ambience.
6410 (6410 N Clark) leather and
Women and Children
First (5233 N. Clark St) is a women's bookstore.
Gym (5248 N Clark)
Andersonville's gay choice.
Club (3228 N
Halsted) gayest outpost in
(3727 N Broadway) cheapest
gay friendly gym in Lakeview.