Pet Friendly Vacation Rentals
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    Pet Friendly Vacation Rentals in Chicago, IL

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    There are 276 pet friendly vacation rentals in Chicago. Need help to decide where to stay with your dog? You can browse the results below and filter by amenities to find the perfect spot. All pet policy information is guaranteed and there are no booking fees!

    Pet Friendly Lincoln Park 201
    $333
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 4

    Lincoln Park 201

    5.0 Chicago, IL
    Lincoln Park 201 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
    $287
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    Lincoln Park 203

    4.8 Chicago, IL
    Lincoln Park 203 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
    $200
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 2

    City Sanctuary Chicago

    5.0 Chicago, IL
    City Sanctuary Chicago Pet Policy This 1-bedroom house in Chicago allows 2 dogs of any size for no additional fee. Cats may also be allowed by request. Visit Website
    $260
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 2

    Urban Forest Retreat

    5.0 Chicago, IL
    Urban Forest Retreat Pet Policy This 1-bedroom vacation rental in Chicago allows 2 dogs of any size for no additional fee. Cats may also be allowed by request. Visit Website
    $365
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    River North Rock and Roll

    4.8 Chicago, IL
    River North Rock and Roll Pet Policy This 2-bedroom apartment in Chicago allows dogs of any size for no additional fee. Pets must be housebroken. Sorry, no cats. Visit Website
    $152
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 2

    Decorated 1BR Apartment with Natural Light

    4.0 Chicago, IL
    Decorated 1BR Apartment with Natural Light Pet Policy This 1-bedroom vacation rental in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $156
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 4

    Designer 2BR in Festive Boystown

    4.2 Chicago, IL
    Designer 2BR in Festive Boystown Pet Policy This 1-bedroom vacation rental in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $169
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    River Norths Finest

    4.6 Chicago, IL
    River Norths Finest Pet Policy This 2-bedroom vacation rental in Chicago allows dogs of any size for no additional fee. Pets must be crate-trained and housebroken. Sorry, no cats. All pets must be approved in advance. Visit Website
    $259
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 4

    H2C Designer 2BR - Feel the Local Vibe

    4.1 Chicago, IL
    H2C Designer 2BR - Feel the Local Vibe Pet Policy This 1-bedroom vacation rental in Chicago is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $573
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 7

    The Guesthouse Hotel 3 Bedroom

    4.9 Chicago, IL
    The Guesthouse Hotel 3 Bedroom Pet Policy This 3-bedroom hotel room in Chicago allows dogs of any size for no additional fee. Sorry, no cats or aggressive dogs. Visit Website
    $137
    No Pet Fee
    Small Dogs Only
    2+ Pets Allowed
    Sleeps 8

    The Avondale Guesthouse

    4.8 Chicago, IL
    The Avondale Guesthouse Pet Policy This 3-bedroom house in Chicago allows 2 dogs under 20 lbs for no additional fee. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
    $590
    No Pet Fee
    Small Dogs Only
    2+ Pets Allowed
    Sleeps 8

    Large Historic Home Minutes from Downtown Chicago

    5.0 Chicago, IL
    Large Historic Home Minutes from Downtown Chicago Pet Policy This 5-bedroom house in Chicago allows 3 dogs under 50 lbs for no additional fee. Cats may also be allowed by request. Visit Website
    $228
    No Pet Fee
    Small Dogs Only
    2+ Pets Allowed
    Sleeps 5

    Contemporary 2BR Flat Right Next to Wrigley Field

    4.6 Chicago, IL
    Contemporary 2BR Flat Right Next to Wrigley Field Pet Policy This 2-bedroom apartment in Chicago allows 2 dogs under 50 lbs for no additional fee. Cats are also welcome. Visit Website
    $402
    No Pet Fee
    Big Dogs Allowed
    1 Pet Max
    Sleeps 5

    The Guesthouse Hotel

    5.0 Chicago, IL
    The Guesthouse Hotel Pet Policy This 2-bedroom condo in Chicago allows 1 dog of any size for no additional fee. Sorry, no cats. Visit Website
    $155
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    Logan Square First Floor Apartment

    4.9 Chicago, IL
    Logan Square First Floor Apartment Pet Policy This 2-bedroom vacation rental in Chicago allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request. Visit Website
    $86
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 2

    River West Apartment with Rooftop & Gym

    5.0 Chicago, IL
    River West Apartment with Rooftop & Gym Pet Policy This 1-bedroom apartment in Chicago allows dogs of any size for an additional fee of $25 per pet, per stay. There is also a $500 refundable deposit. Cats may also be allowed by request, but all pets must be approved in advance. Breed restrictions apply. Visit Website
    $165
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 5

    Complete Bucktown/Logan Square Apartment

    5.0 Chicago, IL
    Complete Bucktown/Logan Square Apartment Pet Policy This 2-bedroom apartment in Chicago allows 2 dogs of any size for an additional fee of $20 per pet, per night. Cats may also be allowed by request. Visit Website
    $135
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    3BR Close to Transportation & Downtown

    5.0 Chicago, IL
    3BR Close to Transportation & Downtown Pet Policy This 3-bedroom apartment in Chicago allows 2 dogs of any size for an additional fee of $20 per pet, per stay. Cats may also be allowed by request. Visit Website
    $240
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 3

    Cozy 1-Bedroom Apartment

    5.0 Chicago, IL
    Cozy 1-Bedroom Apartment Pet Policy This 1-bedroom vacation rental in chicago allows dogs of any size for an additional fee of $15 per pet, per night. Sorry, no cats. Visit Website
    $89
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 13

    Jamie's Place

    5.0 Chicago, IL
    Jamie's Place Pet Policy This 2-bedroom vacation rental in Chicago allows 2 dogs of any size for an additional fee of $20 per pet, per night. Sorry, no cats. Pet bowls and a bed are provided. The yard is fenced. Visit Website
    Chicago, IL, US