Kid-friendly vacation rentals in Woodlawn, Chicago

We had a great stay. The house was perfect for our group - 4 adults and 1 baby. Very clean, with great facilities. The wireless chargers were so helpful as we were international visitors. Also, the provision of tooth brushes, mouthwash and razors in the bathroom was a great bonus. Plenty of towels, comfortable beds and lovely location near the Prairie path made it a wonderful stay.

Thank you for being a great attentive host. We look forward to our next stay here!

This house was just as described on the website. It was in a great location. The house is beautiful and clean. Walking distance to Wrigley, many restaurants and also the train. We really enjoyed our stay.

We came for The Weeknd concert in the city, so we got ready there, then spent the night and morning in the house. It was a beautiful house and felt super peaceful and safe! The beds were insanely comfy and we all slept so well! So much space! Everything was just so homey and comfortable.

We had a great stay at Kathleen’s. My son especially enjoyed the air hockey table! The house worked great for the four of us. Kathleen was very responsive with restaurant suggestions and even dropped by some batteries when the remote died.

The 7 of us had a comfortable stay at Kenya’s place. It was extremely close to the venue we were attending that weekend so it made our drives back and forth fairly convenient. It was nice to have at least two full bathrooms and multiple rooms to congregate and spend time in. She very kindly allowed us to extend our check out time ahead of time as well since our event didn’t end till the middle of the day.

Well, I must say we had a great time at this Airbnb. The place was exactly how it was described. Very clean very cozy. Jacob responded in minutes and was very nice. I would definitely recommend staying here.

The house was very spacious and young children friendly. There is even had a cabnet full of books for my kids! My kids loved the play structure and we were able have a camp fire.

Visited Chicago with family from LA and decided to stay in this beautiful home. We loved the spaces throughout the home especially the master bedroom’s bathroom. It was quite cold and windy when we were there and the heated flooring and hot tub in the bathroom really warmed us up. The neighborhood has great restaurants nearby that we visited and it was very peaceful. Nicole and Matt provided parking stickers and it was really convenience for us. We had a great time!

Marla and James were great— very friendly, gave simple instructions on how to get in, check out, etc. Well stocked kitchen (great for us, staying more than a few days— it was nice to not need to rely on takeout 100% of the time). Beds were super comfy and rooms had plenty of storage space. Wish there was a bit of a different couch but the futon was still great for the time we spent at “home” in the living area. Lots of different books on the shelf to get into. Neighborhood is very cute and safe— we walked, used the bus and the train pretty exclusively at all times of day, despite bringing a car. 15min walk off the brown line, and other bus stops around 10min walk as well. Recommend this spot for any small group of friends or family traveling and wanting to see the city.

Staying at Jenny's place was fantastic! She was always responsive and helpful. The apartment itself was cozy and pretty quiet, especially for a Chicago unit. I hope to stay there again in the future!

Jessica’s place was perfect for a weekend trip to Chicago with family. She was a very responsive and helpful host. We loved how walkable the location was - it was so easy to grab a coffee or bite and check out the farmer’s market and zoo. We highly recommend her space!

James was great and so was the airbnb, think very highly of him and his air bnb.

It was a good stay when I needed extra space for visiting family in the city.

The living room was very comfortable and provided a great space for all our group to hangout after a wedding. The extra bedding and coffee was a nice plus!

Great location! The place was very easy to find and within walking distance some really good restaurants. Loved our stay!

There’s nothing but good words for our stay at Zirrell’s place. She was very responsive. It is accessible, easy to figure the check-in instructions, very cozy & clean. We felt comfortable almost like home . If visiting Chicago with company I would recommend Zirrell’s place

I stayed at John’s Airbnb during my trip to Chicago, and I honestly couldn’t have asked for a better spot—especially being right in the heart of Chinatown. The place was spotless, super cozy, and had everything I needed for a comfortable stay. You can tell John takes pride in keeping it clean and well-stocked, which I really appreciated. What made it even better was the location. Chinatown in Chicago is such a vibe—full of culture, energy, and some of the best (and most affordable) eats in the city. If you’re a foodie like me, you’ll love exploring all the spots nearby. One place I highly recommend is Hing Kee. Their hand-pulled noodles and dumplings are on point—fresh, flavorful, and easy on the wallet. If you’re looking for a clean, convenient, and authentic Chicago experience, especially in Chinatown, John’s place is the move. I’d definitely stay here again.

Loved this condo. We had 7 adults staying and felt comfortable. Having a dedicated parking space was super helpful and on street parking was easy. Please note this is a 3rd floor walk up so if stairs are a problem you need to consider if this works for you. Easy access to Midway airport and Chinatown were also great features.

Josh was an excellent host! Provided great instructions for entry, exit, parking, and even some details related to working different things in the home. Beautiful location for Wrigley & restaurants. Also an easy walk to a grocery store.

Great responsive host. The place was clean and check in was easy. They were very responsive and accommodating. The location was excellent and easy to navigate with plenty to do within walking distance.

Annie was very proactive in communication. the location was quite incredible, parking is difficult at times, but the rooms and comfort were exceptional.

Daniel was a perfect host. I needed to change dates and he was very responsive. The space was perfect for our family of 3 adults and 2 children. We found a great Breakfast restaurant within walking distance.

We loved the comfortable condo with lots of light. It was an excellent location for getting anywhere. We took the Halsted as well as Clark St buses and the red line at Fullerton. It was very relaxing to have breakfast in a beautiful space before heading out for the day.