Family-friendly holiday rentals in Oak Brook

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Oak Brook family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in West Town
4.85 out of 5 average rating, 319 reviews

Lux Urban 3BR/3BA Duplex + Parking!

MariaRating, 5 stars1 week ago
This was our third time staying at this property and we’re looking forward to stay again next time we’re in Chicago. Hans was very responsive and easy to communicate with. The place is spacious and comfortable. It’s quite, full equipped kitchen and nice backyard. I highly recommend this place
Home in Miller
4.55 out of 5 average rating, 164 reviews

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

JohnRating, 5 stars2 months ago
This was a lovely cottage and a great getaway from a busy Chicago life. We only spent a couple nights but we brought my dog and we just wanted to chill for a bit. Soaking in the hot tub was a must! The backyard was completely fenced in so my dog could roam and investigate while we enjoyed the hot tub under strings of yard lights, creating a peaceful vibe. Loved it! We cooked a lot (inside) since the weather was cool and windy and the well-stocked kitchen was much appreciated. Great coffee machine (bring your own coffee!) and dishwasher. They came in very handy. Comfortable beds, clean linens, adjustable thermostat with easy instructions, extra blankets and pillows... all you'll need to feel at home. Thank you for a great time and we can't wait to come back. Next time we're bringing our friends!
Home in Miller
4.56 out of 5 average rating, 133 reviews

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

DonnaRating, 5 stars1 month ago
Everything was good just washing machine was not working and dish washer wasn’t operating good and there was enough toiletries
Loft in Garfield Ridge
4.76 out of 5 average rating, 88 reviews

Super Paradise Chicago

KaileyRating, 5 stars64 months ago
Great place to stay! Fausto was very responsive and left treats/drink in the fridge for us. He was a wonderful host and would go back!
Top Guest favourite
Condo in Logan Square
4.98 out of 5 average rating, 279 reviews

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

JudyRating, 5 stars1 week ago
We had a great stay in Logan Square. The location has walkable access to the Blue Line making downtown easy. While this is a lower level unit, this does not feel at all like your standard “garden level”. It was full of windows and bright. Furniture was very comfortable. Bathrooms well appointed with amazing shower pressure. The bedroom is so quiet you get a great nights sleep. Bonus points for lamps on BOTH sides of the bed. The closet had high quality hangers plus good storage. The kitchen has everything needed for cooking or for storing leftovers from fabulous restaurants in area. The garage is a great bonus. Our young adult children live in the area and it was prefect for them to come over, hang out and visit with us. We spent time outside in the garden area with the fire table. Bryan was very responsive and helpful through our four-night stay. We will be back!
Apartment in Bronzeville
4.33 out of 5 average rating, 27 reviews

Spacious 2bdm unit 15min to Dwtn

HeavenaRating, 5 stars1 month ago
i loved this airbnb, great spot if you just want to explore chicago. max was super quick with responses and helpful with any questions i had.
Home in Miller
4.67 out of 5 average rating, 94 reviews

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

ИванRating, 5 stars2 weeks ago
The excellent host explained everything in advance, agreed on all the nuances. We had a great time with a group of 12 people. In my experience, I recommend it.
Condo in Andersonville
4.89 out of 5 average rating, 9 reviews

Bright and Beautiful Penthouse - Close to the lake

GautamRating, 5 stars35 months ago
We had a great stay at Delphine's place in Uptown. The location is excellent, being on a tree-lined street, but very close to the Red Line, the Broadway bus, Andersonville, Little Asia, grocery stores and more. As we had a little kid, being right on top of the little park downstairs was also very convenient. On the flipside, it can get noisy in the summer with lots of kids/playgroups coming there, but as parents, we didn't mind. Delphine herself was very quick to respond via Whatsapp to all our queries before and during our stay. One thing to keep in mind at her place is that you are very much living in their home. If you are looking for an apartment that is only intended for guests, this is not it. While it is plenty big as a 2BR/2BA, it is full of stuff, furniture, photos, books, toys, etc. They have made a very nice office space in the main living area, but the drawback is that the living area is now very cramped. The main bedroom has 2 queen size beds in it, which is a bit weird, so we just ended up using one bed to keep our clothes on. The other bedroom with bunk beds is excellent for kids and more spacious. So overall, a great place and a great stay, and especially good if you are a couple with 1 or 2 kids. Just a bit cramped and crowded with stuff. We stayed for 2 weeks.

