Family-friendly holiday rentals in Andersonville, Chicago

Christine’s place was the perfect get-away for a family vacation close to home. The lake was beautiful and the place was spotless and inviting. It felt like you walked in to your own home. It’s close to places to eat and there is even a community space just a few houses down that is lively if the weather is nice. I’m hoping to come back again!

This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.

This is our fourth time staying at this home and we love it. There is a Korean supermarket (huge) a five minute walk away from the home. There are three bedrooms and three full bathrooms which makes it easy and private for everyone. Kitchen has a lot of additional things you do not see in other homes. We love staying here.

Every year we visit Cypress there are more improves and amenities. Always a great stay and so much to do. Amanda and her team run this place like a well oiled machine. We visit once in the winter and once or twice in the summer. A favorite for sure.

Amanda is the best host I’ve ever had, she is so friendly and responsive. Her kitchen was fully equipped, she gave us the option of having firewood delivered, the place is absolutely beautiful, you walk down some stairs to get to the beach. A group of 8 moms went there for a weekend getaway and it was exactly what we needed. Thank you!

This place was extremely great! It was close to downtown and lots of restaurants and food near by the bnb! Only thing I’ll say is the shower head is kind of flimsy but besides that everything is nice clean and the rooms are huge! Very peaceful and quiet over there!

Great escape from hustle bustle. Hot tub was a great addition to our visit. Would recommend for small groups.

We absolutely loved our stay at Amanda's place. We wanted a quiet weekend out of the city and this place blew our expectations out of the water. I wish we could have stayed longer. The apartment itself and the resort overall just felt so homey and everyone we ran into were so kind. This is definitely somewhere we will have to start visiting once a year.

Heather was super helpful and gave great suggestions on things to do. Perfect location less than 2 miles from Wrigley Field and about 3-4 miles north of the city. Extremely walkable with local bars, restaurants, and cafes. Lincoln Park is right next door. Uber is easy and cheap. Street parking is free at this location if you can find it. We parked outside one day when a spot opened up, otherwise we parked about a block away, again super walkable! Thanks Heather for a great stay!

Highly recommend booking here! Both hosts were very responsive and the space itself is beautiful. No problems whatsoever and would stay again in a heartbeat.

Ms. Jamie was a great host who took us in and kicked out the Red carpet for us. My wife and I celebrated 8 years of marriage and Ms. Jamie was very welcoming and everything was in ars reach she has a great location and all the information you need for the area. This was our 1st air bnb stay and we loved it

This home in Chicago was exactly as advertised. Perfect for a girl's weekend in Chicago. Plenty of space for sleeping, large bathrooms with plenty of mirrors to get ready. The house was well stocked with everything we needed for a perfect weekend. The location was great too. was able to walk to bars and restaurants or take short Uber anywhere we needed to go. Having off street parking made it even better for out of towners who drove to the destination. I would definitely book again when traveling with a large group.

We had a great stay! Quiet street, very easy check in and out, clean, and lots of space. Great for a family or small group of friends.

I stayed for about a week at Paul and Sarah's home and it was very pleasant. They provided very detailed instructions for check-in and I had no problems navigating to the building. The apartment itself is cozy and gets plenty of light in the daytime, though the floorboards were a bit creaky so I recommend treading lightly if you're someone with heavy footsteps. The TV also doesn't come with a streaming device so if you plan on watching Netflix/etc. be sure to bring your own device or an HDMI cable that can mirror a laptop. There was also an induction plate provided for light cooking which was helpful on the days I didn't want to do takeout. Overall this was a great home base for exploring Logan Square with very easy access to other neighborhoods/downtown via the Blue line and bus.

This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.

This place was exactly what we were expecting. First and foremost, it was clean and homey. The parking space was the cherry on top and made coming and going super convenient. Afsha was a great host and did a fantastic job of communicating with us. We would absolutely recommend.

Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

I had an amazing stay at this place. Felt like home.The space was clean, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable visit. The host was incredibly welcoming and responsive, making sure every detail was perfect. The location was ideal, close to local attractions yet peaceful and quiet. It truly felt like a home away from home, and I can’t wait to book again for my next trip. Highly recommended!

Great location great host will stay here again.

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.

Stephen was a welcoming host and the cabin was exactly as described. The location is secluded and quiet, but you’re also close to groceries, restaurants and fun antique stores. Kitchen is well stocked for cooking meals, and the fireplace is cozy and perfect for relaxing. Even with snow on the ground we enjoyed strolling around the property down to the lake. A wonderful stay, we’d love to visit again.

Loved everything about this place! The views were great! Close to so many restaurants, bars, museums, the bean and so much more. would definitly book this again. Thank you for sharing your place with our family!