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Family-friendly vacation rentals in Woodridge

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Popular amenities for Woodridge family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite

Apartment in The Loop

4.97 out of 5 average rating, 29 reviews

The Playwright's Palace

CarlosRating, 5 stars2 months ago
We had a wonderful stay at this apartment! The location was perfect—convenient and close to everything we needed. The apartment itself was comfortable, clean, and well-equipped. Our host was incredibly attentive and made sure we had everything we needed for a smooth stay. Highly recommend this place!
Guest favorite

Home in West Town

4.85 out of 5 average rating, 310 reviews

Lux Urban 3BR/3BA Duplex + Parking!

McKenzieRating, 5 stars2 weeks ago
This space was a great fit for our work trip to Chicago. Lots of restaurants within walking distance. Hans was very helpful and responsive!
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.
Guest favorite

Apartment in Near South Side

5 out of 5 average rating, 26 reviews

Lux Loop Retreat: Amazing Views, Free Parking

JeremyRating, 5 stars2 months ago
This is our go to place when available for all the trade shows we do at McCormick. Everything is always perfect

Apartment in Bronzeville

4.45 out of 5 average rating, 20 reviews

Spacious 2bdm unit 15min to Dwtn

Helena ORating, 5 stars3 weeks 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 in Miller

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 🌟
Superhost

Apartment in The Loop

4.75 out of 5 average rating, 52 reviews

The Professional's Playground

Jura Rating, 5 stars4 weeks ago
Very nice place, location, wellness center beautiful, highly recommend this place to everyone !!
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!

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 stars3 weeks ago
Great apartment, very clean and well kept, we really enjoyed our stay!
Guest favorite

Apartment in Lincoln Park

4.87 out of 5 average rating, 183 reviews

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

KatherineRating, 5 stars2 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, 151 reviews

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

MeggieRating, 5 stars1 month ago
Jamie was an amazing host and the stay far exceeded expectations! From the detailed information about the city to the decor in the apartment, it was a stay to remember! Jamie was warm and accommodating as was the neighborhood and apartment! I hope to make this a yearly trip and stay here, with Jamie as my host I would always have a great time!
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 stars1 week 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, 498 reviews

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

CaitlinRating, 5 stars1 day ago
Great location next to the Logan Square stop, easily walkable and convenient from ORD.
Guest favorite

Apartment in Palos Hills

4.94 out of 5 average rating, 168 reviews

Aunt Linda's Apartment with a View in Palos

LizRating, 5 stars1 week 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

Apartment in The Loop

4.76 out of 5 average rating, 211 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

JasonRating, 5 stars6 days ago
Great location great host will stay here again.

Cabin in Union

4.5 out of 5 average rating, 4 reviews

Trailer- Rental Unit

KarissaRating, 5 stars18 months ago
Absolutely loved staying at Sylvia's! The camper is very conveniently located within the park - close to all the amenities and activities! Easy to access, beautiful grounds and a very peaceful stay for my family and I.

Apartment in The Loop

4.64 out of 5 average rating, 58 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!

Guest suite in Berwyn

4.67 out of 5 average rating, 42 reviews

Music Hot Spot’s Main Level

MichaelRating, 5 stars3 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.
Superhost

Home in Cedar Lake

4.84 out of 5 average rating, 83 reviews

Beautiful Home Oasis

SusanRating, 5 stars5 months ago
Beautiful house and surroundings. Great place to relax with a large family gathering. Lots for kids to do inside and out. We enjoyed the pool, fire pit, and sports areas. Hosts were very responsive and friendly.

Cabin in Union

4.69 out of 5 average rating, 71 reviews

Rustic Cabin

JustinRating, 5 stars4 months ago
Lovely hosts and easy check-in/out. Great inexpensive no-frills option. I would come back for sure!

Apartment in The Loop

4.77 out of 5 average rating, 231 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

EmmanuelRating, 5 stars1 week 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!

Quick stats about vacation rentals that are family-friendly in Woodridge

  • Total rentals

    20 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    690 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore