
Pet-friendly vacation rentals in South Side
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Top-rated pet-friendly home rentals in South Side
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Popular amenities for South 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 -Glowing Sofa Oasis
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 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.

Warm and comfortable inviting Suburban home !
Always a pleasure staying with at Rich’s place

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.

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
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

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.

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.

Munster hide away
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.

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.

Your favorite vacation spot
A nice quiet calm getaway perfect for friends or family

Modern unit in Bridgeport-Chicago
Conveniently located and just a cute little spot. Perfect for a resting place after being in the city all day.
Private, pet-friendly home rentals

Peaceful Portage Park Apartment
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!

Short Drive to Hospitals/Airports/Downtown Chicago
The place was newly remodeled, very clean and organized. Everything in the apartment was well stocked and very livable, including Roku access to open your own subscriptions Hulu, Netflix, etc. Please be aware that the location is a basement with a relatively steep flight of stairs, with safety lips on the edges.

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!

Townhome Near Munster/Hospital/BP Refinery
The house was very clean and comfortable. Great location and safe neighborhood. We loved having a garage! The hosts were very attentive and we will be back.

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.

𓃥Wicker Cozy Corner w/Parking on site
Incredible stay! Hien was so friendly and responsive, the unit was beautiful and felt more spacious in person than in the photos! Lovely spot in the neighborhood, quiet street and amazing food and things to do nearby. Thanks so much Hien!

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
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- Six Flags Great America
- Museum of Science and Industry
- Chicago History Museum
- Lincoln Park Zoo
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Willis Tower
- Skokie Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Odyssey Fun World
- Flossmoor Golf Club
- Moraine Hills State Park
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