Kid-friendly holiday rentals in West Side

Had a nice time, was flexible about parking spots.

Erik was a phenomenal host, went above and beyond to ensure we had a comfortable stay at his house. His family were lovely people and helpful with any and all questions. Erik gave is good clear instructions on the best places to go to in the area, how to travel to the city and how to use all the appliances/facilities in the house. I couldn’t recommend him any more, he made our stay really more comforting and laid a great basis for our stay in Chicago. Cheers Erik!

Very friendly and accommodating hosts. Felt very welcome.

Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

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!

Samantha’s place is beautiful, well designed, modern, clean and it was very easy to find street parking near house. There are 3 bedrooms, the third bedroom is cabinet only, no bed there. But in one room there is a king bed for 3 people, and second bedroom with queen bed. Quiet area, close to the down town 12-15 min drive and the restaurant in walkable distance. The playground is 1 minute walk. Would definitely stay there again and will recommend to friends.

Musa was very friendly and helpful the entire time we stayed at his place. The house is big, neat and located in a nice and calm neighbourhood, ideal if you want to rest after a day in downtown. Good shops nearby so I recommend go for a walk around the beautiful Evanston.

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 loved our stay in the Pink House, which felt truly like a home away from home with everything we could possibly need. You can tell how thoughtful Niki and Sean are about their space and that they care about their guests having a lovely time - especially appreciated the comfy linens and snacks! Perfect location too with an easy walk to the L and plenty to discover just by wandering around the immediate neighborhood. Niki has all the recs.

I had a wonderful stay at this cozy garden apartment! The space was exactly as described—clean, comfortable, and thoughtfully set up with everything I needed. I especially appreciated how quiet and peaceful the neighborhood was, yet still close to everything. The location made it easy to get around, but it also felt like a relaxing retreat after a busy day. The setting added a nice touch of charm and tranquility. I’d definitely stay here again—highly recommended!

We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.

Very nice stay! In a great neighborhood, would stay again. Was everything me and my group needed!

We loved our stay! It was so clean and very close to public transit! We navigated the trains to and from Cicero into Chicago NP! We will definitely be back and we would definitely recommend staying at this Airbnb!!!

Just returned from a stay at one of the most thoughtfully designed Airbnbs I’ve ever experienced. Every detail—from the curated artwork and cozy textures to the seamless layout and soft lighting—was intentionally chosen to create a sense of calm and comfort. It felt like the kind of space that anticipates your needs before you even realize them. A perfect blend of aesthetic beauty and livable design. Grateful for the warmth, care, and creativity that went into making it feel like home. The hosts were truly exceptional—kind, responsive, and incredibly thoughtful. From the moment I booked, they were proactive in ensuring everything was seamless, checking in with just the right balance of presence and privacy. Every message was warm and genuine, and it was clear they cared deeply about creating a welcoming experience. Their attention to detail went beyond the space itself; it extended into how they made me feel—completely at ease, valued, and cared for.

Super clean and updated, 6 min walk from blue line subway entrance making it easy to get into the city without having to drive, and had everything we needed to for a seamless and comfortable weekend away! Highly recommend!

We really enjoyed our time here! There were plenty of parking spots around the apartment. We were able to park right in front and we greatly appreciated the instructions on how to get an overnight pass for the car. One note on this - if the website does not work, download the app and get the pass through that. There are also so many restaurants walking distance from that apartment and it’s such a cute neighborhood to explore the many Frank Lloyd Wright houses scattered around. As a Runner, I also appreciated Anne’s suggested running route to see all the notable landmarks around the neighborhood!

The location was great. About 15 min from downtown. The place was beautiful and clean. I would definitely book with Julia again.

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.

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.

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!

Affordable, quick & easy booking / check-in & check-out…it’s great spot for a quick trip to chicago for a night or two! We used the parking lot area across the alleyway, rented one of the spot hero spaces which was not the most convenient parking situation but it’s the city sooo kinda usual! The ONLY thing i wish that had been mentioned was that it was right next door to a fire dept. one pair of ear plugs were provided but just ya wish i had researched the location just a lil bit more… thanks again for welcoming us to stay :)

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!

Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai