Pet-friendly holiday rentals in Oak Park

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Oak Park pet-friendly home rentals

Pet-friendly house rentals

Top guest favourite
Home in Uptown
4.9 out of 5 average rating, 367 reviews

Private 3rd Floor Apartment

RickRating, 5 stars1 month ago
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.
Guest favourite
Home in Glen Ellyn
4.91 out of 5 average rating, 154 reviews

Home in Glen Ellyn

KatharynRating, 5 stars2 weeks ago
The home was beautiful. And I love the master bedroom I felt like a queen walking into the room private bathroom. Big backyard. Everything was fabulous and next time I go back I will stay there again if available.
Guest favourite
Home in Avondale
4.94 out of 5 average rating, 148 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

niratiRating, 5 stars3 weeks ago
Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!
Superhost
Home in Bolingbrook
4.93 out of 5 average rating, 134 reviews

The Sunshine Spot

AlRating, 5 stars2 weeks ago
House is centrally located . Clean. Host was responsive. 100% recommend this property !
Superhost
Home in Naperville
4.85 out of 5 average rating, 126 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

MicahRating, 5 stars2 weeks ago
Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.
Guest favourite
Home in Chicago Ridge
4.91 out of 5 average rating, 143 reviews

Quiet cul-de-sac with huge fenced in backyard

MeganRating, 5 stars4 days ago
Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.
Top guest favourite
Home in Portage Park
4.97 out of 5 average rating, 117 reviews

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

ErikaRating, 5 stars1 week ago
The house is very beautiful. My family and I loved the place and how spacious it is.
Superhost
Home in Wood Dale
4.75 out of 5 average rating, 167 reviews

Excellent Location for Vacation or Business Stays.

SabrinaRating, 5 stars1 week ago
Rita’s place was perfect for our weekend stay!It had plenty of space, was easily walkable to the train station and restaurants, and had everything we needed. Rita was communicative and super kind. We would definitely recommend this stay for others.

Pet-friendly home rentals with a pool

Guest favourite
Serviced apartment in The Loop
4.95 out of 5 average rating, 43 reviews

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

QuaneshaRating, 5 stars1 week ago
Overall great for our stay, Fairly close to a lot of things.
Guest favourite
Flat in Magnificent Mile
5 out of 5 average rating, 8 reviews

Luxury Designer Penthouse NW | Pool | Gold Coast

ReginaRating, 5 stars2 weeks ago
Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.
Superhost
Townhouse in Forest Park
5 out of 5 average rating, 5 reviews

Forest Park Oasis - Dog Friendly - Parks - the "L"

MeghanRating, 5 stars1 week ago
Excellent place to stay, easy access to highway, quick ride to downtown
Guest favourite
Flat in The Loop
4.83 out of 5 average rating, 12 reviews

South Loop | Rooftop With In & Out Parking | 1

DayanaRating, 5 stars4 days ago
We had a wonderful stay in Chicago with our infant and toddler! The check-in process was smooth and easy, which made settling in stress-free. The apartment was clean and cozy, with fresh sheets, a spotless bathroom and bedroom. The kitchen was fully stocked with all the essential utensils made it convenient to prepare breakfast for the kids. One big plus was the parking, the detailed video provided made it super easy to find the exact location without any confusion. The location of the apartment was fantastic within walking distance to Willis Tower and surrounded by great restaurants. It was also just a short 15 mins drive to major attractions like the Shedd Aquarium, Adler Planetarium, and Navy Pier. Everything we needed was already available in the room, we didn’t have to call out or ask for anything during our stay. Overall, a comfortable and convenient stay for families traveling with little ones. Highly recommended!
Superhost
Flat in Logan Square
4.79 out of 5 average rating, 71 reviews

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

NicholeRating, 5 stars2 weeks ago
This was a perfect stay for an amazing weekend getaway and Festival experience. The area was walkable and had several great options for food and bev. Free street parking directly in front of the property, secure garden level access, and all the instructions and guidance were well laid out. Additionally, they had a guidebook that was well put together and everything was cohesive and exactly as pictured and described in the app. John was very responsive, friendly, and he and his family provided a perfectly appointed environment for our getaway… And their dog, Star 🐶 was such an angel! We had a great time, thank you!
Superhost
Serviced apartment in River North
4.73 out of 5 average rating, 278 reviews

