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 Berwyn
4.91 out of 5 average rating, 262 reviewsPrivate apartment with retro vibe
Home in Forest Park
4.9 out of 5 average rating, 227 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Home in North Park
4.95 out of 5 average rating, 133 reviewsChicago Riverhouse with private patio!
Home in Chicago
4.9 out of 5 average rating, 339 reviewsPrivate 3rd Floor Apartment
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Home in Chicago
4.81 out of 5 average rating, 200 reviewsSpacious Luxury Townhouse - Old Town
Home in Avondale
4.93 out of 5 average rating, 212 reviewsLuxe 6BR House *Trendy Logan Square *Garage Access
Home in Bolingbrook
4.92 out of 5 average rating, 103 reviewsThe Sunshine Spot
Pet-friendly home rentals with a pool
Apartment in Chicago
4.78 out of 5 average rating, 163 reviewsBeautiful Corner 2 Bedroom in the Loop | Roof Deck
Apartment in Itasca
4.73 out of 5 average rating, 207 reviewsKing Bed at Chicago Northwest + PET Friendly
Apartment in Rosemont
4.94 out of 5 average rating, 32 reviewsRelaxing Standard Room l Free Airport Shuttle
Apartment in Chicago
5.0 out of 5 average rating, 10 reviewsCozy studio near Michigan lake
Apartment in The Loop
4.92 out of 5 average rating, 13 reviewsDowntown Penthouse Lake Views #1|Gym, Parking+Pool
Apartment in Magnificent Mile
4.91 out of 5 average rating, 11 reviewsLuxury Designer Penthouse South |Pool| Gold Coast
Apartment in West Town
4.95 out of 5 average rating, 43 reviewsCozy 2 Bed Apt in Wicker Park East w/ Free Parking
Campsite in Midlothian
4.99 out of 5 average rating, 76 reviewsWaverly Woods Outpost: Private Glampsite w Theater
Private, pet-friendly home rentals
Guest suite in Chicago
4.9 out of 5 average rating, 171 reviewsChicago Living: Your Home Away From Home
Apartment in Chicago
4.88 out of 5 average rating, 151 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Apartment in Chicago
4.83 out of 5 average rating, 485 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.93 out of 5 average rating, 115 reviewsLuxurious - 10 Minutes to Downtown Chicago - Cozy
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.87 out of 5 average rating, 307 reviewsUnwind in the Garden of an elegant, Modern Home
Guest suite in Skokie
4.87 out of 5 average rating, 152 reviewsAdorable studio style unit - Self check in ⚡️
Apartment in Chicago
4.88 out of 5 average rating, 193 reviewsComfort zone
Destinations to explore
- 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
- Chicago Holiday rentals
- Pet-friendly rentals Chicago
- Rentals with breakfast Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with lake access Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Waterfront rentals Downtown Chicago
- House rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Hotel rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Condo rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with pools 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