Pet-friendly holiday rentals in South Side

This wasn’t really supposed to be a “fun” trip. I unfortunately had to put my mom into assisted living, but found this Airbnb close to her home. My 2 boys came with me (10 & 13) and if it wasn’t for the fun accommodations in this house, they wouldn’t have had the awesome time they did. It was a fantastic distraction, and the house felt like a home. We loved the updated bathrooms, the modern look and feel, and don’t forget the basement! We spent lots of time down there playing putt putt and arcade games. My son even hooked up his X-Box and played (which he ended up leaving behind on accident, and the host Marc actually drove it to my moms to drop it off - A SAINT!) We will likely be back at least every couple months to check on my mom and will book here from now on!

This was a fantastic stay! The space was beautiful, spacious, clean, and well located. Definitely a great option if you're in the area and need a larger space.

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.

Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

We enjoyed our stay. Clean, nice house, and in a location convenient to everything we wanted to do. Host was very responsive when we had questions. We loved being so close to the train. Great restaurants around, and also a convenience store and Family Dollar right around the corner for anything you need!

Very nice place very big only things is there was only one bathroom, With a lot of people that can get pretty cramped , Adam was very responsive and understanding!

I enjoyed staying at Rich's place. If you want to fish, the calumet river Greenway isn't far, and it's easy access to I-57 N/S too.

The house is very beautiful. My family and I loved the place and how spacious it is.

Overall great for our stay, Fairly close to a lot of things.

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.

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.

Excellent place to stay, easy access to highway, quick ride to downtown

Cool building in a great location. Everything was quite nice. Really liked the layout which provides enough space for two couples to have privacy.

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!

⭐️⭐️⭐️⭐️⭐️ 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!✨

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.

Great stay, Both host were very great communicators, helped out with ANY thing. This house was BIG too big for my party very spacious nice interior, nice decor. If I was to visit Chicago, IL again this would be my stay, Thanks to the host for making my trip comfortable and fun.

Thank you for a wonderful stay! You were very accommodating.

If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.

Daniel’s place was very cozy and just what we needed for me to go into the city for a few days. The garage parking was nice to have to not have to fret about dealing with street parking. A gigantic plus is the fenced in backyard that my girl loved, and being pet friendly in general, my furbaby is my everything and I never go anywhere without her! 🩷

Loved being just a couple blocks from the Western Pink Line station and bus stops both north-south and east-west.

“This place was an absolute gem! The house was spotless, stylish, and exactly as described. The location was perfect—close to everything but still peaceful at night. I’d definitely stay here again and highly recommend it to anyone visiting the area!”

This is my second (maybe 3rd?) stay at one of Jordan & Jeremy's properties and the experience is consistently pleasant. Listing is accurate, place is cozy and clean. I wish all AirBnBs were this consistent!

Our stay was perfect and I would definitely stay again! We hosted a small dinner for my mom’s memorial service and they were very accommodating. There was plenty of space for everyone and the location was great. All the amenities were top notch and the decor was amazing. We felt right at home and I’ve referred people to stay. Thank you so much for hosting us. 10 stars!!!