Pet Friendly Vacation Rentals

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Pet Friendly Vacation Rentals

Pet Friendly Vacation Rentals in Chicago, IL

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There are 270 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 #1807 Stu-Q Superior

Big Dogs Allowed

2+ Pets Allowed

#1807 Stu-Q Superior

4.0 Chicago, IL

#1807 Stu-Q Superior Pet Policy

This vacation rental in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Breed restrictions apply, and pets must be approved in advance.

Big Dogs Allowed

2+ Pets Allowed

The Historic Chicago Home

4.8 Chicago, IL

The Historic Chicago Home Pet Policy

Dogs of any size are allowed at this 7-bedroom vacation rental in Chicago for an additional fee of $10 per pet, per night. Cats are also accepted. Please note that pet birds live on the property.

Big Dogs Allowed

2+ Pets Allowed

Urban Oasis in Logan Square

5.0 Chicago, IL

Urban Oasis in Logan Square Pet Policy

Dogs of any size are allowed at this 2-bedroom house in Chicago for an additional fee of $150 per pet, per stay. Cats may also be allowed by request.

Small Dogs Only

Gorgeous 2BR in Amazing Location Near Beach

4.7 Chicago, IL

Gorgeous 2BR in Amazing Location Near Beach Pet Policy

This 2-bedroom house in Chicago allows 1 dog under 20 lbs for no additional fee. Cats are also welcome.

Big Dogs Allowed

2+ Pets Allowed

3/2 Condo with Fenced Yard

4.8 Chicago, IL

3/2 Condo with Fenced Yard Pet Policy

This 3-bedroom vacation rental in Chicago allows dogs of any size for an additional fee of $150 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance.

Small Dogs Only

2+ Pets Allowed

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

4.9 Chicago, IL

Inspiring Stone Grotto Sleeps 10-20 & Free Parking Pet Policy

This 4-bedroom vacation rental in Chicago allows 2 dogs under 50 lbs for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Lincoln Park 2BR Condo with Mid Century Flair

4.9 Chicago, IL

Lincoln Park 2BR Condo with Mid Century Flair Pet Policy

This 2-bedroom condo in Chicago allows dogs of any size for an additional fee of $250 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

Apartment #1611 KQ2T

4.9 Chicago, IL

Apartment #1611 KQ2T Pet Policy

This vacation rental in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Breed restrictions apply, and pets must be approved in advance. There is an on-site dog park and designated dog walking areas.

Big Dogs Allowed

2+ Pets Allowed

Quaint 2-Bedroom Condo With Rooftop Deck

4.8 Chicago, IL

Quaint 2-Bedroom Condo With Rooftop Deck Pet Policy

Dogs of any size are allowed at this 2-bedroom vacation rental in Chicago for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

#1905 K Superior

4.5 Chicago, IL

#1905 K Superior Pet Policy

This vacation rental in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Breed restrictions may apply.

Big Dogs Allowed

2+ Pets Allowed

El Motel Dos

4.9 Chicago, IL

El Motel Dos Pet Policy

This 4-bedroom vacation rental in Chicago allows 2 dogs of any size for an additional fee of $150 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

3BR Unit Steps to the Beach & Close to Loyola

5.0 Chicago, IL

3BR Unit Steps to the Beach & Close to Loyola Pet Policy

This 3-bedroom apartment in Chicago allows 3 dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

Kasa 1/1 Chicago River North

5.0 Chicago, IL

Kasa 1/1 Chicago River North Pet Policy

This apartment in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome.

Big Dogs Allowed

2+ Pets Allowed

Chicago Basement Flat

4.5 Chicago, IL

Chicago Basement Flat Pet Policy

This vacation rental in Chicago allows dogs of any size for an additional fee of £82 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

Apartment #1620 K2T

4.8 Chicago, IL

Apartment #1620 K2T Pet Policy

This 2-bedroom vacation rental in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Breed restrictions apply, and pets must be approved in advance. There is an on-site dog park and designated dog walking areas.

Big Dogs Allowed

2+ Pets Allowed

Hello Chicago

5.0 Chicago, IL

Hello Chicago Pet Policy

This 5-bedroom vacation rental in Chicago allows dogs of any size for an additional fee of $300 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Chicago Main House

4.6 Chicago, IL

Chicago Main House Pet Policy

This 4-bedroom vacation rental in Chicago allows dogs of any size for an additional fee of £82 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

2/2 Condo with Fireplace

4.8 Chicago, IL

2/2 Condo with Fireplace Pet Policy

This 2-bedroom condo in Chicago allows 2 dogs of any size for an additional fee of $135 per pet, per stay. Sorry, no cats.

Big Dogs Allowed

1/1 Apartment with Internet

4.9 Chicago, IL

1/1 Apartment with Internet Pet Policy

This 1-bedroom apartment in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome.

Big Dogs Allowed

#1108 Chicago Studio

5.0 Chicago, IL

#1108 Chicago Studio Pet Policy

This vacation rental in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Breed restrictions apply, and pets must be approved in advance.

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Chicago, IL, US