
Kid-friendly vacation rentals in West Side
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in West Side
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for West Side kid-friendly rentals
Kid-friendly house rentals

Spacious & serene in hip spot. Sleeps 4.
Abby is a wonderful host! She is very respectful and is there if you ever need anything! The place was nice and clean. I would not hesitate to return again.

Single bed room with Asian decor in family home
John’s place is a great place to stay if you are visiting Chicago! It’s clean, in a nice neighborhood, and close to downtown Chicago. John and his family are very welcoming and friendly! I would recommend their place in a heartbeat!

Safe & Clean King size Bed Next to Ohare/Rosemont
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!

Retro Modern Bungalow | fire pit • free parking
We had a great stay at this place. The location is very nice. Get to be outside of downtown still while close enough to visit whenever you’d like. The retro vibes of the home itself is very cozy and unique. Will definitely book again if we ever come back.

Antique Filled Home
Beautiful and serene neighborhood, mesmerizing antique decor and genuine friendliness from Tom and Grace. Would love to return to relax in the beautiful backyard garden and read on the front porch. We felt welcomed and at home.

Private Bed and Bathroom in a Great Location
It couldn't be better. No, it is not a luxury accommodation. It is the classic Airbnb, namely a room in a privately used apartment. Diana lives and works there alone. She rents out a room with an opposite bathroom, which is only used by guests, mainly out of interest in foreign cultures. The accommodation is located in the Ukraine quarter, which is very quiet and about 30 minutes outside the downtown. In the morning, Diana surprised us with a prepared coffee machine (just turn it on), a few cookies and a lovingly prepared fruit plate. Bus no. 66 takes you quickly to the city center. We enjoyed the time in Chicago very much. We received a lot of information from Diana, but also had very personal conversations. If we come back to Chicago, we'll check in with Diana! Thank you for the authentic and so lovely stay!!!

Skyline Room, near Medical Ctr, Upstairs
Enjoyed my stay, very clean and comfortable. Very convenient and close to airport, train station, bus stop, etc. The host is amazing and responsive to guest’s needs.

Clean, Cozy 1st Floor Flat, Kitchen, Parking
Great location. Due to a family emergency, I didn’t get to fully rest and sleep in as originally planned but the time that I was there, it was peaceful. No one bothered me. I didn’t realize that checkout was at 10 and not 11. The host was nice enough to extend for the 1 hour. Very helpful, responsive, friendly. I wish it was available to extend for a few more days.
Kid-friendly apartment rentals

City-Accessible Basement Retreat
I absolutely loved my stay it was very peaceful and clean I felt right at home!

Cute, Clean, Cozy Apartment in Pilsen
This space was perfect for my weekend getaway! Checking in was super easy, and once inside I felt at home! If you’re tall like me you might have to crouch down a little bit in some parts of the apartment but other than that, I was super comfortable. I loved how cozy this space was, everything was also super clean! This BNB is about 7/8 minutes away from one of the buses that takes you into the city, which was super convenient! I stayed out late twice while staying here, and I will say the streets are a little dark, so I recommend walking in groups / walking back quickly (LOL). My friends also really liked the space! Overall a really great experience, thank you so much Leigh-Anne!!!

Decompress on a Sophisticated Chaise at a Glamorous Hideaway
Simidas very sweet and hospitable. I didn’t need anything but felt cared for. Place is nicer than I thought usually you expect it to be smaller but was very spacious. Great area Felt safe Would come again.

Spectacular Pilsen Studio for 2!
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!

2 bedroom apartment near train line and bus lines!
I stayed here for about a week and I gotta say I had an amazing time here in Chicago. I would rent this place again for sure. I loved the layout of the home and it was very clean when I arrived. Looks exactly like the pictures provided and the hosts were very attentive and responded fairly quickly. Also loved the neighborhood, there were many places to go eat at and shop walking distance and it was quiet and peaceful and night. Would definitely recommend this place to stay at.

Rockin' 2Bed steps to shops/food/train
Listing as described. Very good bedding. The bathroom was compliant, just the bathtub might need a little refreshment but it was fine. The other comments said that the neighbor upstairs was a little noisy, indeed we heard him but it was reasonable. The accommodation is a 10-minute walk from the metro. From the metro, it takes 40-45 minutes to reach the hyper center of Chicago.

Chicago Airbnb Newly Remodeled 2-Unit Apartment!
Brittney's place was easy to get to from the Blue Line train. The place was clean and comfortable. Brittney was very responsive to our questions and checked in with us to assure all was well.

Cozy Vintage Chicago-Style, 1 bed with Cable
Great apartment, great location. Stayed close to family but really enjoyed the Arts District neighborhood while we were here.
Kid-friendly condo rentals

Lovely top floor 2BR/2BA, steps from everything!
The location was great. About 15 min from downtown. The place was beautiful and clean. I would definitely book with Julia again.

Modern Izakaya Studio in Wicker Park
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.

Your perfect place looks like?
In town for work and this was perfect place to stay for team. Easy walk to the shops and restaurants in Fulton Market while still providing a peacefully quiet setting. Bright, open and clean apartment with 3 large bedrooms. Nice kitchen for all meal-preparing needs If you don’t want to cook, no problem. Some of Chicago’s best restaurants are just a short walk or quick uber ride.

Newly updated 1BD/1B in Old Irving 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.

3D Tour! Designer Condo near Logan Square
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!

Modern Chicago Movie Themed Apt
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!

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen
Beautiful place to stay in Pilsen area just what we wanted! Close to downtown and amazing places to eat all around. Easy access to a lot of things to do. Beautiful place, extremely clean! We definitely enjoyed our stay at Laura’s!

Cabin 302 at 747 Lofts
Great place to stay during our trip, looks exactly like the photos and felt very central to all the places we wanted to go. Train entrance was very close and several establishments within walking distance. Host was extremely helpful and proactive with check in assistance and responded quickly.
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- North Side Vacation rentals
- South Bend Vacation rentals
- South Haven Vacation rentals
- South Side Vacation rentals
- Saugatuck Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Rentals with a balcony West Side
- Private suite rentals West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Rentals with lake access West Side
- Rentals with a hot tub West Side
- Townhouse rentals West Side
- Apartment rentals West Side
- Rentals with a fire pit West Side
- Fitness-friendly rentals West Side
- Loft rentals West Side
- Rentals with a patio West Side
- House rentals West Side
- Waterfront rentals West Side
- Rentals with an accessible height bed West Side
- Rentals with pools West Side
- Rentals with a washer and dryer West Side
- Rentals with outdoor seating West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Guesthouse rentals West Side
- Rentals with a fireplace West Side
- Condo rentals West Side
- Rentals with breakfast West Side
- Hotel rentals West Side
- Rentals with a home theater West Side
- Rentals with beach access West Side
- Kid-friendly rentals Chicago
- Kid-friendly rentals Cook County
- Kid-friendly rentals Illinois
- Kid-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
- Things to do West Side
- Food and drink West Side
- Things to do Chicago
- Art and culture Chicago
- Sightseeing Chicago
- Food and drink Chicago
- Tours Chicago
- Things to do Cook County
- Tours Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Things to do Illinois
- Tours Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Food and drink Illinois
- Things to do United States
- Sightseeing United States
- Tours United States
- Food and drink United States
- Entertainment United States
- Wellness United States
- Art and culture United States
- Nature and outdoors United States
- Sports activities United States