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Explore Gay Accommodations in Countryside

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Sunny & spacious Uptown bedroom w/ private bath
Sunny & spacious Uptown bedroom w/ private bath
Sunny & spacious Uptown bedroom w/ private bath
Sunny & spacious Uptown bedroom w/ private bath
Sunny & spacious Uptown bedroom w/ private bath
LGBTQ Flaglock
James
Private room • 17.3 miles from Countryside
★ 5 (131)
Sunny & spacious Uptown bedroom w/ private bath
Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby
Uptown private bedroom and bathroom
Uptown private bedroom and bathroom
Uptown private bedroom and bathroom
Uptown private bedroom and bathroom
Uptown private bedroom and bathroom
Fabul'HostLGBTQ Flaglock
Cameron
Private room • 16.9 miles from Countryside
★ 4.99 (108)
Uptown private bedroom and bathroom
Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby
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 • 12.9 miles from Countryside
★ 4.99 (73)
Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport
Clothing optional accepted • Host shares gay local tips • Parking
Private Room near Andersonville
Private Room near Andersonville
Private Room near Andersonville
Private Room near Andersonville
LGBTQ Flaglock
JP
Private room • 16.8 miles from Countryside
★ 4.98 (50)
Private Room near Andersonville
Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby
Cozy Stay in Vibrant Albany Park for a Memorable Experience
Cozy Stay in Vibrant Albany Park for a Memorable Experience
Cozy Stay in Vibrant Albany Park for a Memorable Experience
Cozy Stay in Vibrant Albany Park for a Memorable Experience
Cozy Stay in Vibrant Albany Park for a Memorable Experience
LGBTQ Flaglock
Angel
Private room • 14.6 miles from Countryside★ New
Cozy Stay in Vibrant Albany Park for a Memorable Experience
Host shares gay local tips • LGBTQ+ venues nearby • Gym nearby
Freshly Updated!
Heart of Andersonville Modern Private room, Home away from Home
Heart of Andersonville Modern Private room, Home away from Home
Heart of Andersonville Modern Private room, Home away from Home
Heart of Andersonville Modern Private room, Home away from Home
Heart of Andersonville Modern Private room, Home away from Home
Fabul'HostLGBTQ Flaglock
Tommy
Private room • 17.2 miles from Countryside
★ 5 (38)
Heart of Andersonville Modern Private room, Home away from Home
Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby
Your Perfect Getaway in Chicago Awaits
Your Perfect Getaway in Chicago Awaits
Your Perfect Getaway in Chicago Awaits
Your Perfect Getaway in Chicago Awaits
Your Perfect Getaway in Chicago Awaits
LGBTQ Flaglock
Angel
Entire place • 10.1 miles from Countryside★ New
Your Perfect Getaway in Chicago Awaits
Host shares gay local tips • LGBTQ+ venues nearby • Gym nearby
Clothing optional Chicago garden level in-law suite
Clothing optional Chicago garden level in-law suite
Clothing optional Chicago garden level in-law suite
Clothing optional Chicago garden level in-law suite
Clothing optional Chicago garden level in-law suite
LGBTQ Flaglock
Tony
Entire place • 16.4 miles from Countryside
★ 4.88 (41)
Clothing optional Chicago garden level in-law suite
Host shares gay local tips • Gym nearby • Air conditioning
Experience Luxury and Convenience in the Heart of Chicago
Experience Luxury and Convenience in the Heart of Chicago
Experience Luxury and Convenience in the Heart of Chicago
Experience Luxury and Convenience in the Heart of Chicago
Experience Luxury and Convenience in the Heart of Chicago
LGBTQ Flaglock
Angel
Entire place • 12.6 miles from Countryside★ New
Experience Luxury and Convenience in the Heart of Chicago
Host shares gay local tips • LGBTQ+ venues nearby • Gym nearby
Spacious bedroom with private bath and sitting area in modern condo
Spacious bedroom with private bath and sitting area in modern condo
Spacious bedroom with private bath and sitting area in modern condo
Spacious bedroom with private bath and sitting area in modern condo
Spacious bedroom with private bath and sitting area in modern condo
LGBTQ Flaglock
Mike
Private room • 17.3 miles from Countryside
★ 4.97 (36)
Spacious bedroom with private bath and sitting area in modern condo
Clothing optional accepted • Air conditioning • Heating
Discover Downtown Chicago at Aloft Chicago Mag Mile - 2 Queen Room
Discover Downtown Chicago at Aloft Chicago Mag Mile - 2 Queen Room
Discover Downtown Chicago at Aloft Chicago Mag Mile - 2 Queen Room
Discover Downtown Chicago at Aloft Chicago Mag Mile - 2 Queen Room
Discover Downtown Chicago at Aloft Chicago Mag Mile - 2 Queen Room
LGBTQ Flaglock
Angel
Entire place • 15.3 miles from Countryside★ New
Discover Downtown Chicago at Aloft Chicago Mag Mile - 2 Queen Room
Host shares gay local tips • LGBTQ+ venues nearby • Gym nearby
Lakeview Location, Location, Location!! (Parking Possible)
Lakeview Location, Location, Location!! (Parking Possible)
Lakeview Location, Location, Location!! (Parking Possible)
Lakeview Location, Location, Location!! (Parking Possible)
Lakeview Location, Location, Location!! (Parking Possible)
LGBTQ Flaglock
Roger
Private room • 16.1 miles from Countryside
★ 5 (30)
Lakeview Location, Location, Location!! (Parking Possible)
Host shares gay local tips • LGBTQ+ venues nearby • Gym nearby
Unwind in Style at Roscoe Village Guesthouse, Close to Wrigley Field!
