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
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Popular amenities for Downtown Chicago pet-friendly home rentals
Pet-friendly house rentals
Home in Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
7–14 Sep
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
26 Feb – 5 Mar
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
20–27 Jun
Home in North Park
4.96 out of 5 average rating, 126 reviewsChicago Riverhouse summer on our patio!
26 Jan – 2 Feb
Home in Chicago
4.81 out of 5 average rating, 196 reviewsSpacious Luxury Townhouse - Old Town
5–12 Dec
Home in Chicago
4.83 out of 5 average rating, 138 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
20–27 Jan
Home in Chicago
4.98 out of 5 average rating, 132 reviewsSouthwestern Penthouse TRES | Sleeps 12
15–22 Jan
Home in Avondale
4.93 out of 5 average rating, 209 reviewsLuxe 6BR House *Trendy Logan Square *Garage Access
21–28 Dec
Pet-friendly home rentals with a pool
Flat in Chicago
4.78 out of 5 average rating, 156 reviewsBeautiful Corner 2 Bedroom in the Loop | Roof Deck
5–12 Feb
Flat in Itasca
4.77 out of 5 average rating, 181 reviewsKing Bed at Chicago Northwest + PET Friendly
29 Oct – 5 Nov
Flat in Chicago
5.0 out of 5 average rating, 7 reviewsCozy studio near Michigan lake
9–16 Jul
Flat in Rosemont
5.0 out of 5 average rating, 14 reviewsRelaxing Standard Room l Free Airport Shuttle
28 Jun – 5 Jul
Flat in The Loop
4.86 out of 5 average rating, 7 reviewsSafe Downtown Penthouse Lake Views #1|Gym, Parking
7–14 Jun
Flat in Chicago
5.0 out of 5 average rating, 7 reviewsLuxury Designer Penthouse South |Pool| Gold Coast
19–26 Nov
Campsite in Midlothian
4.99 out of 5 average rating, 76 reviewsWaverly Woods Outpost: Private Glampsite w Theater
23–30 Oct
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
31 Aug – 7 Sep
Private, pet-friendly home rentals
Flat in Chicago
4.91 out of 5 average rating, 225 reviewsSkylights, King Bed, 2 bedrooms
18–25 Nov
Tiny home in Burr Ridge
4.92 out of 5 average rating, 240 reviewsLess is more! Pet friendly Tiny Home near Chicago!
29 Sep – 6 Oct
Flat in Forest Park
5.0 out of 5 average rating, 219 reviewsLike a Treehouse!
5–12 Sep
Guest suite in Chicago
4.84 out of 5 average rating, 200 reviewsVintage Suite Home Chicago by Sox/Park/Transit
17–24 Mar
Flat in Chicago
4.88 out of 5 average rating, 302 reviewsUnwind in the Garden of an elegant, Modern Home
13–20 Jan
Guest suite in Chicago
4.91 out of 5 average rating, 169 reviewsChicago Living: Your Home Away From Home
2–9 Mar
Flat in Chicago
4.88 out of 5 average rating, 188 reviewsComfort zone
6–13 Jan
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
25 Sep – 2 Oct
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
- Apartment rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with beach access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with pools Downtown Chicago
- Beachfront rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a firepit Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Waterfront rentals Downtown Chicago
- Pet-friendly rentals Milwaukee
- Pet-friendly rentals Chicago Loop
- 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