Kid-friendly holiday 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!

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.

We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.

This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!

My family and I enjoyed staying here. I was born and raised in Chicago just 4 blocks from this Airbnb! It was such a great experience to be back in my old neighborhood. Olusesan is a phenomenal host! I highly recommend this place.

Kb's place was great for our holiday weekend in Chicago. The smart home was clean, comfortable, and welcoming. I would definitely book again!

The home was cozy and super convenient for what we needed. The backyard was so nice to get some outside time with the kids and we walked to the park up the street a couple of times. The kitchen had everything we needed. Melissa was very helpful in sharing what to know before getting there and a printed manual of facts and tips about the home, the area and some games to play, too. We would book again!

Over the last 3-4 years we have stayed at Ian’s at least 10 times while visiting our son at Uchicago for football games and graduations. It is a very clean and welcoming place to stay. We have enjoyed this Airbnb so much we have recommended it to underclassmen families to use and keep up our tradition. Ian has been more than accommodating for us to book and has responded very promptly when asked for favors. Overall, I would give it a 10/10!

Absolutely amazing host. The space has everything you could think of and more, and he’s incredibly responsive/available. Bed is very comfortable and the apartment is easy to find/get in and out of.

From the moment we arrived, everything about this Airbnb was spot on. The listing was 100% accurate—from the layout and amenities to the beautiful decor and serene location. What you see in the photos is exactly what you get (and maybe even better in person). What truly made our stay stand out was the host’s genuine hospitality. They were incredibly responsive, proactive with communication, and went out of their way to make us feel at home. Thoughtful touches like a personalized welcome note, and real care for our comfort and experience. The place was spotless, well-stocked, and every detail had clearly been thought through. Whether you’re here for a weekend or a longer retreat, you’ll feel cared for and completely at ease. Highly recommend to anyone looking for a reliable, welcoming, and exactly-as-promised Airbnb stay!

Spacious and clean place in the quiet, convenient and safe area! The host is very friendly and response quickly when you have any questions!

Really enjoyed the spaciousness Carmen’s place offered my brother and I. The living room was my fave with its open concept. Just be vigilant at night and you’ll be fine. Don’t hesitate to book!

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!!!

Terrific apartment, and spotlessly clean. We were only 2 people, but it had a king and a queensize bed in 2 separate bedrooms, as well as a comfortable and well dfurnished iving room. Very modern and up to date.. Kitchen was ample and well equipped and stocked with basic staples. We didn't meet our josts ut they were responsive to our messages.

I would totally stay again! Location is close to the mall and other stores. Very convenient, clean and modern style. Parking is also convenient! Will totally stay again when I visit!

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!

It was a very cozy apartment with a nice set up. Easy access to university of Chicago and the lakefront trail. We really enjoyed our stay!

My daughter and I stayed at Izakaya Studio on a recent visit to Chicago. The studio is great and Brett made it so easy to locate everything we needed to make our stay enjoyable. The next time we stay I hope to spend more time exploring the neighborhood because there were so many restaurants and shops to choose from (lots of open-air patios and decks which would be so nice during the summer season). The walk to the blue line El stop felt safe and quick. We loved the studio's layout. The kitchen and bedroom areas were separate and Brett has two big, comfy chairs for relaxing, and ample island space for eating or using as a work space. My daughter had some virtual work meetings and the Wi-Fi was reliable. The kitchen was well stocked with everything you'd need for meal prep. We ate out each day, but our delicious breakfast take-out came from a place right up the street called Yolk. I highly recommend the Izakaya Studio for a relaxing and fun visit to Chicago.

Great location and property!

Great stay at Anne’s place. She was very communicative and went out of her way to ensure we were comfortable. We would definitely recommend to anyone coming to the Chicago area!

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.

I planned a Bachelorette Party for 8 and we all enjoyed our stay! Kai and Jaiva were really nice and great with communicating. The place was nice and we’d would book again! We had a great time in CHI and recommended booking with these host.

Beautiful place to stay in Pilsen area just what we wanted! Close to downtown and amazing places to eat all around. Easy access to a lot of things to do. Beautiful place, extremely clean! We definitely enjoyed our stay at Laura’s!