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, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
20–27 Jun
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
26 Feb – 5 Mar
Home in Chicago
4.96 out of 5 average rating, 126 reviewsChicago Riverhouse summer on our patio!
7–14 Sept
Home in Chicago
4.83 out of 5 average rating, 138 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
20–27 Jan
Home in Lincoln Park
4.81 out of 5 average rating, 196 reviewsSpacious Luxury Townhouse - Old Town
5–12 Dec
Home in Chicago
4.98 out of 5 average rating, 132 reviewsSouthwestern Penthouse TRES | Sleeps 12
15–22 Jan
Home in Chicago
4.82 out of 5 average rating, 122 reviewsBucktown Home W/ Free Garage Parking for 2 Cars!
24 Feb – 3 Mar
Home in Berwyn
5.0 out of 5 average rating, 75 reviewsRetro Modern Bungalow | free parking | pets ok
12–19 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 East Rogers Park
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
Campsite in Midlothian
4.99 out of 5 average rating, 76 reviewsWaverly Woods Outpost: Private Glampsite w Theater
23–30 Oct
Flat in Chicago
5.0 out of 5 average rating, 5 reviewsDtown Penthouse 3bd VIEWS+Parking +Gym
21–28 May
Flat in Magnificent Mile
5.0 out of 5 average rating, 6 reviewsLuxury Designer Penthouse South |Pool| Gold Coast
19–26 Nov
Yurt in Homewood
4.97 out of 5 average rating, 74 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
18–25 Jan
Private, pet-friendly home rentals
Flat in Chicago
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
5–12 Mar
Flat in Chicago
4.88 out of 5 average rating, 188 reviewsComfort zone
6–13 Jan
Flat in Chicago
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
14–21 Oct
Flat in Chicago
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
9–16 Feb
Guest suite in Wood Dale
4.9 out of 5 average rating, 427 reviewsThe Deer Suite
17–24 Oct
Guest suite in Chicago
4.94 out of 5 average rating, 124 reviewsComfortable & Cozy in Bridgeport
1–6 Jul
Flat in Chicago
4.91 out of 5 average rating, 225 reviewsSkylights, King Bed, 2 bedrooms
18–25 Nov
Flat in Forest Park
4.98 out of 5 average rating, 285 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
21–28 Sept
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
- Rentals with a hot tub Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Apartment rentals Chicago
- Hotel rentals Chicago
- Rentals with a cinema Chicago
- Beachfront rentals Chicago
- Guest house rentals Chicago
- Private suite rentals Chicago
- Fitness-friendly rentals Chicago
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- Loft rentals Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a sauna Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Monthly Rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
- Rentals with a firepit Chicago
- Rentals with outdoor seating Chicago
- Waterfront rentals Chicago
- Rentals with breakfast Chicago
- Mansion rentals Chicago
- Rentals with a patio Chicago
- Flat rentals Chicago
- Lakehouse rentals Chicago
- Boutique hotel rentals Chicago
- Townhouse rentals Chicago
- Villa rentals Chicago
- Cottage rentals Chicago
- Rentals with beach access Chicago
- Rentals with lake access Chicago
- Smoking-friendly rentals Chicago
- Rentals with a balcony Chicago
- Pet-friendly 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
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- Castle Rentals United States
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- Holiday Chalets United Kingdom
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