
Family-friendly vacation rentals in Near North Side, Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Near North Side, Chicago
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Near North Side, Chicago family-friendly rentals
Family-friendly home rentals with a hot tub

Home in West Town
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 in West Town
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.

Apartment in The Loop
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 !!

Apartment in Near South Side
5 out of 5 average rating, 27 reviewsLux Loop Retreat: Amazing Views, Free Parking
This place is just as amazing as Amanda me being a Busniess owner i would have to say how she treats her air bnb as a business is top tier level and experience she had every amenity you can think of and was well stocked down to the tee i could say this was the best Airbnb I’ve ever stayed in along with Amanda being the best host I’ve ever encountered views were amazing also along with her decor as i am a contractor i pay attention to a lot of detail in a home and man was she on it very motivational words and her frame pictures lets me know how dedicated she was to her Busniess and craft will definitely stay her again when i visit.

Condo in Logan Square
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!

Apartment in Bronzeville
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!

Apartment in Near South Side
4.87 out of 5 average rating, 197 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Plus: - Amazing view of the Chicago skyline - The place has literally anything you would need and more - TV in every room including the bathroom. Amazing - Everything was labeled making things easier Negative: - The beds were a little stiff in my opinion - Some of the ceiling fans didn't work - The neighborhood was a little sketchy at night. nothing the owner can do just a fact.
Family- and pet-friendly home rentals

Apartment in Logan Square
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!

Apartment in Lincoln Park
4.88 out of 5 average rating, 184 reviewsChicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre
Great visit to Chicago! We loved Heather’s place and found it to be very quiet but close to things. The beds are comfy and the apartment was very clean. Heather was very clear and communicated proactively which was really nice.

Guest suite in Portage Park
4.95 out of 5 average rating, 152 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.

Townhouse in Old Town
4.85 out of 5 average rating, 164 reviewsDowntown Elegance ✨ Private Yard Parking
Great place! Plenty of beds and bathrooms! The garage was a little tight but street parking was easy. Thanks for everything!

Apartment in Andersonville
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 in Hoffman Estates
4.91 out of 5 average rating, 329 reviewsa SIMPLE place
What a perfect place to spend the weekend with my mom and daughter. Steve was very friendly and responsive. The house is very nice and clean. It was a perfect fit for us.

Apartment in Logan Square
4.95 out of 5 average rating, 499 reviews2nd floor of 1908 brick two-flat in Logan Square
A fantastic place to stay when visiting Chicago. Close to a great co-op, restaurants, record stores, thrift stores, public transportation. The apartment was clean and spacious, communication was easy and thorough. Would love to stay here again the next time we visit.

Apartment in Irving Park
4.94 out of 5 average rating, 217 reviewsStylish Chicago Apartment near Public Transit
One of the cleanest places I’ve stayed and a good home base for our trip. Loved having a parking spot.
Family-friendly home rentals with a pool

Apartment in The Loop
4.64 out of 5 average rating, 58 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!

Apartment in The Loop
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.

Guest suite in Berwyn
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.

Apartment in The Loop
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!
Quick stats about vacation rentals that are family-friendly in Near North Side, Chicago
Total rentals
550 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
23K reviews
Pet-friendly rentals
270 properties allow pets
Rentals with a pool
210 properties have a pool
Rentals with dedicated workspaces
410 properties have a dedicated workspace
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