Kid-friendly vacation rentals in South Side

Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!

The hosts’ of this property were great and accommodating. They catered to our altered schedule and compromised on a request of ours. We will definitely stay here again.

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!

Caryl was extremely helpful with a check in process and she introduced us the property as well as surrounding local attractions. We felt the place was warm and very spacious for our group and we had a pleasant stay.

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.

My family and I had a great stay at Bel’s powder blue house. The house matched the pictures and description posted on the website, and was very clean and cozy inside. Bel’s communication was very effective throughout the entire experience, I will definitely be booking with him again in the future!

Absolutely fantastic stay. The house was clean, comfortable, and exactly as described—if not better. Every amenity we needed was thoughtfully provided, from linens and toiletries to kitchen essentials and beyond. The space was beautifully maintained and made us feel right at home. The host was truly exceptional—communicative, friendly, and clearly committed to providing a great experience. Check-in was seamless, and they were always available if we had any questions. I would not hesitate to stay here again. This property easily stands out among other options in the area. Highly recommend.

Absolutely stellar stay! Kymi’s Airbnb in Chicago was everything we hoped for and more during our time at ASCO. The home was beautifully decorated, exceptionally comfortable, and stocked with everything we needed. My family felt incredibly safe and at ease the entire time. Kymi herself was a dream host—warm, responsive, and genuinely hospitable. She graciously allowed us to extend our stay and have a late checkout, all without hesitation or hassle. Her kindness and attentiveness made the experience even more special. I highly encourage anyone visiting Chicago to stay at her amazing home—you won’t regret it!

Great stay, quiet neighborhood and good location. Would rent again!

Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I

Great apartment for a family stay. We visited Chicago for the 1st time and loved that the apartment was only 15 mins from the downtown core. Lots of room, very spacious, decorated like an art gallery. Tons of kitchen supplies, coffee, etc to make the stay extra comfortable. The apartment is on the 3rd floor so going up and down with small kids is a pain but it was worth it. Overall wonderful stay, would highly recommend!

5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!

Really enjoyed our stay. Great transport links in and out of the city, being close to two train stations, but out the way enough to enjoy a quieter and more local perspective on Chicago. Easy to access, clear instructions and the host was fantastic. Well presented and clean within, as well as being far bigger than expected! Nice little touches inside too, such as plenty of coffee, a bottle of red wine and pasta bolognaise if we chose to stay in. Overall, really enjoyed our stay and would absolutely recommend.

Kendal is a superhost. The apartment is as described. Enjoyed staying at this apartment. Very near to supermarkets, McCormick convention centre and public transport. Highly recommend.

The only issue was finding the location in the beginning, BUT their response time was extremely quick and they made sure they stayed on the phone with me until i found the address. They walked me through the entire neighborhood to get there. The area was walkable, and safe. Everything was clean and comfortable. I truly fell in love with the view of the apartment and the blue couch! The host did absolutely amazing. I paid for the garage parking which was the best decision i ever made! Safe, and not having to worry about daily parking findings. I will be back in august and i WILL be booking this apartment again!

Enjoyed staying here ! Would definitely come back again ! I enjoyed my morning runs to the lake, beautiful scenery. We mainly used Lyft during our stay and most were very affordable. The gym is close by walking distance in my opinion.

Zirrell was a wonderful host. She always responded and her instructions were very thorough. She was also very understanding when our flight got delayed and we checked in later than expected. The apartment was clean and looked just like the pictures. It was a wonderful stay!

Luke was a responsive, helpful, and friendly host. Stones Throw is a great location for access to the University of Chicago, and it’s a short walk to the Metra for trips downtown. We really enjoyed our stay here, and the highlight was Luke’s invitation to participate in the rooftop honey harvest!

Great location and responsive host. The amenities in the place are great and the bed is amazingly comfy. The airbnb was a bit dusty everywhere (the bottoms of our feet were black after walking around barefoot), but that seems par for the course for basement apartments that just hang on to dust.

747 Lofts was our Knight in Shinning Armor! We had to relocate from a nasty ABnB & found this diamond! Was great location, very clean, comfy, & everything worked as it should. Shower & kitchen was better than normal w/higher end/spa feel. Linens were nice & plush, too. Building & area was safe & clean. Love the theme of 747 Lofts! We’ll definitely stay here again when in Chicago!👍👍

The time spent here was wonderful. This place has everything you need to feel at home away from home. Everything was clean and comfortable. The area was also really nice with tons of food and drinks within walking distance. The blue line is a short walk away and the busses run on the corner. I would definitely stay here again when coming back to Chicago.

Susan’s home was comfortable, clean, well-equipped, and aesthetically pleasing. The bed I slept in was one of the most comfortable of my entire life—I prefer a soft mattress. As far as location goes, the street was quiet, good for walking our dog, and close enough to public transport. Plenty of buses were available. We used street parking for our car and never had problems with finding a close spot to the house whenever we did take the car out. We enjoyed the stay greatly and will stay again. Thank you, Susan!

My friends and I enjoyed our time at Kai's Airbnb. She was very responsive and provided clear information. I requested a new clothing iron and it was quickly brought us, it was nice to easily get in contact with her and her ability to solve problems fast. All the necessities were in the home as far as plentiful towels, toilet paper, blankets, nice pillows, tv's and great wifi, etc. All in all, I'd stay here again! It's not too far from the city and the neighborhood is quiet.

We stayed at Michelle's place for a long weekend girls trip. The building was secure, quiet and clean. We enjoyed the shared pool, deck, and lounge spaces. I appreciated the secure parking for our vehicle, this was a great bonus. Michelle was easy to communicate with and always prompt to respond. I would recommend Michelle's place to anyone visiting Chicago & the surrounding area.