Family-friendly vacation rentals in South Side

We had a wonderful stay at this apartment! The location was perfect—convenient and close to everything we needed. The apartment itself was comfortable, clean, and well-equipped. Our host was incredibly attentive and made sure we had everything we needed for a smooth stay. Highly recommend this place!

Very beautiful home that’s a short walk from pretty much everything I’m Chicago! Would 100% recommend staying here especially because it’s right by the blue line. Hans is very responsive and helpful i really appreciated having him as my host. I hope to stay here again one day.

Aaron was very friendly, communicative, and helpful. We loved the space - very cool decor and vibe, big rooms, and very close to the train.

This was an excellent place to stay for a work trip. Close to the office and plenty to do around it. Check in was easy and the room was clean and comfortable!

John’s place was incredible! We were a large group and it had plenty of sleeping arrangements for everyone in our party. Central area is HUGE and it has everything you could need and more. Check in and communication was prompt. Would definitely recommend for anyone hoping to host a large group or family get together x

A very comfortable rental. Clearly well maintained,spotless, and every amenity necessary to make renters feel at home. Spacious layout. The linens were all of nice quality. The shower/tub was stellar. Highly recommend this rental. With family in the area we have stayed at 7 rentals in the Logan Square area. Top marks to this one!!!

Everything was great. We did not have temp controls..one bedroom was really warm and the other very cool. Other than that no issues.

The apartment felt roomy and comfortable. Interior was nicely decorated (came away with a few ideas!!). Location is as other reviews. A bit of walking if you like but buses are very close to get you to Blue Line stations. Plenty of shops and food options close by. Aleks and Kyle were as you would want hosts to be, present but not overbearing. Point of note, stairs up to front door are quite steep and might be troublesome for some if carrying large, heavy suitcases. Overall, would thoroughly recommend a stay here.

The location was great for us and it met our expectations. Very walkable, close to a coffee shop we liked, small restaurants, public transportation, park and DePaul University. It also felt safe in the evening. Heather communicated well and very fast. The coffee it the Kitchen hit the spot first thing in the morning before venturing out. We liked the "old building feeling" which was part of the charm. Would stay there again. Thank you!

Jamie was an amazing host and the stay far exceeded expectations! From the detailed information about the city to the decor in the apartment, it was a stay to remember! Jamie was warm and accommodating as was the neighborhood and apartment! I hope to make this a yearly trip and stay here, with Jamie as my host I would always have a great time!

Our stay was great! Alexandra was incredibly responsive for any question that came up and even provided us tons of recommendations for restaurants and things to do in the area. The place was very clean and accommodated our family comfortably. Highly recommend this stay!

We had a wonderful stay at Joseph’s place in Andersonville. The beds were very comfortable, the apartment is located on a quiet street yet very near restaurants and stores. The communication with the hosts was very easy. Our family thoroughly enjoyed our stay at Joseph’s.

Steve’s Airbnb was just what we needed when visiting Chicagoland for a long weekend. The place is dog and kid friendly, fully equipped with a high chair and pack n play for our baby. We would happily stay again when we’re in the area.

we had a great time and the hosts were very kind and helpful. thank you.

Great communication, exactly as pictured, and everything my family needed for the trip!

Lovely views of the train, statues, and skylines. Fresh and clean space. Shower was warm and refreshing. Host was extremely responsive and helpful. Easy check out and lovely doorman to support the process. Would stay again!

Perfect location for a visit to Chicago. You can walk to everything…Magnificent Mile, Millennium Park, the river, amazing restaurants, etc. Also, the apartment is wonderful with excellent hosts. Highly recommend!

The shower was spacious and the towels were incredibly soft. I found the mattress and sheets were very comfortable and clean. The pool looked well kept, even though I did not use it, and the yard/gardens are beautiful. It is close to the Sox's park, whatever they call it now. Also the amenities are outstanding, especially for the price. I could have easily paid twice as much to stay at a hotel. I would highly recommend patronizing this property to anybody.

Rose is a totally lovely and nice landlady. Very helpful. I felt super comfortable and taken care of during my stay with her and her family.

Great stay. Great location. Timely communication 5 stars!