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Family-friendly vacation rentals in Near North Side, Chicago

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Near North Side, Chicago family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite

Home in West Town

4.85 out of 5 average rating, 311 reviews

Lux Urban 3BR/3BA Duplex + Parking!

RobertRating, 5 stars2 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 favorite

Loft in West Town

4.81 out of 5 average rating, 283 reviews

Artist Loft Duplex in a 1904 Former Factory

KevinRating, 5 stars5 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.
Superhost

Apartment in The Loop

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 favorite

Apartment in Near South Side

5 out of 5 average rating, 27 reviews

Lux Loop Retreat: Amazing Views, Free Parking

GeorgeRating, 5 stars2 weeks ago
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.
Guest favorite

Condo in Logan Square

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!

Apartment in Bronzeville

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!
Guest favorite

Apartment in Near South Side

4.87 out of 5 average rating, 197 reviews

Skyline Serenity: Sauna, Hot Tub, Peloton, Views

SoutaRating, 5 stars2 months ago
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

Guest favorite

Apartment in Logan Square

4.9 out of 5 average rating, 388 reviews

Sunny Logan Square Artists' home

BrandonRating, 5 stars4 weeks ago
Great apartment, very clean and well kept, we really enjoyed our stay!
Guest favorite

Apartment in Lincoln Park

4.88 out of 5 average rating, 184 reviews

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

KatherineRating, 5 stars3 weeks ago
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 favorite

Guest suite in Portage Park

4.95 out of 5 average rating, 152 reviews

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

YaniralisRating, 5 stars2 days 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 favorite

Townhouse in Old Town

4.85 out of 5 average rating, 164 reviews

Downtown Elegance ✨ Private Yard Parking

JoanRating, 5 stars1 month ago
Great place! Plenty of beds and bathrooms! The garage was a little tight but street parking was easy. Thanks for everything!
Guest favorite

Apartment in Andersonville

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 favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 329 reviews

a SIMPLE place

AngelRating, 5 stars2 weeks ago
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.
Guest favorite

Apartment in Logan Square

4.95 out of 5 average rating, 499 reviews

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

TimothyRating, 5 stars5 days ago
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.
Guest favorite

Apartment in Irving Park

4.94 out of 5 average rating, 217 reviews

Stylish Chicago Apartment near Public Transit

KateRating, 5 stars1 month ago
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

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

Destinations to explore