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Gay Accommodations & Gay Bnbs in Maywood

Stay where you never have to explain yourself

Hosted by SeungLikes Biking, Beachlife, Massage

Shared space: bedroom • Maywood

Booked 1 time

5 (1)

Private Room

Kitchen • TV

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Stays near Maywood

These stays match your search but are located outside Maywood.

Hosted by Mike

Instant booking

Entire place • 11.2 miles from Maywood

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

Modern Elegance: 4BR Duplex w/ Free Garage Parking

Instant booking

Entire place • 4.9 miles from Maywood

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 • 1.6 miles from Maywood

4.8 (1)

Whispering Oaks Retreat!

5 Bedrooms • 5 Beds • 2 Bathrooms

Hosted by Mike

Instant booking

Entire place • 2.2 miles from Maywood

4.58 (1)

Pearly Gates w/ 2-Car Garage

3 Bedrooms • 3 Beds • 1 Bathroom

Hosted by Billy

2-Bed 2-Bath Apt | close to UC w/ Free Parking

Instant booking

Entire place • 8.3 miles from Maywood

4.7 (1)

2-Bed 2-Bath Apt | close to UC w/ Free Parking

2 Bedrooms • 2 Beds • 2 Bathrooms

Gay Welcoming Score

Rated by LGBTQ+ travelers

Instant booking

Private room • 11.4 miles from Maywood

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."

Gay Welcoming Score

Rated by LGBTQ+ travelers

Instant booking

Ranked#1 Hotel

Hotel *** • 10.8 miles from Maywood

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."

Gay Welcoming Score

Rated by LGBTQ+ travelers

Instant booking

Ranked#2 Hotel

Hotel **** • 11.1 miles from Maywood

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"

Gay Welcoming Score

Rated by LGBTQ+ travelers

Instant booking

Ranked#3 Hotel

Hotel *** • 11.1 miles from Maywood

Booked 27 times

4.88 (26)

HI Chicago Hostel

7 min · Doll House Entertainment (Gay Bars & Clubs)

Wi-Fi • Elevator • Wheelchair accessible

Stuart·5·Apr. 2025· "Nice location, nice place, friendly staff, clean and spacious rooms. Some of the dorm like rooms have a bathroom, and some don't. It's always a gamble sharing a room with strangers. It was my second time staying there, and I always got a mixture of good and bad guests. But I still would recommend it. Would like to try one of the other locations in another state someday."

100

Gay Welcoming Score

Rated by LGBTQ+ travelers