Unwind in Style at Roscoe Village Guesthouse, Close to Wrigley Field!
Unwind in Style at Roscoe Village Guesthouse, Close to Wrigley Field!
Unwind in Style at Roscoe Village Guesthouse, Close to Wrigley Field!
Unwind in Style at Roscoe Village Guesthouse, Close to Wrigley Field!
LGBTQ Flaglock
Angel
Entire place • 15 miles from Countryside★ New
Unwind in Style at Roscoe Village Guesthouse, Close to Wrigley Field!
Host shares gay local tips • LGBTQ+ venues nearby • Gym nearby
Freshly Updated!
Walk to Andersonville Gay Bars, Theatre & Restaurants.
Walk to Andersonville Gay Bars, Theatre & Restaurants.
Walk to Andersonville Gay Bars, Theatre & Restaurants.
Walk to Andersonville Gay Bars, Theatre & Restaurants.
Walk to Andersonville Gay Bars, Theatre & Restaurants.
Fabul'HostLGBTQ Flaglock
Gerard
Private room • 18.1 miles from Countryside
★ 5 (32)
Walk to Andersonville Gay Bars, Theatre & Restaurants.
Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby
Private bedroom + bathroom in 3 bdr condo
Private bedroom + bathroom in 3 bdr condo
Private bedroom + bathroom in 3 bdr condo
Private bedroom + bathroom in 3 bdr condo
Private bedroom + bathroom in 3 bdr condo
LGBTQ Flaglock
Baris
Private room • 16.7 miles from Countryside
★ 4.96 (23)
Private bedroom + bathroom in 3 bdr condo
Clothing optional accepted • Host shares gay local tips • Air conditioning
UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)
UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)
UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)
UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)
UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)
LGBTQ Flaglock
Tomasso
Private room • 17.1 miles from Countryside
★ 4.88 (17)
UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)
Parking • Air conditioning • Kitchen
#1 Hotel
Friendly
Chicago Getaway Hostel
Chicago Getaway Hostel
Chicago Getaway Hostel
Chicago Getaway Hostel
Chicago Getaway Hostel
Approval 
Instant
Hotel room *** • 15.6 miles from Countryside
★ 4.5 (4)
Chicago Getaway Hostel
🏆 Pride Points x3
Parking • Elevator • Smoking allowed
Booked 20 times
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With misterb&b, experience a more welcoming world. From private rooms and apartments to LGBTQ-friendly hotels and LGBTQ+ vacation rentals, you have the option to stay in the heart of gay districts as well as other neighborhoods in the places you visit. A loft in Soho, a shared room in Barcelona or the Castro, a gay-friendly hotel in Le Marais or in Chelsea, experience misterb&b in all worldwide gay travel destinations! Activate weere on your profile and connect with other misterb&b travelers at your destination city or hotel! Problems with misterb&b? Please refer to our Help Center. And whether you type gay bnb, gaybnb, mister b&b, mrb&b, mister b and b or misterbandb when you search for us, there's only one misterb&b! misterb&b is not affiliated, endorsed, or otherwise associated with Airbnb, neither with misterbnb, mrbnb or mr bnb.

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