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Family-friendly holiday rentals in Cook County

Find and book unique family-friendly homes on Airbnb

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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 reviews

Restful Refuge, Hot Tub, Firepit, Dunes Nat’l Park

SebastianRating, 5 stars1 month ago
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!
Guest favourite

Home

4.85 out of 5 average rating, 311 reviews

Lux Urban 3BR/3BA Duplex + Parking!

RobertRating, 5 stars3 weeks ago
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.
Guest favourite

Loft

4.81 out of 5 average rating, 283 reviews

Artist Loft Duplex in a 1904 Former Factory

KevinRating, 5 stars6 months ago
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 reviews

Smart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities

BethanyRating, 5 stars2 months ago
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 reviews

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

ChanceRating, 5 stars1 month ago
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 🌟
Guest favourite

Apartment

4.98 out of 5 average rating, 264 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

ConorRating, 5 stars1 month ago
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 reviews

Spacious 2bdm unit 15min to Dwtn

Helena ORating, 5 stars1 month ago
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 reviews

Dunes Nat’l Park, HotTub, Sauna, Firepit, Foosball

Nehad Rating, 5 stars1 month ago
Great house with lots amenities. Hilary was very responsive and accommodating.

Family- and pet-friendly home rentals

Guest favourite

Flat

4.9 out of 5 average rating, 388 reviews

Sunny Logan Square Artists' home

BrandonRating, 5 stars1 month ago
Great apartment, very clean and well kept, we really enjoyed our stay!
Guest favourite

Flat

4.88 out of 5 average rating, 186 reviews

Chicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre

CrystelRating, 5 stars2 weeks ago
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!
Superhost

Townhouse

4.74 out of 5 average rating, 210 reviews

Insta Worthy Prime Spot *Patio *Parking *Fireplace

AmyRating, 5 stars1 month ago
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 favourite

Guest suite

4.94 out of 5 average rating, 154 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

YaniralisRating, 5 stars1 week ago
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.
Guest favourite

Flat

4.93 out of 5 average rating, 426 reviews

Andersonville Living

AmandaRating, 5 stars1 month ago
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!
Guest favourite

Townhouse

4.91 out of 5 average rating, 331 reviews

a SIMPLE place

JenniferRating, 5 stars3 days ago
Great stay! Steve was great and accommodating! Felt right at home!
Guest favourite

Flat

4.95 out of 5 average rating, 501 reviews

2nd floor of 1908 brick two-flat in Logan Square

TimothyRating, 5 stars3 days ago
Great apartment. Very clean and close proximity to transit, groceries, restaurants, etc. Would definitely stay here again.
Guest favourite

Flat

4.94 out of 5 average rating, 168 reviews

Aunt Linda's Apartment with a View in Palos

LizRating, 5 stars4 weeks ago
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 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

ParitoshRating, 5 stars1 month ago
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 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

JasonRating, 5 stars3 weeks ago
Great location great host will stay here again.
Superhost

Flat

4.75 out of 5 average rating, 52 reviews

The Professional's Playground

Jura Rating, 5 stars1 month ago
Very nice place, location, wellness center beautiful, highly recommend this place to everyone !!

Guest suite

4.67 out of 5 average rating, 42 reviews

Music Hot Spot’s Main Level

MichaelRating, 5 stars4 months ago
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 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

EmmanuelRating, 5 stars3 weeks ago
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!

Destinations to explore