Chicago gay cruising spots

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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.

Will you always tell a friend where you’re going? There are plenty of drinks specials to keep you in the moon as you watch whatever sports are on the TV or have a friendly game of pool or darts with the new friends you'll inevitably make. They don’t tell friends where they’re going because they don’t want to admit they’re hooking up.

Cruise with caution. Venues like Sidetrack, Berlin, Roscoe’s, and Hydrate have security, other patrons around, and staff who can intervene if something goes wrong. Cruising the Belmont Rocks or Clark Street? Trust Your Gut (Especially After Midnight)

I can’t count how many times a client has told me, “I knew something felt off, but I ignored it.” That instinct—the tightening in your chest, the voice that says this doesn’t feel right—is your nervous system trying to protect you.

Cruising often happens late at night when you’ve been drinking.

That’s actually good news for safety—if you use it right.

Before meeting up with someone from an app:

Verify they’re real: ask for a live photo or FaceTime
Check their profile for red flags: no face pics, brand new account, overly pushy about meeting immediately
Share your location with a trusted friend using iPhone’s “Find My” or Google Maps location sharing
Tell someone where you’re going and who you’re meeting—send them a screenshot of the profile
Meet in a public place first if possible, even just for 10 minutes at Berlin or Scarlet before heading elsewhere

If someone refuses to verify their identity or gets angry when you ask basic safety questions, that’s your answer.

Pitchers of brightly coloured cocktails along with lively music from a range of genres make a vibrant and fun space for parties or getting together with friends for a night out. The easiest way to get around town is on the rapid transit trains.

You don’t have to figure this out alone.

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 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. Most importantly, have a sober friend you can text if you need a reality check on whether someone seems safe.

Final Thoughts: Cruising with Intention

Boystown exists because gay men refused to hide.

Know the History—And Why It Still Matters

Cruising has been part of gay male culture since long before Grindr. The gay scene is quite diverse with less attitude and snobbery than in some other cities. In 2021, several men were attacked and robbed in separate incidents near Halsted and Belmont. Chicago is the birth place of Blues and House music, which can be found nightly in small and large clubs, along with jazz, rock, techno and country.

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

Cruise with confidence. These spaces have history, but they also have risk.

If you’re going to cruise outdoor spots:

Go with a friend who can watch your back
Stay in areas with other people around
Avoid going after midnight when the area empties out
Keep your phone charged and in your hand
Don’t drink heavily before going—you need your wits about you
Let someone know where you are

The Rocks can be magical on a summer evening at sunset.

Will you only go home with someone you’ve talked to for at least 20 minutes? Plenty of themed events are on offer here, specific to leathermen, bears, and more.