Chicago LGBTQ+ Week: Boystown Bars and Late Nights
This week in Chicago is based around Northalsted, America's first official gay village, with trips to Andersonville, Edgewater and the South Side. The days pair museums, archives and a community centre with gay bars, lounges and dance floors.
Day 1
Chicago · Day 1 — Northalsted (Boystown)
Start downtown at Millennium Park, then head north to Northalsted and the Center on Halsted to get your bearings.
Millennium Park — This iconic public park is home to famous art installations like Cloud Gate ('The Bean') and hosts various cultural events. · Center on Halsted — Chicago's main LGBTQ+ community centre on Halsted Street in Northalsted, with social services, youth and senior programmes, and events.
Legacy Walk — Free outdoor LGBT history walk along North Halsted Street in Chicago, with bronze plaques on rainbow pylons. · Howard Brown Health Center — Chicago's LGBTQ+ health centre on North Sheridan Road: primary care, HIV and STI testing, PrEP and trans care.
Small BYO bistro on North Halsted in Boystown serving chef Jon-Carl Lachman's Dutch- and French-leaning New American food.
Day 2
Chicago · Day 2 — Uptown
Spend the morning at the Art Institute of Chicago, then browse Milwaukee Avenue in Wicker Park and Bucktown.
Art Institute of Chicago — A world-renowned art museum boasting an extensive collection spanning centuries and cultures, from ancient artifacts to contemporary masterpieces. · Browse Milwaukee Avenue in Wicker Park / Bucktown — start at Ragstock, Buffalo Exchange · Unabridged Bookstore — Independent Lakeview bookstore on Broadway since 1980, with one of Chicago's best LGBTQ+ sections.
PrideArts — Chicago's LGBTQ+ theatre company, staging plays, musicals and cabaret at the Hoover-Leppen Theatre inside Center on Halsted.
Big Chicks — Uptown queer neighbourhood bar since 1986, with walls covered in the owner's art collection and a mixed, all-genders crowd. · Sofo — Neighborhood gay bar on North Clark in Andersonville with a big patio; open from afternoon on weekends.
Uptown breakfast and brunch spot next to Big Chicks, with big plates and a mixed queer crowd; open 9am-3pm daily.
Two other ways to do tonight ▾
Tours & Experiences in Chicago
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Day 3
Chicago · Day 3 — Northalsted (Boystown)
Northalsted gets the full day, from the streets of the gay village to menswear shopping at Cram Fashion.
Northalsted (Boystown) — Recognized as America's first official gay village, this vibrant neighborhood is a historic hub for LGBTQ+ culture, nightlife, and community. · CRAM Fashion — Menswear boutique on North Broadway in Lakeview, just north of Northalsted, selling slim-fit European-style clothing.
Boystown Rainbow Pylons — Rainbow pylons along North Halsted Street, installed by the City of Chicago in 1998 as official recognition of its gay neighbourhood. · Lucky Horseshoe Lounge — Long-running Boystown bar on North Halsted with male go-go dancers most nights.
Hydrate — Dance club in Northalsted (Boystown), Chicago, with DJs and late licence; usually no cover before midnight.
Small Italian restaurant on North Broadway at the edge of Boystown, open Wednesday to Sunday with weekend brunch.
Day 4
Chicago · Day 4 — Edgewater
Go far north to Edgewater for the Gerber/Hart Library's LGBTQ+ archives, then dance at Atmosphere in Andersonville.
Gerber/Hart Library — LGBTQ+ library and archives on West Granville Avenue in Chicago's far North Side, open a few afternoons and evenings a week.
Atmosphere (@mosphere) — Andersonville gay dance bar on North Clark Street with go-go dancers late in the week and a Sunday drag show. · Marty's Martini Bar — Small, dark-wood martini bar in Andersonville with a mostly gay neighborhood crowd; a place for conversation, not dancing.
Dinner then an easy evening.
Rustic seasonal Italian on North Clark Street in Andersonville, with a back patio in summer; dinner Wed to Sun.
