Kid-friendly holiday rentals in Woodlawn, Chicago

My family of 5 including my elderly parents had a lovely stay at Rachel and David’s house for our son’s graduation from UChicago. It is in a quiet location that is very close to the university. The hosts were very friendly and flexible. The place is spacious, light and airy and extremely clean. The beds (especially the two large bedrooms upstairs) had usually comfortable beds. All in all it a 10 out of 10!

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.

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!!

This was a fantastic find! My whole party loved the place. It was clean and wonderfully located in a peaceful neighborhood close enough to transport to walk but far enough from the noise and bustle of downtown. Shawn was very responsive to any questions I had and was super kind and friendly! I absolutely would stay here again!!

It was a nice break from the hustle and bustle of the big city. A few great restaurants just a couple blocks away. And just a block away from bus stops.

Perfect location! Not far from the best things to do in the city. The neighborhood is quiet and safe. I would 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!

Carol was a wonderful host! So responsive and incredibly sweet and patient. My family and I had some last minute changes to our reservation as well as late check-out needs, and Carol generously accommodated all our needs and was very helpful throughout the stay.

Great place in a good location! Wonderful neighborhood. Was easy to find and near main road on a frontage road, but you would never know it by how quiet things are. Highly recommended.

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

Excellent communication. Easy access to the apartment. Located in a safe building and a quiet neighborhood. I would both recommend the Oaklawn Oasis and stay here again.

It was very well maintained, and the apartment felt very peaceful. The area is also very nice, everything you could need is within 10 minutes walking distance.

This was my first time booking with Airbnb and I was not disappointed. The airbnb was even bigger than what we expected based on the pictures, a lot of a space and the decor was so cool, we all loved our rooms, it felt like we were at home. The apartment smelled so cozy when we first stepped in and it had great natural lighting and amenities. The neighborhood safety was average, we never felt unsafe, and the security to get into the airbnb gave us that extra peace of mind. I will definitely be booking here again if I return to Chicago.

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.

Really enjoyed my stay, the space was clean and setup with everything a guest would need. I can tell they considered the details when setting up the space. It was also very spacious!

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!

We had a great time here. The place is really cozy and located in a nice neighborhood with plenty of stuff in walking distance. Totally worth it.

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!👍👍

Milan runs a professional Airbnb service and promptly responded to all our queries. We stayed at Apartment No. 605 which, was clean and had all the required amenities for a comfortable stay.

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.

Crazy clean, super breezy place to stay. Neighborhood is fine, but not a lot of amenities. But it was a great place for us to be.

We enjoyed staying at Kaye's place and felt right at home. It was perfect for visiting our son, who also lives in Rogers Park. We've come to love this neighborhood: It's so peaceful, and within walking distance of Lake Michigan and good places to eat. Kaye's garden apartment is on a quiet street and has a very secure entry. The photos are accurate, but if anything it is actually more spacious than it looks. Kaye is a generous host: There’s plenty bottled water, plenty of towels, comfortable bed linens. We would definitely stay here again!