Pet-friendly holiday rentals in Chicago
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in 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 Chicago pet-friendly home rentals
Pet-friendly house rentals
Home in Forest Park
4.91 out of 5 average rating, 224 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Home in Chicago
4.95 out of 5 average rating, 129 reviewsChicago Riverhouse summer on our patio!
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Home in Highland Park
4.91 out of 5 average rating, 110 reviewsRejuvenate and Relax in the North Shore
Home in Chicago
4.81 out of 5 average rating, 197 reviewsSpacious Luxury Townhouse - Old Town
Home in Bolingbrook
4.92 out of 5 average rating, 99 reviewsThe Sunshine Spot
Home in Chicago
4.98 out of 5 average rating, 132 reviewsSouthwestern Penthouse TRES | Sleeps 12
Home in Chicago
4.82 out of 5 average rating, 123 reviewsBucktown Home W/ Free Garage Parking for 2 Cars!
Pet-friendly home rentals with a pool
Flat in Chicago
4.86 out of 5 average rating, 190 reviewsSpectacular Corner 2BR Penthouse in the Loop | Roo
Flat in Itasca
4.76 out of 5 average rating, 189 reviewsKing Bed at Chicago Northwest + PET Friendly
Flat in Chicago
4.87 out of 5 average rating, 110 reviewsLevel ◆ Two Bedroom Deluxe Corner Suite + Balcony
Flat in Chicago
5.0 out of 5 average rating, 9 reviewsCozy studio near Michigan lake
Flat in Chicago
4.91 out of 5 average rating, 33 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Chicago
4.89 out of 5 average rating, 9 reviewsDowntown Penthouse Lake Views #1|Gym, Parking+Pool
Flat in Chicago
4.88 out of 5 average rating, 8 reviewsLuxury Designer Penthouse South |Pool| Gold Coast
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Private, pet-friendly home rentals
Guest suite in Chicago
4.94 out of 5 average rating, 127 reviewsComfortable & Cozy in Bridgeport
Flat in Chicago
4.89 out of 5 average rating, 341 reviewsSunny Logan Square Artists' home
Flat in Chicago
4.88 out of 5 average rating, 190 reviewsComfort zone
Flat in Chicago
4.89 out of 5 average rating, 177 reviewsHistoric Chicago neighborhood flat
Flat in Oak Park
4.92 out of 5 average rating, 106 reviewsLovely, spacious 2bd, 1bath home w/free parking
Flat in Chicago
4.83 out of 5 average rating, 481 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Flat in Chicago
4.91 out of 5 average rating, 226 reviewsSkylights, King Bed, 2 bedrooms
Guest suite in Chicago
4.84 out of 5 average rating, 202 reviewsVintage Suite Home Chicago by Sox/Park/Transit
Quick stats about holiday rentals that are pet-friendly in Chicago
Total rentals
3.3K properties
Wifi availability
3.2K properties include access to wifi
Rentals with dedicated workspaces
2.3K properties have a dedicated workspace
Rentals with a pool
700 properties have a pool
Family-friendly rentals
1.7K properties are a good fit for families
Total number of reviews
128K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Fitness-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an EV charger Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Flat rentals Chicago
- Rentals with a sauna Chicago
- Hotel rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Beachfront rentals Chicago
- Townhouse rentals Chicago
- Rentals with beach access Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Boutique hotel rentals Chicago
- Guest house rentals Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Private suite rentals Chicago
- Monthly Rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a patio Chicago
- Mansion rentals Chicago
- Waterfront rentals Chicago
- Smoking-friendly rentals Chicago
- Lakehouse rentals Chicago
- Family-friendly rentals Chicago
- Pet-friendly rentals Downtown Chicago
- Pet-friendly rentals Milwaukee
- Pet-friendly rentals Lake Geneva
- Pet-friendly rentals Illinois
- Pet-friendly rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom