Kid-friendly holiday rentals in Wicker Park, Chicago

We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!

This was an ideal place for our visit—we could walk about 15 minutes to Wicker Park or just 5 or 10 minutes to the Blue Line. Beautiful, large unit. Great space, and well stocked with extras.

Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Had a great five night stay, still only scratched the surface on what this fun neighborhood has to offer. Cute little house, squeaky clean and well organized and quiet even though close to anything you would want (including blue line). Host team super responsive, would 100% stay again!

We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

Was a very nice and relaxing place to stay after spending time in the city! Really close to multiple bus stops which made the public transport really easy to access. The inside was very clean and nice, the bed is extremely comfortable! Would stay again!

Lovely place! Nathaniel was very responsive and accommodating to us while in Chicago! Made everything easy and created a homey space for us to enjoy. Would definitely stay again.

This was our second time staying here, and everything was as comfortable as the first time. We highly recommend this place.

What a delightful place this was to stay at! Loved the wood floors and comfy bed. Peaceful and safe area for a solo business traveler. Plenty of parking in front. Deck was adorable with the flowers. Had a full kitchenette stocked with tea and coffee. Mindy was so responsive and kind!! One of the best places I’ve stayed at!!

Emily’s place is peaceful and homey, yet right in the heart of a vibrant neighborhood. Wicker Park was a nice walk from her home as well. TONS of restaurants and shopping literally a couple of blocks from her house. The train stop is a 5 minute walk away and downtown is less than a 15 minute uber ride. Emily is a very considerate and communicative host and I would stay here again. Thank you for sharing your home with me!

Christina was the best! Love her space - so beautiful and thoughtful with the amenities. The location is also very central to many things in the city. Highly recommend!

Hena was super attentive and reached out to check in a few times during our trip. The apartment was clean and comfortable and a great place from which to explore Pilsen or hop on bikes and head up into the busier parts of the city. Thanks for a great trip!

One of our favorite Airbnbs in Chicago, it has a great central location and great street parking (with a permit). It's cute. clean, and quiet. I highly recommend!

Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.

This place is as described. Very clean. The sofa was very comfortable. Nice little local bar at the end of the block. Very cute neighborhood. Only con, is if you are a light sleeper the ceiling fan in the bedroom is a bit noisy. It didn't bother me while sleeping but it's noticeable when awake.

This was a wonderful place to stay! Great neighborhood and so close to the train station easy to jump on and get to the heart of downtown! Love the place and was perfect for what 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.

Our stay was fantastic. We have three children and everyone was comfortable. The location was perfect, the hosts were clear communicators and quick to respond. We would stay here again in a heartbeat.

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.

This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

I had an amazing stay! Place was very accurate to the post on Airbnb and the host was very polite with clear instructions, and check in! Thank you for providing such an amazing Chicago experience for me and my husband!

We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.

We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!

Great stay at Kathleen's! We already knew we loved the area having lived a few blocks away for many years so we felt right at home. Perfect for guests with an infant or toddler - nice high chair and pack-n-play, our little one slept and ate well all week.