
Pet-friendly holiday rentals in Downtown Chicago
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Downtown Chicago
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago pet-friendly home rentals
Pet-friendly house rentals

Home in Chicago
4.94 out of 5 average rating, 122 reviewsSpacious Full Home Near the Heart of Wrigleyville

Home in Chicago
4.96 out of 5 average rating, 160 reviewsChicago River House -Large private entire home

Home in Blue Island
4.81 out of 5 average rating, 188 reviewsWarm and comfortable inviting Suburban home !

Home in Bolingbrook
4.92 out of 5 average rating, 127 reviewsThe Sunshine Spot

Home in Riverdale
4.95 out of 5 average rating, 55 reviewsBeautiful , fully renovated

Home in Chicago Ridge
4.93 out of 5 average rating, 113 reviewsQuiet cul-de-sac with huge fenced in backyard

Home in Chicago
4.76 out of 5 average rating, 75 reviewsCheerful 2+ bedroom home w free parking

Home in Forest Park
4.91 out of 5 average rating, 106 reviewsAdorable house Madison Street w/ 2 car garage!
Pet-friendly home rentals with a pool

Apartment in Chicago
4.77 out of 5 average rating, 73 reviewsLevel ◆ Brand New Luxe One Bedroom

Apartment in Chicago
4.83 out of 5 average rating, 77 reviewsQuiet but in the Heart of City walk Everywhere

Apartment in Chicago
4.64 out of 5 average rating, 67 reviewsGold Coast Dream: Sleek Studio/Perfect City Vibes”

Apartment in Chicago
4.7 out of 5 average rating, 117 reviewsPlay in the Windy City and rest by the “606”

Apartment in Chicago
4.83 out of 5 average rating, 224 reviewsSpectacular Corner 2BR Penthouse in the Loop | Roo

Place to stay in River Forest
5 out of 5 average rating, 12 reviewsLong term rental-Delightful one bdrm pool house

Apartment in Chicago
4.9 out of 5 average rating, 67 reviewsDTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool

Apartment in Chicago
4.81 out of 5 average rating, 63 reviewsCozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Private, pet-friendly home rentals

Guest suite in Chicago
4.93 out of 5 average rating, 403 reviewsPeaceful Portage Park Apartment

Apartment in Chicago
5 out of 5 average rating, 16 reviewsBright and full of life!

Apartment in Westchester
4.96 out of 5 average rating, 28 reviewsShort Drive to Hospitals/Airports/Downtown Chicago

Condo in Chicago
4.92 out of 5 average rating, 221 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.

Apartment in Chicago
4.98 out of 5 average rating, 125 reviewsNewly-renovated historic home in Logan Square

Apartment in Chicago
4.76 out of 5 average rating, 72 reviewsArtsy Chicago Abode: Steps to Shops & Restaurants
Apartment in Chicago
4.92 out of 5 average rating, 251 reviewsSkylights, King Bed, 2 bedrooms

Townhouse in Chicago
4.98 out of 5 average rating, 64 reviews𓃥Wicker Cozy Corner w/Parking on site
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
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- House rentals Downtown Chicago
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- Hotel rentals Downtown Chicago
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