Kid-friendly holiday rentals in Northwest Side

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!

A very nice house close to the metro and in a peaceful suburb. John and Daniel was very welcoming hosts and gave me helpful hints on places to eat in the local area.

Faith's place was great! The bed was super comfortable and her place was exceptionally clean! Quiet neighborhood. Easy access to highway, local restaurants and grocery store. The fresh eggs she gave us were a treat! She is an excellent communicator. Highly recommend staying at her place.

Glomery was a great host. Our first trip to Chicago, so we weren’t too sure about the safety of the neighborhood, but overall a very nice experience and had all the necessities. Very clean and tidy. Beds were so comfortable with fluffy pillows. Plenty of towels, coffee and extra pillows. Easy access in and easy street pick up for Ubers. We had a nice time and felt comfortable.

Joswe was so incredibly kind and accommodating! Being a solo traveler it felt like a home away from home. The space was clean and comfortable and felt very safe. Joswe even left freshly brewed hot coffee every morning along with breakfast! I couldn't recommend Joswe or his home enough! if I could give more stars, I would!

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!

We stayed one night and were very happy with the accommodations. Lisa was a helpful host and everything was very nice quality and squeaky clean. The bed was super comfortable and the shower was very nice with a big “rain” type showerhead AND a regular size detachable one. The neighborhood and yard area was calm and chickens were very cute! We had some fantastic empanadas at a nearby cafe called La Mulata - definitely recommend. There are a bunch of cool historical buildings nearby too (including the building the cafe is in). FYI since it’s a basement apartment (as advertised) there are a couple spots with slightly lower beams coming down from the ceiling). At 6’2” we were good to walk around without impediment, but I put my hand above my head at the lowest spot and the clearance was only about an inch, so if you are any taller, be careful or you may hit your head! Excellent place - thanks Lisa :)

I love everything about this home and all the e amenities, and the private rooftop was the greatest touch of the property Vince was amazing and very easy to reach in very fast responding.Thanks so much .

Dean was the best host my girlfriend and I have had! He is proactive, friendly, great with communication, and provides everything you need for a great stay. Not only this, but the place was extremely comforting and beautiful! We had an amazing stay and would love to stay here again! Not to mention this place is an amazing price for how nice the stay was! Thank you Dean! You rock😎

Very clean space in a safe neighborhood! Street parking was easy and plentiful. Easy 20 minute Uber into the city. Perfect for our overnight stop :) Would be mindful of ceiling heights when booking if over 6ft tall.

Zarko was super friendly and very descriptive in helping us find the house and where to park. He made us feel very welcome in his home!

We had a wonderful stay at Jay's place. He met us in person to check in and personally showed us through the house and made us feel so welcome. The house was very homey and had everything we needed. It's also in a great location in a very walkable neighborhood close to the Frank Lloyd Wright Studio. Oh, and morning coffee on the sun porch was delightful. Thanks for a great stay, Jay.

Margerita and Monique's place was exactly what we needed! In a calm and beautiful location, clean, beautifully furnished, private, and had the most comfortable bed! It was a short walk to the train and easy to get around! There was plenty of parking available! We will definitely reserve again when we visit Chicago in the future. Thank you both for opening your beautiful property to us!

Great place to stay Meticulously clean and well supplied Great area quiet walkable Host supplied all necessary instructions and really no need to contact her during entire stay. This was our second visit here and would not hesitate to stay again.

Exactly as described, just what I was looking for. Convenience of proximity to the Blue Line made it very easy for me to check off all the things I wanted to do during my stay. Thanks so much.

very private and fit the description exactly!

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.

My daughter and I stayed at Izakaya Studio on a recent visit to Chicago. The studio is great and Brett made it so easy to locate everything we needed to make our stay enjoyable. The next time we stay I hope to spend more time exploring the neighborhood because there were so many restaurants and shops to choose from (lots of open-air patios and decks which would be so nice during the summer season). The walk to the blue line El stop felt safe and quick. We loved the studio's layout. The kitchen and bedroom areas were separate and Brett has two big, comfy chairs for relaxing, and ample island space for eating or using as a work space. My daughter had some virtual work meetings and the Wi-Fi was reliable. The kitchen was well stocked with everything you'd need for meal prep. We ate out each day, but our delicious breakfast take-out came from a place right up the street called Yolk. I highly recommend the Izakaya Studio for a relaxing and fun visit to Chicago.

Great stay at Anne’s place. She was very communicative and went out of her way to ensure we were comfortable. We would definitely recommend to anyone coming to the Chicago area!

Great location, and easy access to all main streets. The neighborhood is quiet, and very safe. The people in the neighborhood were very welcoming. The condo was nice, very spacious and a great value for the cost.

Heather provided everything in this lovely, spacious, and comfortable place. It was deluxe, and it felt like home all at once. The driveway to park our car was so convenient! Access to Chicago's famous sights was easy, and when we returned from our adventures, there were neighborhood restaurants and venues within walking distance. We could also watch a movie on our favorite streaming services to end the evening. Whatever questions we had, Heather answered immediately and helpfully. We were grateful that we could check in early and sightsee on our first afternoon.

We enjoyed a week of comfortable stay at Matt’s place! We were a family of 5 people and had enough space for everyone! We came for my daughter’s wedding and it was great to have lots of things/amenities that helped us prepare for the wedding! Garage spot was helpful! Backyard peaceful and we spent some time relaxing on the deck! Adorable cozy duplex with everything you need for the relaxed and comfortable stay! Matt was respectful, helpful and very responsive! Area is great as well! Thank you so much!!

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!

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.