Pet Friendly Vacation Rentals in Chicago, IL

There are 67 pet friendly vacation rentals in Chicago. Need help deciding where to stay with your dog? You can browse the results below and filter by amenities to find the the perfect spot. All pet policy information is guaranteed and there are no booking fees!

Pet Friendly Quiet Comfort with Artsy Theme
Quiet Comfort with Artsy Theme Pet Policy This 2-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Pet Friendly Vintage Site in Lincoln Square
Vintage Site in Lincoln Square Pet Policy This 4-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Beach House Unit with Parking Pet Policy This 2-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Private Beachfront Retreat Pet Policy This 2-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Lyndale 2F Pet Policy This 3-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Hamlin Park #1 Pet Policy This 2-bedroom condo in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Western - Lincoln Square Pet Policy This 3-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Lyndale 1F Pet Policy This 2-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Oakdale 317 Pet Policy This 1-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Contemporary 2-Bedroom Wrigley Flat Pet Policy This 2-bedroom vacation rental in Chicago allows 2 dogs of any size for no additional fee. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
Winthrop 1 Pet Policy This 4-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Large 1-Br Modern Vintage Gem Pet Policy This 1-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Lyndale Bf Pet Policy This 2-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Historic Buena Park Large 3-Br Pet Policy This 3-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Wrigleyville 1/1 Condo Pet Policy This 1-bedroom condo in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Modern Wrigley 2-Bedroom Pet Policy This 2-bedroom vacation rental in Chicago allows 2 dogs of any size for no additional fee. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
Garden 1-Bedroom Next to Wrigley Field Pet Policy This 1-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
River North Rock And Roll Pet Policy This 2-bedroom apartment in Chicago is dog friendly! well-behaved dogs of any size are allowed for no additional fee. Sorry, no cats. Visit Website
Michigan Ave BnB Entire House Pet Policy This 6-bedroom house in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Lyndale 2R Pet Policy This 2-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Lyndale Br Pet Policy This 1-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
Winthrop 2 Pet Policy This 3-bedroom apartment in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
The Guesthouse Hotel 3 Bedroom Pet Policy This 3-room hotel in Chicago is dog friendly! Dogs of any size are allowed for no additional fee. Sorry, no cats. Visit Website
The Guesthouse Hotel Pet Policy This 1-bedroom condo in Chicago is dog friendly! Dogs of any size are allowed for no additional fee. Sorry, no cats. Visit Website