Two other ways to do tonight ▾
Day 5
Chicago · Day 5
After a slow morning, spend the evening back on North Halsted at Scarlet and catch About Face Theatre, a queer company since 1995.
Slow start — coffee and a wander.
Scarlet — Lounge on North Halsted in Chicago's Northalsted, formerly The Gentry piano bar. · About Face Theatre — Chicago theatre company founded in 1995 that develops and stages new plays about gender and sexual identity. · Henry Gerber House — Old Town rowhouse where Henry Gerber founded the Society for Human Rights in 1924, the first documented US gay rights group. · Touche — Long-running leather bar on North Clark Street in Rogers Park, open until 4am, with a back room and a Sunday beer bust.
Dinner then an easy evening.
Mexican restaurant and tequila bar on North Broadway with 150+ tequilas and weekend brunch.
Day 6
Chicago · Day 6
Saturday stays in Boystown, with the North End sports bar near Wrigley Field and Little Jim's, the neighbourhood's first gay bar.
Slow start — coffee and a wander.
North End — Gay sports bar on North Halsted in Boystown, a few blocks from Wrigley Field; open daily, late on weekends. · Little Jim's Tavern — Boystown's first gay bar, a cheap neighbourhood tavern at Halsted and Cornelia that stays busy after other bars close. · Boystown — Halsted Street Strip — The stretch of North Halsted Street lined with rainbow pylons: the heart of Chicago's Northalsted gay district. · AIDS Garden Chicago — Lakefront AIDS memorial garden at Belmont Harbor with a 30-foot Keith Haring sculpture, on the site of the old Belmont Rocks.
Dinner then an easy evening.
Lakeview bar-restaurant on North Sheffield with a long beer list and cheap specials.
Day 7
Chicago · Day 7
End on the South Side at Jeffery Pub, a long-running Black gay bar, with a stop at Bughouse Square.
Slow start — coffee and a wander.
Jeffery Pub — Long-running Black gay bar on Chicago's South Side with a dance floor, late hours and a ladies' night on Fridays. · Bughouse Square (Washington Square Park) — Chicago's historic free-speech park, an early gay meeting place and starting point of the city's first Pride march on June 27, 1970. · AIDS Foundation of Chicago — HIV/AIDS policy, funding and services organisation founded in 1985, with offices in Chicago's Loop. · Baton Show Lounge — Chicago's long-running drag cabaret, now on North Broadway in Uptown, with seated shows Wednesday to Sunday.
Dinner then an easy evening.
Casual Thai noodle and rice spot on North Broadway in Northalsted, Chicago.
Two other ways to do tonight ▾
Practical Tips
- 1 See the Health & Safety block below for PrEP/testing access and practical norms.
- 2 Club doors: Clubs typically require a valid 21+ ID for entry, may have a cover charge payable by cash or card, and generally have a casual dress code.
- 3 Restaurants marked "book" fill up — reserve a day ahead.
Where to stay in
Hotel prices for your dates
via Stay22City essentials
- Millennium Park — This iconic public park is home to famous art installations like Cloud Gate ('The Bean') and hosts various cultural events.
- Art Institute of Chicago — A world-renowned art museum boasting an extensive collection spanning centuries and cultures, from ancient artifacts to contemporary masterpieces.
- Northalsted (Boystown) — Recognized as America's first official gay village, this vibrant neighborhood is a historic hub for LGBTQ+ culture, nightlife, and community.
Health & Safety
- PrEP & STI testing: Visitors can access PrEP and STI testing at Howard Brown Health, a major LGBTQ+ health center with multiple locations including Lakeview; services are often free or low-cost, and appointments are typically recommended.
- Emergency: 911
- Pharmacy: Many major pharmacy chains like Walgreens and CVS have 24-hour locations throughout the city.
- PDA: Public displays of affection for queer couples are generally safe and well-accepted, especially in LGBTQ+-friendly neighborhoods.
- Club doors: Clubs typically require a valid 21+ ID for entry, may have a cover charge payable by cash or card, and generally have a casual dress code.
- Cash vs card: Credit and debit cards are widely accepted everywhere, though cash can be useful for small purchases, tips, or some club cover charges.
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