Where to stay in Chicago
Northalsted (once called Boystown) in Lakeview is the center of gay Chicago, with Andersonville a few L stops north. Summer is the time to go, for Pride in June, Market Days in August, and the lakefront beaches.
Freehand Chicago
River North (E Ohio Street)
A design-minded hotel-hostel hybrid with private rooms and shared bunk rooms, plus a popular cocktail bar. A budget base downtown that's an easy Red Line ride to Northalsted, though reviews say service can be hit and miss.
Official siteBest Western Plus Hawthorne Terrace
N Broadway, Lakeview East
A plain, practical hotel whose big selling point is location: it's a couple of blocks from the Halsted Street bars and close to the lakefront. Recent reviewers call it overpriced, so book it for the address, not the rooms.
Official siteHotel Zachary
N Clark Street, Wrigleyville
A highly rated boutique hotel across from Wrigley Field, near the Red Line and a short walk from Northalsted. A comfortable, well-run choice, though rates jump on Cubs game days.
Official siteThe Robey
W North Avenue, Wicker Park
A boutique hotel in a restored Art Deco tower at the Wicker Park six-corner intersection, surrounded by bars, restaurants and shops. It suits travelers who'd rather explore Chicago's neighborhood nightlife than stay downtown.
Official sitePlan around these
International Mr. Leather
Chicago, IL · Dates TBA TBA, Memorial Day weekend
The world's leather contest and a huge market downtown.
Chicago Pride Parade
Chicago, IL · Dates TBA Expected Sun Jun 27 (last Sunday of June)
One of the country's biggest parades, through Lakeview and Northalsted.
Northalsted Market Days
Chicago, IL · Dates TBA TBA, August
Huge street festival on Halsted in Boystown.
Listings checked against official sites in 2025–26. Policies and prices change, so confirm before you book. We don't take money from hotels.