Pet-friendly holiday rentals in West Side

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for West Side pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Chicago
4.94 out of 5 average rating, 124 reviews

Spacious Full Home Near the Heart of Wrigleyville

JessicaRating, 5 stars1 month ago
We had an amazing stay at Dustin’s place! We had a group of 9 ladies who fit perfectly with plenty of cozy beds and linens. The location was very walkable and we felt safe. We walked over to Barcocina Lakeview on Friday, and then jumped on the train to River North on Saturday to celebrate St. Patrick’s Day. We had a couple of questions during our visit, and Dustin was speedy on the replies! Everyone in the group said the experience was 10 out of 10. We hope to visit again.
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 168 reviews

Chicago River House -Glowing Sofa Oasis

LuaRating, 5 stars4 days ago
We had our mini wedding at this home and it was perfect for us! Everything was great and the host was very communicative and understanding.
Superhost
Home in Chicago
4.86 out of 5 average rating, 99 reviews

Casa PLZN Location | Entire Home | Garage Parking

CecilioRating, 5 stars3 weeks ago
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.
Guest favourite
Home in Naperville
4.87 out of 5 average rating, 130 reviews

Home away from home

JordanRating, 5 stars1 month ago
We couldn’t have asked for a better home for our Spring Break. We last minute booked this home, and checked in 45 later but you would have never known by how welcoming Vytauta made it. Beds were very comfortable, backyard was great, we felt right at home.
Superhost
Home in Blue Island
4.81 out of 5 average rating, 193 reviews

Warm and comfortable inviting Suburban home !

MarcusRating, 5 stars3 days ago
Always a pleasure staying with at Rich’s place
Superhost
Home in Bolingbrook
4.92 out of 5 average rating, 130 reviews

The Sunshine Spot

SavahannahRating, 5 stars2 weeks ago
We stayed for a week. The house was spacious and clean, and the neighborhood felt very safe. It was close to the mall and any store you'd ever need. Richard was very responsive and helpful! Washer & dryer were great to have for a longer stay. Wifi and smart tv were great. Also was glad there was even a lead in the backyard for our dog!
Top guest favourite
Home in Chicago Ridge
4.93 out of 5 average rating, 123 reviews

Quiet cul-de-sac with huge fenced in backyard

MichaelRating, 5 stars3 weeks ago
Absolutely loved staying here. Tom was an awesome host. He has very detailed instructions throughout the house for everything from connecting to the WiFi to how the individual tvs work. The couch in the living room is stupid comfortable and the master bedroom was cool and dark. 10/10 would stay here again
Superhost
Home in Wood Dale
4.76 out of 5 average rating, 160 reviews

Excellent Location for Vacation or Business Stays.

JamesRating, 5 stars3 months ago
This was our second stay at Rita’s and we found it very accommodating and great of an experience as our last visit. The neighborhood is in a great location and it is cozy and quiet. The property was extremely clean. We would be happy with staying here again in the future.

Pet-friendly home rentals with a pool

Superhost
Flat in Chicago
4.77 out of 5 average rating, 73 reviews

Level ◆ Brand New Luxe One Bedroom

GregRating, 5 stars2 months ago
What isn’t to like about this place? Amazing building, incredible views (from the unit I was in), beautiful unit, great amenities, perfect location, friendly staff. I will be staying here whenever I visit Chicago in the future.
Guest favourite
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars3 months ago
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.
Guest favourite
Flat in Chicago
4.9 out of 5 average rating, 70 reviews

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool

CarmillaRating, 5 stars3 weeks ago
This is a nice place to stay. We enjoyed the location and amenities.
Superhost
Flat in Chicago
4.81 out of 5 average rating, 64 reviews

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

JosephRating, 5 stars3 weeks ago
This place is a great location for almost anything one would like to do in Chicago. Close to train lines, plenty of surrounding restaurants and grocery stores, and parking was a breeze. Also Kevin was a wonderful host and this apartment was exactly what I needed for the stay.
Guest favourite
Flat in Chicago
4.82 out of 5 average rating, 22 reviews

