
Family-friendly holiday rentals in Cook County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Cook County
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Cook County family-friendly rentals
Family-friendly home rentals with a hot tub

Home
4.58 out of 5 average rating, 66 reviewsRestful Refuge, Hot Tub, Firepit, Dunes Nat’l Park
It was a great stay, myself and the other guests had a great time staying here. Other than a few of the beds being stiff, the rest of the amenities were great, everything worked as expected. Also a great view of the lake from the balcony!

Home
4.85 out of 5 average rating, 311 reviewsLux Urban 3BR/3BA Duplex + Parking!
This is our fourth time staying at this home and we love it. There is a Korean supermarket (huge) a five minute walk away from the home. There are three bedrooms and three full bathrooms which makes it easy and private for everyone. Kitchen has a lot of additional things you do not see in other homes. We love staying here.

Loft
4.81 out of 5 average rating, 283 reviewsArtist Loft Duplex in a 1904 Former Factory
Aaron was very friendly, communicative, and helpful. We loved the space - very cool decor and vibe, big rooms, and very close to the train.

Home
4.55 out of 5 average rating, 130 reviewsSmart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities
This was such a beautiful spot right by the beach! The house was so nice, we didn’t want to leave. Hilary was also super responsive and helpful.

Home
4.53 out of 5 average rating, 158 reviewsSecluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
This was a very private, gated home with a beautiful interior and exterior. We loved the hottub and the fact that we were able to bring our fur baby!! Would highly recommend for anybody looking to travel to Chicago on the south shore train line! 5 stars 🌟

Apartment
4.98 out of 5 average rating, 264 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
We had an awesome and memorable experience for our christmas vacation in Chicago. Bryan was very responsive to any of our questions and was an overall great host with an awesome, super comfy place. During our stay we even had a minor appliance issue and Bryan replaced the whole thing and got it working again within the hour on a Sunday! If you stay here you definitely won't regret it!

Flat
4.45 out of 5 average rating, 20 reviewsSpacious 2bdm unit 15min to Dwtn
This place was extremely great! It was close to downtown and lots of restaurants and food near by the bnb! Only thing I’ll say is the shower head is kind of flimsy but besides that everything is nice clean and the rooms are huge! Very peaceful and quiet over there!

Home
4.67 out of 5 average rating, 93 reviewsDunes Nat’l Park, HotTub, Sauna, Firepit, Foosball
Great house with lots amenities. Hilary was very responsive and accommodating.
Family- and pet-friendly home rentals

Flat
4.9 out of 5 average rating, 388 reviewsSunny Logan Square Artists' home
Great apartment, very clean and well kept, we really enjoyed our stay!

Flat
4.88 out of 5 average rating, 186 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Great location with so many restaurants within walking distance. Easy to get anywhere. Looking forward to returning in warmer weather and enjoying some walks through Lincoln Park!

Townhouse
4.74 out of 5 average rating, 210 reviewsInsta Worthy Prime Spot *Patio *Parking *Fireplace
We had a wonderful stay with our family. The location was better than expected. Close to so many things & very walkable. Alexandria was really helpful & kept in constant contact with us. We had a wonderful stay!

Guest suite
4.94 out of 5 average rating, 154 reviewsCozy Home Living, Dogs, Kids, Free Parking, 420 OK
I definitely highly recommend staying at this location. I’ve had an amazing stay. I’m also pleased that this location allows pets so I was very happy to bring my doggo. Jamie is an amazing host. If you are a first timer in chicago, She will have you prepared to explore the windy city.

Flat
4.93 out of 5 average rating, 426 reviewsAndersonville Living
Place felt bigger than the pictures and was perfect for myself and pup plus Parents & Aunt who were visiting for Christmas. Great location to the wonderful restaurants of Andersonville and kitchen was great for when we wanted to cook. Would definitely stay again!

Townhouse
4.91 out of 5 average rating, 331 reviewsa SIMPLE place
Great stay! Steve was great and accommodating! Felt right at home!

Flat
4.95 out of 5 average rating, 501 reviews2nd floor of 1908 brick two-flat in Logan Square
Great apartment. Very clean and close proximity to transit, groceries, restaurants, etc. Would definitely stay here again.

Flat
4.94 out of 5 average rating, 168 reviewsAunt Linda's Apartment with a View in Palos
Linda's place was very comfortable, tastefully decorated, light and bright. The home had everything we needed for a week stay. It was bigger than I expected and a good place to relax, with some noises from other units, but overall it was quiet. It was close to everything and in a good area. Linda was very pleasant and attentive to our needs. We would definitely stay here on another occasion.
Family-friendly home rentals with a pool

Flat
4.64 out of 5 average rating, 59 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
I had an amazing stay at this place. Felt like home.The space was clean, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable visit. The host was incredibly welcoming and responsive, making sure every detail was perfect. The location was ideal, close to local attractions yet peaceful and quiet. It truly felt like a home away from home, and I can’t wait to book again for my next trip. Highly recommended!

Flat
4.76 out of 5 average rating, 211 reviewsStylish Corner 2 Bedroom in the Heart of Chicago |
Great location great host will stay here again.

Flat
4.75 out of 5 average rating, 52 reviewsThe Professional's Playground
Very nice place, location, wellness center beautiful, highly recommend this place to everyone !!

Guest suite
4.67 out of 5 average rating, 42 reviewsMusic Hot Spot’s Main Level
Rose is a totally lovely and nice landlady. Very helpful. I felt super comfortable and taken care of during my stay with her and her family.

Flat
4.77 out of 5 average rating, 232 reviewsLuxury Corner 2 Bedroom in the Loop | Roof Deck
Loved everything about this place! The views were great! Close to so many restaurants, bars, museums, the bean and so much more. would definitly book this again. Thank you for sharing your place with our family!
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