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Gay Accommodations & Gay Bnbs in Hillside
Stay where you never have to explain yourself
Keep searching in the city: Trusted gay-friendly stays
Gay travel is a niche market, which is why our inventory here is sometimes limited. By booking one of these LGBTQ+ friendly stays, you directly help misterb&b fund its mission: recruiting new gay hosts and covering the complex legal and regulatory costs we face. Give your stay meaning - book your favorite below!
Certified Gay-FriendlySigned a non-discrimination policy.
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Instant bookingHotel *** • Hillside
4.32 (1)
Best Western Plus Chicago Hillside
Wi-Fi • Parking • Gym
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel ** • Hillside
4.4 (1)
Holiday Inn Express & Suites Chicago West-O'Hare Arpt Area by IHG
Wi-Fi • Pool • Parking
Hosted by Mike
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Entire place • Hillside
4.59 (1)
The Gathering House & Cinema
5 Bedrooms • 6 Beds • 3 Bathrooms
Certified Gay-FriendlySigned a non-discrimination policy.
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Hotel *** • Hillside
3.64 (1)
MainStay Suites Chicago Hillside
Wi-Fi • Parking • Pets allowed
Stays near Hillside
These stays match your search but are located outside Hillside.
Hosted by Mike
Instant booking
Entire place • 14.3 miles from Hillside
4.65 (1)
The Huron Loft | Near Magnificent Mile
9 min · Frenchy’s (Gay Saunas & Cruising)1 Bedroom • 1 Bed • 1 Bathroom
Hosted by Mike
Instant booking
Entire place • 7.9 miles from Hillside
Booked 3 times
5 (1)
Modern Elegance: 4BR Duplex w/ Free Garage Parking
4 Bedrooms • 5 Beds • 2 Bathrooms
Jarred·5·Jul. 2026· "My friends and I had a great time here! The home was clean, with every room accurately reflecting what we saw in pictures. We received communications prior to our stay about check-in procedures. The home is about 30-40 minutes from the gay district, Northalsted. Front gate remains locked, so entrance can only be from the back of the house through the garage. Amenities worked great! Washer/dryer was simple to use, AC worked great, however the dishwasher's top rack was missing support, but did not interfere with completing a cycle."
Hosted by Mike
Instant booking
Entire place • 4.6 miles from Hillside
4.8 (1)
Whispering Oaks Retreat!
5 Bedrooms • 5 Beds • 2 Bathrooms
Hosted by Mike
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Entire place • 5.1 miles from Hillside
4.58 (1)
Pearly Gates w/ 2-Car Garage
3 Bedrooms • 3 Beds • 1 Bathroom
Hosted by Billy
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Entire place • 11.4 miles from Hillside
4.7 (1)
2-Bed 2-Bath Apt | close to UC w/ Free Parking
2 Bedrooms • 2 Beds • 2 Bathrooms
92Gay Welcoming ScoreRated by LGBTQ+ travelers
Instant booking
Private room • 14 miles from Hillside
Booked 45 times
4.58 (45)
Hollywood Rentals LLC
5 min · Fireside (Gay Restaurants)Gay District • Wi-Fi
Kannon·5·Jun. 2026· "If you're looking for a cheap place for a weekend, this is great! you get the code day of, in a nice part of the city. would recommend! i will say, the number to the place is not very responsive, so don't expect much until day of your stay."
99Gay Welcoming ScoreRated by LGBTQ+ travelers
Instant booking
Ranked#1 Hotel
Hotel *** • 13.6 miles from Hillside
Booked 27 times
4.93 (27)
Wrigley Hostel - Chicago
5 min · Pick Me Up Cafe & All Nite Express Lounge (Gay Restaurants)Wi-Fi • Parking • Smoking allowed
Arturo·5·Aug. 2026· "Very good location and pleasant to stay for a few days."
98Gay Welcoming ScoreRated by LGBTQ+ travelers
Instant booking
Ranked#2 Hotel
Hotel **** • 14.2 miles from Hillside
Booked 31 times
4.9 (31)
Freehand Chicago
10 min · Hubbard Books (Gay Saunas & Cruising)Wi-Fi • Parking • Gym
Jean·5·Oct. 2025· "I definitely recommend this place, excellent location"