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Explore Gay Accommodations in Crestwood

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Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport
Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport
Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport
Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport
Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport
Fabul'HostLGBTQ Flaglock
Gabriel
Private room • 17.9 miles from Crestwood
★ 4.99 (75)
Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport
Clothing optional accepted • Host shares gay local tips • Parking
#1 Hotel
Welcoming
Freehand Chicago
Freehand Chicago
Freehand Chicago
Freehand Chicago
Freehand Chicago
Approval 
Instant
Hotel room **** • 17.2 miles from Crestwood
★ 4.67 (3)
Freehand Chicago
🏆 Pride Points x3
Wi-Fi • Parking • Gym
Booked 19 times
Freshly Updated!
20 min 2 Boys Town EZ O'Hare Downtown, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ O'Hare Downtown, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ O'Hare Downtown, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ O'Hare Downtown, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ O'Hare Downtown, United Center, 50% Mo. Discount
LGBTQ Flaglock
John
Private room • 14.9 miles from Crestwood
★ 5 (17)
20 min 2 Boys Town EZ O'Hare Downtown, United Center, 50% Mo. Discount
Clothing optional accepted • Host shares gay local tips • Breakfast included
Conveniently located beautiful modern furnished condo!!
Conveniently located beautiful modern furnished condo!!
Conveniently located beautiful modern furnished condo!!
Conveniently located beautiful modern furnished condo!!
Conveniently located beautiful modern furnished condo!!
LGBTQ Flaglock
Saurin
Private room • 16.8 miles from Crestwood
★ 4.89 (9)
Conveniently located beautiful modern furnished condo!!
Air conditioning • Kitchen • Heating
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
LGBTQ Flaglock
Clemente
Entire place • 17.6 miles from Crestwood★ New
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Dedicated workspace • Air conditioning • Kitchen
#2 Hotel
Welcoming
HI Chicago Hostel
HI Chicago Hostel
HI Chicago Hostel
HI Chicago Hostel
HI Chicago Hostel
Approval 
Instant
Hotel room *** • 16.2 miles from Crestwood
★ 4.75 (4)
HI Chicago Hostel
🏆 Pride Points x3
Wi-Fi • Elevator • Wheelchair accessible
Booked 14 times
Hyde Park Haven: Exquisite BNB
Hyde Park Haven: Exquisite BNB
Hyde Park Haven: Exquisite BNB
Hyde Park Haven: Exquisite BNB
Hyde Park Haven: Exquisite BNB
LGBTQ Flaglock
Gloria
Entire place • 12.3 miles from Crestwood★ New
Hyde Park Haven: Exquisite BNB
Dedicated workspace • Air conditioning • Kitchen
#3 Hotel
Welcoming
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, Chicago
Approval 
Instant
Hotel room **** • 17 miles from Crestwood
★ 4.5 (2)
Club Quarters Hotel Wacker at Michigan, Chicago
🏆 Pride Points x3
Wi-Fi • Parking • Gym
Booked 9 times
Olga crib
Olga crib
Olga crib
Olga crib
Olga crib
LGBTQ Flaglock
Olga
Entire place • 16.7 miles from Crestwood★ New
Olga crib
Breakfast included • Dedicated workspace • Air conditioning
#4 Hotel
Welcoming
Acme Hotel Company Chicago
Acme Hotel Company Chicago
Acme Hotel Company Chicago
Acme Hotel Company Chicago
Acme Hotel Company Chicago
Approval 
Instant
Hotel room **** • 17.2 miles from Crestwood
★ 5 (1)
Acme Hotel Company Chicago
🏆 Pride Points x3
Wi-Fi • Parking • Gym
Booked 6 times
stunning single-family home
stunning single-family home
stunning single-family home
stunning single-family home
stunning single-family home
LGBTQ Flaglock
Morgan
Entire place • 17.8 miles from Crestwood★ New
stunning single-family home
Breakfast included • Dedicated workspace • Air conditioning
Welcoming
Aloft Chicago Downtown River North
Aloft Chicago Downtown River North
Aloft Chicago Downtown River North
Aloft Chicago Downtown River North
Aloft Chicago Downtown River North
Approval 
Instant
Hotel room *** • 17.1 miles from Crestwood
★ 4.8 (1)
Aloft Chicago Downtown River North
🏆 Pride Points x3
Wi-Fi • Parking • Gym
Booked 5 times
Lake Shore Drive.
Lake Shore Drive.
Lake Shore Drive.
Lake Shore Drive.
Lake Shore Drive.
LGBTQ Flaglock
Burchfield
Entire place • 17.9 miles from Crestwood★ New
Lake Shore Drive.
Breakfast included • Dedicated workspace • Air conditioning
Welcoming
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
Approval 
Instant
Hotel room ** • 16.1 miles from Crestwood
★ 4.5 (2)
Travelodge by Wyndham Downtown Chicago
🏆 Pride Points x3
Wi-Fi • Elevator
Booked 3 times
Basement Apartment close to everything!
Basement Apartment close to everything!
Basement Apartment close to everything!
Basement Apartment close to everything!
Basement Apartment close to everything!
LGBTQ Flaglock
Cesar
Entire place • 9.9 miles from Crestwood
★ 5 (3)
Basement Apartment close to everything!
Air conditioning • Heating • Dishwasher
Freshly Updated!
20 min 2 Boys Town EZ Downtown O'Hare, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ Downtown O'Hare, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ Downtown O'Hare, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ Downtown O'Hare, United Center, 50% Mo. Discount
20 min 2 Boys Town EZ Downtown O'Hare, United Center, 50% Mo. Discount
LGBTQ Flaglock
John
Private room • 14.9 miles from Crestwood
★ 5 (3)
20 min 2 Boys Town EZ Downtown O'Hare, United Center, 50% Mo. Discount
Clothing optional accepted • Host shares gay local tips • Breakfast included
Welcoming
The Whitehall Hotel - BW Premier Collection
The Whitehall Hotel - BW Premier Collection
The Whitehall Hotel - BW Premier Collection
The Whitehall Hotel - BW Premier Collection
The Whitehall Hotel - BW Premier Collection
Approval 
Instant
Hotel room *** • 17.7 miles from Crestwood
★ 5 (1)
The Whitehall Hotel - BW Premier Collection
🏆 Pride Points x3
Wi-Fi • Parking • Pets allowed
Booked 3 times
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