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

    There are 165 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. BringFido members never pay a booking fee, and their reservations are backed by our Pet Friendly Guarantee!

    $99+
    No pet fee
    Big dogs OK
    2+ pets OK

    Pet-Friendly Airbnb Rentals

    Chicago, IL
    $558
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 6

    Wrigleyville 1/1 Condo

    5.0 Chicago, IL
    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
    $276
    No pet fee
    Big dogs OK
    1 pet max
    Sleeps 6

    River Norths Finest

    4.7 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
    $313
    No pet fee
    10 kg max
    2 pets max
    Sleeps 6

    The Avondale Guesthouse

    4.9 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
    $216
    +$25 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 6

    Logan Square First Floor Apartment

    5.0 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
    $160
    +$20/pet/night
    Big dogs OK
    2 pets max
    Sleeps 10

    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
    Inquire
    +$50/pet/night
    Big dogs OK
    2+ pets OK

    Chicago Townhome

    Chicago, IL
    Chicago Townhome Pet Policy This 4-bedroom house in Chicago allows pets of any size for an additional fee of $50 per pet, per night. Both dogs and cats are welcome. See Details
    $744
    +$150 per pet
    Big dogs OK
    2 pets max
    Sleeps 12

    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. Visit Website
    $967
    +$10/pet/night
    Big dogs OK
    2+ pets OK
    Sleeps 12

    The Historic Chicago Home

    4.9 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. Visit Website
    $258
    +$25 per pet
    25 kg max
    2 pets max
    Sleeps 20

    Inspiring Stone Grotto Sleeps 10-20 & Free Parking

    5.0 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. Visit Website
    $196
    +$135 per pet
    Big dogs OK
    2 pets max
    Sleeps 6

    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. Visit Website
    $322
    +$95 per pet
    Big dogs OK
    2 pets max
    Sleeps 5

    Urban Riverhouse in the Woods

    5.0 Chicago, IL
    Urban Riverhouse in the Woods Pet Policy This 2-bedroom vacation rental in Chicago allows 2 dogs of any size for an additional fee of $95 per pet, per stay. Cats may also be allowed by request. Visit Website
    $205
    +$100 per pet
    Big dogs OK
    2 pets max
    Sleeps 5

    Pet-Friendly Apartment with In-Unit Laundry

    4.9 Chicago, IL
    Pet-Friendly Apartment with In-Unit Laundry Pet Policy This 1-bedroom apartment in Chicago allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. Please share the number and breed of your pets. Visit Website
    $166
    +$25 per pet
    10 kg max
    2 pets max
    Sleeps 8

    A Comfortable Stay While You Are Away

    4.7 Chicago, IL
    A Comfortable Stay While You Are Away Pet Policy This 3-bedroom house in Chicago allows 2 dogs under 20 lbs for an additional fee of $25 per pet, per stay. Sorry, no cats. Pets are not allowed on the furniture. Visit Website
    $247
    +$50 per pet
    Big dogs OK
    2 pets max
    Sleeps 4

    Stylish 2-Bedroom in Avondale Near Logan Square

    5.0 Chicago, IL
    Stylish 2-Bedroom in Avondale Near Logan Square Pet Policy This 2-bedroom apartment in Chicago allows 2 dogs of any size for an additional fee of $50 per pet, per stay. Sorry, no cats. Visit Website
    $287
    +$15/pet/night
    Big dogs OK
    1 pet max
    Sleeps 6

    3BR Spacious Home Away From Home

    4.9 Chicago, IL
    3BR Spacious Home Away From Home Pet Policy This 3-bedroom vacation rental in Chicago allows 1 dog of any size for an additional fee of $15 per night. Sorry, no cats. Visit Website
    $237
    +$20 per pet
    25 kg max
    2 pets max
    Sleeps 6

    Modern Apartment with Open Floor Plan

    4.8 Chicago, IL
    Modern Apartment with Open Floor Plan Pet Policy This 2-bedroom condo in Chicago allows 2 dogs under 50 lbs for an additional fee of $20 per pet, per stay. Sorry, no cats. Pets are not permitted on the furniture. Visit Website
    $174
    +$50 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 5

    Lyndale 1R

    5.0 Chicago, IL
    Lyndale 1R Pet Policy This 2-bedroom vacation rental in Chicago allows dogs of any size for an additional fee of $50 per pet, per stay. Cats are also welcome. Visit Website
    $90
    +$50 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 5

    Comfy Avondale Flat - Sleeps 4

    4.2 Chicago, IL
    Comfy Avondale Flat - Sleeps 4 Pet Policy This 1-bedroom apartment in Chicago allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request. Visit Website
    $421
    +$15/night pet fee
    Big dogs OK
    1 pet max
    Sleeps 2

    #1114q Osp B

    4.0 Chicago, IL
    #1114q Osp B Pet Policy This apartment in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Breed restrictions may apply. Visit Website
    Chicago, IL, US