Kid-friendly holiday rentals in Wicker Park, Chicago

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!

Jane's house was the ideal accommodation for our visit to Chicago. The apartment was very well equipped. The area is very pleasant and it is also easy to get into the city or to the airport by metro and bus. Thanks again to Amy and Dean.

The Airbnb was perfect for my family and I. We have two small kids and this Airbnb was very child friendly! They had tons of kids items we were able to use which saved us packing and toting them through the airport. The hosts were super friendly, very responsive, and went out of their way to make us feel comfortable.

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!

Samantha’s home was clean, well kept, and had a lot of thoughtful touches, like snacks and drinks, that were really helpful when we were on the go. I also loved the dimming options for the lights in the rooms, and the bathroom had so much space and was so convenient even with more than one person using it. Samantha was also a great host who responded promptly to questions and concerns. My friend and I had a very peaceful stay here. The only down side to this location is that it’s a little far from the Loop and River North, but we knew that when we booked and were prepared. Would definitely stay here again!

Basement appartement but spacious, not too dark and benefit of the use of the outside garden. Kitchen has everything you need, and there is ample storage space. Shower is one of the better I encountered in the US. Came here to attend a conference and will definitely book again if the conference returns to Chicago. Reliable, friendly host, no question was ever one too many.

We really enjoyed our stay here! Perfect for two people. This place is really cute and unique. Love the decor and seeing all the cool art projects. This place was within a couple miles of all the places we wanted to see, especially Soldier Field, so a Uber/taxi ride was cheap and very convenient. Super cute neighborhood too with beautiful row houses both modern and original. It is a nice quiet neighborhood as well and we felt very safe! We would recommend the Iklektik/Blue Jay house to anyone visiting Chicago that wants a comfortable and cozy experience!

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!

Excellent place to stay!

Just wonderful. That was one of the most beautiful accommodations I've ever been to. The apartment is totally lovingly furnished. Everything was super clean and tidy. There are even toothbrushes, toothpaste and a sleeping mask, if you need them. The kitchen is also super equipped with everything you need. The short walk to the metro was also very convenient. We would definitely come back.

Such a beautiful, cozy space! Very comfortable beds, the perfect coffee setup and fast WiFi gave us the ability to work and play. Plus our host was incredibly responsive and communicative. Would definitely stay again!

Lovely home! Clean, stylish and comfortable. We appreciated the close proximity to great restaurants such as Engine Coffee and Flo. I got in touch with my Polish roots at the Polish Museum of America down the block. They have an intact exhibition from the 1939 World’s Fair Polish Pavilion. Also visited Holy Trinity Church where all the services are in Polish. If you are interested in the rich history of this neighborhood you might check these places out.

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!

great stay, super clean apartment, great communication on keith’s end would definitely stay again. thank you for accommodating me!

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!👍👍

Feven was very responsive to all our questions in real time. The place was perfect for four adults and two kids! The place was walkable to a few restaurants and coffee shops and easily drivable to other neighborhoods. We did happen to be in the neighborhood for the PR festival, which we didn’t realize. It made traffic a little tricky but otherwise we didn’t hear too much noise from the festivities. We found a nearby coffee shop and playground which we frequented daily and met lots of friendly neighbors on our walks.

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.

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!

We would love to stay here again! It's a great neighborhood, really walkable, lots of cool buildings to look at and friendly neighbors. We walked across Humboldt Park to the 606 and had a great urban hike. No problem with transportation or food delivery, but we also enjoyed walking to markets and restaurants nearby. The space was so cozy and comfortable... well equipped kitchen, great couch for watching TV and movies, comfortable bed and bathroom. We really appreciated the host's great recommendations, all of them were spot on!

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.

This apartment was a real gem. The back patio was so lovely to hang out on during the cooler evenings. I loved how accessible the building was to so much of Chicago, both via the blue line and the bus that stops right outside. Would definitely come back!