PLACES TO STAY
Planning a visit to Chicago? Whether you're here for Market Days, the leather scene, or just soaking in the city vibes, we've got you covered with places to stay that are as welcoming as they are well-located.
Looking for something more personal? Check out our hand-picked Airbnbs — every one of them LGBTQ+ owned and operated. You’ll feel right at home knowing you're supporting queer hosts while enjoying a stylish, comfortable stay in the heart of the city.
Explore, unwind, and rest easy — Daddy’s got the hookup. 🖤
LGBTQ+ Owned Vacation Rentals
WHQ | Historic Flat w/ Poker Lounge & Parking
4BR Penthouse • 2 Min Walk to Wrigley • Parking
WHQ | Historic Flat w/ Poker Lounge & Parking
Just 2 minutes to Wrigley Field and 3 minutes to the Red Line (20 mins to downtown), this 1899 flat blends historic charm with modern design. Highlights include a hidden poker lounge, rare onsite paid parking, and access to a shared patio with firepit. Perfect for game days, city nights, and stylish group stays in the heart of Wrigleyville.
2BR Deco Flat | Walk to Wrigley + CTA
4BR Penthouse • 2 Min Walk to Wrigley • Parking
WHQ | Historic Flat w/ Poker Lounge & Parking
This 2BR, 1BA garden-level apartment combines comfort, convenience, and Art Deco style in the heart of Wrigleyville — just steps from Wrigley Field, dining, shopping, and public transit.
4BR Penthouse • 2 Min Walk to Wrigley • Parking
4BR Penthouse • 2 Min Walk to Wrigley • Parking
4BR Penthouse • 2 Min Walk to Wrigley • Parking
Just 2 minutes from Wrigley Field, this penthouse crowns a century-old building with historic charm and modern edge. Inside, you’ll find 4 bedrooms, 3 lounges, and a chef’s kitchen designed for groups. Host a poker night in the den, rack up in the billiards room, or unwind together — all with the rare bonus of onsite parking in the heart of Chicago’s North Side.
Villa Toscana and Dorothy's BnB
Nestled in the heart of Chicago's Boystown/Northalsted, this is the perfect location for stumbling home from the bars without having to leave Halsted. Save 10% off with Promocode: CHICAGODOMDADDY10.