Level ◆ New Luxe Two Bedroom Corner Suite

Don Rating, 5 stars1 month ago
The place was spectacular. The views are breathtaking. My family and I loved the place.
Superhost
Flat in Bridgeport
4.73 out of 5 average rating, 33 reviews

Modern unit in Bridgeport-Chicago

AnaliciaRating, 5 stars1 day ago
⭐️⭐️⭐️⭐️⭐️ An unforgettable stay in the heart of the city! This Airbnb was absolutely amazing! The location couldn’t have been more perfect right in the middle of everything, with easy access to restaurants, shops, and public transportation. The space was spotless, beautifully decorated, and felt like a true home away from home. Our host went above and beyond to make sure we had everything we needed. Their hospitality, local tips, and quick communication made our stay even more enjoyable. You can tell they genuinely care about their guests’ experience. If you’re looking for a comfortable, stylish place to stay with an incredible host in Chicago, look no further. We’re already planning our next trip back!✨
Guest favourite
Flat in The Loop
4.86 out of 5 average rating, 7 reviews

Luxury 3 Bed w/ Gym, Pool, Parking, Game Rm & More

ShuangRating, 5 stars1 week ago
Great value for a work trip! Easy to find, convenient amenities, and Patty was very proactive with a clear, easy check-in. Would recommend for a small group.

Private, pet-friendly home rentals

Guest favourite
Townhouse in Oak Park
5 out of 5 average rating, 24 reviews

A Pleasant Stay in Oak Park

BrianRating, 5 stars1 week ago
Very clean well appointed space. An older townhome, the unit is fully stocked with everything one would need, and parking behind the unit was extremely convenient. Jay was very responsive and helpful. Close walk to train station and restaurants, on a quiet block, with everything one might need.
Guest favourite
Home in Austin
4.93 out of 5 average rating, 15 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

Danielle GRating, 5 stars4 days ago
Rameez was an amazing host! Making the experience even more enjoyable with his quick responses & fast accommodations. The home is more spacious than it looks in the photos and it truly exceeded my expectations. I had a great stay for my birthday!
Superhost
Flat in Oak Park
4.71 out of 5 average rating, 41 reviews

1 bedroom apartment in lovely Victorian house

IvanRating, 5 stars4 weeks ago
Beautiful home, has quiet stay and enjoy how close it was to downtown. Truly recommend.
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 23 reviews

Big house in the BEST Location!

JodiRating, 5 stars3 days ago
The house is lovely! Better than the pictures, just as all of the reviews say. The showers are incredible. The master bathroom is a dream. We had everything we needed & more. We don’t have a single complaint. We definitely plan on booking here again.
Superhost
Flat in Berwyn
4.81 out of 5 average rating, 53 reviews

Private Garden APT/ Cozy/Warm

CalebRating, 5 stars6 days ago
Quiet and friendly neighborhood. Very walkable. Place had everything I needed for the stay. Will definitely return if I’m ever in the area again.
Top guest favourite
Home in Oak Park
5 out of 5 average rating, 42 reviews

Oak Park - Wine House!

AltheaRating, 5 stars2 weeks ago
Excellent place to stay if you want to be in a “suburban-feel” of the city: you’re in a neighborhood that is steps away from a “main street” walkable area with shops. The two parking spots are very convenient and the main floor is so thoughtfully decorated and furnished. Everything is 5 stars, just want to make a few notes: be wary of the stairs as they can be a little slippery if you don’t have any grippy socks or slippers and there is only one full bathroom so you’ll have to share this with the other guests, also there are blinds but no blackout curtains so you’ll wake up with the sun. The neighbors are very nice, but if the kids are out and about you will hear them clearly. Would 100% book again!
Top guest favourite
Flat in Forest Park
4.92 out of 5 average rating, 77 reviews

Gorgeous Penthouse with Parking in Heart of Forest Park

JosephineRating, 5 stars1 week ago
Linda was a truly gracious hostess and immediately responded any time we had a question. I can highly recommend her beautiful home!
Superhost
Home in Oak Park
4.75 out of 5 average rating, 24 reviews

Private Suite Quiet Safe OakPark

CindiaRating, 5 stars2 months ago
It’s a nice, quiet neighborhood. Definitely felt safe. The space was clean and comfortable. Perfect for a one night stay in Chicago.

Quick stats about holiday rentals that are pet-friendly in Oak Park

  • Total rentals

    70 properties

  • Nightly prices starting at

    $90 SGD before taxes and fees

  • Total number of reviews

    3.9K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi

Destinations to explore

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