Chicago gay cruising spots

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Will you only go home with someone you’ve talked to for at least 20 minutes? Legitimate people understand why gay men need to be cautious.

5. Touche has a neighbourhood bar vibe with draught beers on tap, pool table, darts, and pinball machines, but it also offers a less traditional back room where you can spend time with the leathermen you just met...

Bear, Older Crowd, Fetish, Cruising

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Sidetrack

Sidetrack is the biggest and one of the most popular gay bars in Chicago.

But it’s also isolated, especially after dark, with limited lighting and plenty of places for someone with bad intentions to corner you.

Same goes for cruising on Clark Street near the Hollywood Beach area or parts of Lincoln Park. Spring and fall offer moderate safety, but always check sunset times and plan accordingly.

Is it safer to cruise at bars or outdoor spots?

Bars are generally safer than outdoor cruising spots.

Cruise with caution. Our practice has been serving the LGBTQ+ community in Boystown in Chicago for over 20 years, and we get it.

Gay Map of

The GayMapper interactive gay map of Chicago, Illinois helps you locate all the gay bars, gay clubs, gay events and gay cruising spots in Boystown and elsewhere.

But we honor that legacy by taking care of each other, not by pretending the risks don’t exist.

Cruise with confidence.

International Mr. Leather is held in Chicago each year on the Memorial Day weekend and Chicago's pride festival takes place every year the last weekend in June. That guy who seems charming at 1 AM might have been setting off alarm bells at 10 PM. If someone’s pushing you to leave quickly, getting aggressive when you set boundaries, or giving inconsistent answers about where they live or want to go, trust that feeling.

Practical tip: Before you go out, decide on your boundaries while you’re still sober.

That historical context should inform how we move through these spaces now: with awareness, caution, and respect for the vulnerability inherent in seeking connection.

2. This bar is dark and divey with an old school charm that has remained untouched by the upscale modernity of the street below. Click on the map to find out more information about each venue.

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Chicago Gay Bars

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Winter months (November – March) are riskier because fewer people are on the streets, darkness comes earlier, and icy sidewalks can make it harder to move quickly if needed. Write it down if you need to. If you’re at a bar and someone’s buying you drinks, watch the bartender make them—never accept a drink that’s been out of your sight.

But here’s the truth: strangers asking for help late at night in Boystown are often not who they seem.

Better response: Offer to call someone for them, suggest they go into a bar or business for assistance, or simply say “I’m sorry, I can’t help” and keep moving. Today’s risks look different—but they’re still real.

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.

Second Story Bar

As the name suggests, Second Story Bar is hidden away above a restaurant in the River North area of Chicago.

The gay scene is quite diverse with less attitude and snobbery than in some other cities. Avoid “Helping” Strangers with Problems

This is a classic setup that I’ve seen play out too many times: You’re outside Hydrate or walking down Halsted, and someone approaches asking for help. Another highlight of the summer festival season is North Halsted Market Days, a street festival held in late July or early August.

Mixed crowds gather in the low-lit, rustic-industrial setting complete with two bars and a dance floor.

The North End

The North End is a long-running gay sports bar in Boystown that provides a laidback and unpretentious atmosphere.