Explore Gay Accommodations in Hillside

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Sunny & spacious Uptown bedroom w/ private bath

James

Private room • 14.2 miles from Hillside

★ 5 (131)

Sunny & spacious Uptown bedroom w/ private bath

Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby

Cameron

Private room • 13.9 miles from Hillside

★ 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

Gabriel

Private room • 10.6 miles from Hillside

★ 4.99 (75)

Comfy, Relaxing Private Bedroom easy to get to from O’Hare Airport

Clothing optional accepted • Host shares gay local tips • Parking

Private room • 13.6 miles from Hillside

★ 4.98 (52)

Private Room near Andersonville

Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby

Freshly Updated!

BOYSTOWN/WRIGLEY LARGE PRIVATE BEDROOM! UNIQUE, CLEAN, FRIENDLY APARTM

Mike

Private room • 14 miles from Hillside★ New

BOYSTOWN/WRIGLEY LARGE PRIVATE BEDROOM! UNIQUE, CLEAN, FRIENDLY APARTM

Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby

Heart of Andersonville Modern Private room, Home away from Home

Tommy

Private room • 13.9 miles from Hillside

★ 5 (42)

Heart of Andersonville Modern Private room, Home away from Home

Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby

Olga

Approval

Instant

Entire place • 12.3 miles from Hillside★ New

Olga crib

Breakfast included • Dedicated workspace • Air conditioning

Clothing optional Chicago garden level in-law suite

Tony

Entire place • 12.9 miles from Hillside

★ 4.88 (41)

Clothing optional Chicago garden level in-law suite

Host shares gay local tips • Gym nearby • Air conditioning

Morgan

Approval

Instant

Entire place • 10.5 miles from Hillside★ New

stunning single-family home

Breakfast included • Dedicated workspace • Air conditioning

Spacious bedroom with private bath and sitting area in modern condo

Mike

Private room • 14.2 miles from Hillside

★ 4.97 (36)

Spacious bedroom with private bath and sitting area in modern condo

Clothing optional accepted • Air conditioning • Heating

Freshly Updated!

Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D

Clemente

Entire place • 14.2 miles from Hillside★ New

Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D

Dedicated workspace • Air conditioning • Kitchen

Lakeview Location, Location, Location!! (Parking Possible)

Roger

Private room • 13.8 miles from Hillside

★ 5 (29)

Lakeview Location, Location, Location!! (Parking Possible)

Host shares gay local tips • LGBTQ+ venues nearby • Gym nearby

Gloria

Entire place • 15.9 miles from Hillside★ New

Hyde Park Haven: Exquisite BNB

Dedicated workspace • Air conditioning • Kitchen

Freshly Updated!

Walk to Andersonville Gay Bars, Theatre & Restaurants.

Gerard

Private room • 14.6 miles from Hillside

★ 5 (32)

Walk to Andersonville Gay Bars, Theatre & Restaurants.

Clothing optional accepted • Host shares gay local tips • LGBTQ+ venues nearby

Freshly Updated!

Private bedroom + bathroom in 3 bdr condo

Baris

Private room • 13.9 miles from Hillside

★ 4.96 (23)

Private bedroom + bathroom in 3 bdr condo

Clothing optional accepted • Host shares gay local tips • Air conditioning

#1 Hotel

Welcoming

Approval

Instant

Hotel room *** • 13.7 miles from Hillside

★ 4.5 (4)

Chicago Getaway Hostel

🏆 Pride Points x3

Parking • Elevator • Smoking allowed

Booked 20 times

UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)

Tomasso

Private room • 14.1 miles from Hillside

★ 4.88 (17)

UPTOWN ROW HOUSE-SPACIOUS PRIVATE SHARED ROOM(S)

Parking • Air conditioning • Kitchen

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