
Pet-friendly vacation rentals in West Side
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Top-rated pet-friendly home rentals in West Side
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Popular amenities for West Side pet-friendly home rentals
Pet-friendly house rentals

Spacious Full Home Near the Heart of Wrigleyville
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.

Chicago River House -BBQ Oasis now open!
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.

Casa PLZN Location | Entire Home | Garage Parking
Great place! I’ll definitely be coming back! The beds are amazing!

Home away from home
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.

Warm and comfortable inviting Suburban home !
very nice and responsive house great peaceful calm area just a little bit far from the city with traffic otherwise wonderful stay, plan to book again !

The Sunshine Spot
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!

Quiet cul-de-sac with huge fenced in backyard
Tom and his dog Bear... were great!! Beautiful home and great area. A lot of places that we wanted to go to were close by will definitely come again. Thank for having such a welcoming home.

Excellent Location for Vacation or Business Stays.
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

Level ◆ Brand New Luxe One Bedroom
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.

Quiet but in the Heart of City walk Everywhere
This place was incredible. My kids and I loved staying here. My young daughter had asked to stay in a "fancy hotel" on our trip, and this blew her mind with the views over the city, how nice the space was, and the pool and hot tub that we pretty much had to ourselves every evening. The kitchen had the things we needed to make our own meals. And we were within easy reach of every place we wanted to go. The included parking spot really took things over the top to make this a great deal and an amazing stay for our family.

Stylish Corner 2 Bedroom in the Heart of Chicago |
Fantastic location, felt incredibly safe, and was exactly as described. Great space and made for the perfect spot for our family during our stay in Chicago. Would absolutely return.

Long term rental-Delightful one bdrm pool house
Definitely a great stay! October 1st and we were swimming! Decor is amazing! Tv was easy to figure out and had lots of options. We had a busy day before and after our stay so we used Michael’s pool house as a relaxing stay in between and it was perfect

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
This is a nice place to stay. We enjoyed the location and amenities.

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

Modern unit in Bridgeport-Chicago
Great place! Came to Chicago for a conference and the place was only a 12 minute drive from the event center. I was worried about the area being unsafe, but the area was super nice! Very close to Chinatown too!

Luxury Designer Penthouse North |Pool| Gold Coast
Great location, beautiful view, and very nice and comfortable condo!
Private, pet-friendly home rentals

Peaceful Portage Park Apartment
Beautiful place to stay. Beautiful decor. Host very friendly and responsive. We had a baby with us and she had lots of baby items for us. We had street parking in front of home. 🏡

Cozy 1bdr Rogers Park, Loyola, Northwestern.
Love this place! It’s peaceful, walkable, plenty of things to do in the area and close to the Lake. Will definitely be back to stay here and visit family. Thanks Kaye, for always being responsive and helpful.

Newly-renovated historic home in Logan Square
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!

The Country Life! Entire House.
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.

a SIMPLE place
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!

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

Personal Parking, In-Unit Laundry & King Bed
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

Private 2 Bedroom Retreat
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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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Six Flags Great America
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Museum of Science and Industry
- The Field Museum
- Wicker Park
- Chicago History Museum
- Willis Tower
- Flossmoor Golf Club
- Brookfield Zoo
- Lincoln Park
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
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