Modern unit in Bridgeport-Chicago

MackenaRating, 5 stars1 week ago
Conveniently located and just a cute little spot. Perfect for a resting place after being in the city all day.
Guest favourite
Flat in Chicago
4.94 out of 5 average rating, 53 reviews

Chicago’s Best PH! Views Like No Other!|The Arc

BriannaRating, 5 stars1 month ago
I stayed here for a bachelorette trip and it was absolutely iconic. One of the only trips I’ve been on where I was perfectly content to stay inside all day. The view was unbelievable in all weather, incredibly spacious, and close to everything we needed. Located on the same block as a cvs and grocery store for quick access to anything we forgot/food we wanted along with a sweet cafe right off the lobby. Charlie was very responsive via text but we had no issues. 10/10, would absolutely stay again.
Superhost
Flat in Chicago
4.72 out of 5 average rating, 155 reviews

Sentral Studio Apt in South Loop Chicago

TobiasRating, 5 stars1 month ago
This is probably the most value-for-money place you will find in the area. Spatious, clean and modern studio apartment, close to the park and downtown, great view on the skyline, and all for a fraction of the costs of nearby hotels.
Superhost
Flat in Chicago
4.84 out of 5 average rating, 31 reviews

Luxury Designer Penthouse North |Pool| Gold Coast

KarenRating, 5 stars4 days ago
Great location, beautiful view, and very nice and comfortable condo!

Private, pet-friendly home rentals

Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 412 reviews

Peaceful Portage Park Apartment

DruRating, 5 stars2 weeks ago
I got what I paid for and was satisfied with my choice of this Airbnb. I will highly consider staying here again next time I come to Chicago!
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 230 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

MartinRating, 5 stars2 weeks ago
This place was fantastic. Exactly what I thought it was going to be from the description and pictures. Kaye was super responsive and helpful when we needed info or to borrow something. She is a super host indeed. Will definitely be back!
Top guest favourite
Flat in Chicago
4.98 out of 5 average rating, 130 reviews

Newly-renovated historic home in Logan Square

LynnRating, 5 stars2 weeks ago
I had a wonder stay at this charming flat in Chicago. Danny's home is a beautiful historical building full of character, and the interior was clean, comfortable and well maintained. One of my favorite parts was the cozy backyard-such a peaceful spot to relax on a warm morning or unwind in the evening. You're right in the center of activity, but have plenty of privacy. Danny was friendly, responsive and made everything super easy. I'd definitely stay here again and highly recommend it to anyone, and their dog, visiting Chicago!
Superhost
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars1 month ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
Guest favourite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 337 reviews

a SIMPLE place

KaitlinRating, 5 starstoday
This is the 2nd time I've stayed here, and it is always exactly what I need. The space is great, the neighborhood is safe, and there's a Lou Malnatis and Portillos within a 15 min drive. Will definitely stay again!
Guest favourite
Flat in Chicago
4.85 out of 5 average rating, 171 reviews

Oasis Collection's Mid-Century 3 Bd Wicker Park.

BeckieRating, 5 stars3 weeks ago
This is a very clean and comfortable unit. The beds are very comfy, the comforts are wonderfully soft. Basic toiletries and kitchen essentials are provided. The location is excellent for us, as we have young grandchildren and a dog, both enjoyed wicker park. Many restaurants are close enough for walking.
Superhost
Flat in Chicago
4.84 out of 5 average rating, 105 reviews

Personal Parking, In-Unit Laundry & King Bed

NufileRating, 5 stars3 weeks ago
What you pay is what you get. We didn’t come to Chicago to cook, so kitchen wasn’t an essential part of our amenities. Aside from that, it’s the best bang for our buck. The hosts are lovely people and I would come back to this place again! Loved it
Guest favourite
Flat in Chicago
4.89 out of 5 average rating, 173 reviews

Private 2 Bedroom Retreat

JeffreyRating, 5 stars1 month ago
Great stay for two months while we shopped for an apartment in Chicago. The location is fantastic—walkable to tons of restaurants, bars and the L. And Wendi's apartment was fully stocked, from kitchen to bathroom, with the things we needed to feel at home for two months.

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