Kid-friendly vacation rentals in Oak Park

Great place in a great location. Would definitely book again!

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!!

David’s place was AWESOME!! Everything was great and homie. David was awesome with responding and made sure we were good. I had two past reviews in which they could have easily sparked David to not let me book with him. But he was open minded and heard me out unlike some other host. All reviews are not honest and the details can be off by mishaps. But I appreciate his openness, niceness and overall just awesomeness. Definitely an awesome place for an affordable price. The neighborhood is nice as well and a great out door seating area in the back yard. I’ll be booking again. THANK YOU DAVID ❤️

Excellent place to stay if you want to be in a “suburban-feel” of the city: you’re in a neighborhood that is steps away from a “main street” walkable area with shops. The two parking spots are very convenient and the main floor is so thoughtfully decorated and furnished. Everything is 5 stars, just want to make a few notes: be wary of the stairs as they can be a little slippery if you don’t have any grippy socks or slippers and there is only one full bathroom so you’ll have to share this with the other guests, also there are blinds but no blackout curtains so you’ll wake up with the sun. The neighbors are very nice, but if the kids are out and about you will hear them clearly. Would 100% book again!

It’s a nice, quiet neighborhood. Definitely felt safe. The space was clean and comfortable. Perfect for a one night stay in Chicago.

Beautiful home, exactly as described and uploaded. Jaime/Erika were amazing in regards to questions, concerns and communication! Will definetly book with them again in the future!

My boyfriend and I had a fantastic weekend at Gladys’ place. She was super responsive, and check-in was easy with clear instructions. The apartment was cozy and modern, but still felt homey—like our own space for the weekend. It was clean, well-kept, and had thoughtful touches like a Brita pitcher, fresh towels, sheets, and a stocked kitchen. The layout was cute and the decor was simple but perfect—more personality than a hotel room without being cluttered. One of the highlights was the bus stop literally 10 feet from the door, which made getting into southern Chicago (via bus to the Blue Line) super convenient. We also loved walking to Dunkin’ each morning once we realized how close it was. The location felt peaceful but still had a few cute restaurants nearby. We never ran into the hosts, but it felt private even with the shared entry. This stay is in our top 5 Airbnbs—perfect for a couples getaway! Thank you, Gladys, for being such a thoughtful host!

Super cute house and would definitely stay here again, wish we could have stayed in town longer! Great location to Uber downtown for an evening.

great spot for a show at the allstate arena. safe neighborhood with a lot of good food options. easy to get into the city

This was my second time staying in Matt’s home. It is clean, comfortable, beautifully appointed and has many extras that make you feel ‘ at home’. I’ll be looking here 1st for my next trip to the Oak Park area. Thank you for another wonderful stay!

Very nice house for our family. L station really close to visit Chicago. Game room to enjoy evening with family. We have enjoyed our stay in Keith and Valerie house.

We had a great stay and would recommend this place to people looking to explore Oak Park and Chicago. We traveled with two young kids and thought it was a good place for families, although it could be tricky for little ones who are learning to walk on stairs. The kitchen is clean and nice, only downside is there aren’t many pots & pans if you’re looking for a place to cook during your stay. All in all we really enjoyed our stay!

Really enjoyed our short stay at Jennifer’s place. She has really thought of everything you might need. Great communication. Bed was extremely comfortable. Short 10 min walk to blue line that got us to downtown Chicago in 30 mins. It was lovely to meet Jennifer on our last morning. Would highly recommend

Kettil and Caroline’s place was perfect for a quick trip! We felt right at home in this vintage house. The only thing to note is that the driveway is pretty narrow and the neighbor left their car in the way not leaving us much room to go around it leaving and entering so be careful as to not scrape the rocks on the ground. The kids enjoyed the piano and tv room and we liked the eccentric artwork. Overall I would recommend this place!

The house is decorated very warmly and is fully equipped. The host also thoughtfully prepared many little snacks. The check-in process was convenient, and communication with the host went smoothly. Highly recommend staying here!

great place, highly recommended. 30 minutes into the city and a similar distance to airport. lovely apartment and great recommendations for local eats. Leah was wonderful greeting us and making suggestions. apartment had everything we needed.

When we were first looking for a place to stay, none of the available AirB&Bs looked great. A week later, we looked again, and suddenly Julia's place popped up. It was so much better looking, and with a fairer price, than any others I could find in the list. A two-bedroom that is a *real* two-bedroom, for the price that others were charging for a pull-out bed in the living room. It was just as beautiful in-person. We felt immediately at-home and comfortable. I'm someone who has insomnia, especially while traveling, but there, I had no problem sleeping somehow. Also, it truly is a short walk to the Blue Line, or even a just few steps from the 77 bus route, which goes to the Blue Line, or all the way right into downtown 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.

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.

This is a WONDERFUL one bedroom apartment that is both private and spacious! The owner/host has the space fabulously decorated with an eclectic mix of original contemporary artwork and antiques. Nothing is generic about the space and it has been outfitted for guests with loving care. The host, Kaye, clearly puts much trust in her guests with her charming decor and furnishings. The amount of space, the privacy and the home-y feel make it a place we'd love to return to.

The apartment was clean and spatious, better than in the pictures. It's located in a corner of Hyde Park, at a 15 minute walking distance from the University of Chicago. It is a very residential area, with not many shops or restaurants near by, but if you walk 15 minutes east you will find bars, grocery stores and a few restaurants. I came to do research in the library's archive so it was very convenient. I had some problems with the door code sequence, but Erika was very helpful and responsive. My only suggestion is that more detailed information about the check in is provided, because not everbody is familiarized with lockers and codes! But my general impression was very positive! I'd definitely stay there again.

We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

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!

We were only 15-20 mins away from where we wanted to be at most of the time, Kelly was incredibly patient and responsive to all our questions. The home is spacious and clean and the neighborhood is very quiet. We had an issue with not receiving the permits to park but it didn’t impact our stay at all. 100% would chose this place as our host again.