Family- and pet-friendly home rentals

Guest favourite
Apartment in Roscoe Village
4.96 out of 5 average rating, 303 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

LetaRating, 5 stars3 weeks ago
I would highly recommend Dennis' place. It was super clean. Had all the amenities you may want. Close to a lot of places yet quiet. We felt totally safe and loved the balcony.
Guest favourite
Apartment in Logan Square
4.9 out of 5 average rating, 405 reviews

Sunny Logan Square Artists' home

KatyRating, 5 stars3 weeks ago
We loved our stay at Kyle’s place - it was decorated SO cute (I went with two girlfriends and I’m pretty sure we all squealed with joy when we first opened the door). The location was perfect - just a quick walk to all the shops and restaurants Logan Square had to offer - and to public transportation (which we used the whole time in Chicago). The neighborhood was very peaceful and quiet; we all felt very safe. When I come back to Chicago, I will absolutely be staying here again. Thanks for sharing your space with us, Kyle! We loved it! (Side note: you gave me so many ideas for house decor, your style is impeccable!)
Top Guest favourite
Home in Uptown
4.9 out of 5 average rating, 367 reviews

Private 3rd Floor Apartment

RickRating, 5 stars1 month ago
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.
Top Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 295 reviews

Stylish Studio in Historic Logan Square

AlyssaRating, 5 stars6 days ago
⭐️⭐️⭐️⭐️⭐️ 5/5 We had a wonderful stay! The space was clean, cozy, and exactly as described in the listing. The host was super responsive and made check-in seamless. We especially appreciated the little touches and great local recommendations. The neighborhood felt safe and was close to everything we needed. Would absolutely stay here again and recommend it to anyone visiting the area!
Top Guest favourite
Guest suite in Portage Park
4.95 out of 5 average rating, 164 reviews

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

TerenieRating, 5 stars1 week ago
Jamie was a really amazing host! She was friendly, helpful, caring and went over and beyond to make sure me and my kids were comfortable and had everything we need. Gave us lots of great recommendations to restaurants and as a first timer in Chicago she made sure I was aware of the traffic and other helpful information! My kids LOVE her she was vey nice, patient and gentle with them. Kid friendly house/area VERY quiet. The beds are the BEST after a long day of traveling very comfortable. The place was beautiful very nice decor and nicely maintained. We will definitely be staying here on our next visit to Chicago.
Top Guest favourite
Apartment in Logan Square
4.95 out of 5 average rating, 519 reviews

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

JoshuaRating, 5 stars4 days ago
Our family loved our weeklong stay. Perfectly located with beautiful wood details and stocked with games for the kids, it was charming and convenient. Paul and Sarah were very helpful and we had everything we needed. We would all be happy to stay here again.
Guest favourite
Apartment in Logan Square
4.96 out of 5 average rating, 126 reviews

Garden Unit Getaway-Bucktown

JasonRating, 5 stars3 days ago
Keith's place was exactly what we were looking for! We could walk from the Blue Line (which we took to/from O'Hare and to/from the Loop), and within a mile or so there were a ton of fun shops and dining options. We were there in the midst of a heat wave, and the basement apartment + AC unit keep us cool and comfortable the entire time.
Guest favourite
Condo in Evanston
4.77 out of 5 average rating, 643 reviews

Spacious Evanston Unit - Walk to Northwestern U

JenniferRating, 5 stars6 days ago
Third time's the charm -- we are repeat visitors so my dog and I felt right at home in Yvonne's place and neighborhood near Northwestern. Everything is clean and comfortable. Communication is great. Will stay there again if available.

Family-friendly home rentals with a pool

Apartment in The Loop
4.77 out of 5 average rating, 223 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

JaredRating, 5 stars3 weeks ago
The location is perfect for getting to any part of Chicago. It's within walking distance of endless activities, and within one to two blocks of multiple "L" and subway lines that will take you anywhere. You are staying in the middle of the city, so you will hear the train and sirens throughout the night; however, the host provides disposable ear plugs which were very helpful. I had no problem sleeping throughout the night. Front desk staff is always friendly. The host is very responsive, and courteous. Washer and dryer in unit helped me with not having to pack as many cloths for my trip. Everything was spotless upon arrival. Would absolutely stay here again.
Top Guest favourite
Apartment in Near South Side
5 out of 5 average rating, 35 reviews

Lux Loop Retreat: Amazing Views, Free Parking

JanRating, 5 stars1 week ago
Run, don't walk, to book this location for your Chicago stay. The view of the Chicago skyline is perfect, even better than if you stayed in Downtown itself, sometimes all you see is the wall of another building and no view. The instructions how to get there are very clear, if you're a little intimidated like I was about going to a big city never fear. The instructions are clear, easy to follow, and transit is close by to take you wherever you want to go. Overall great trip, thank you!
Place to stay in Berwyn

Beat-Town Flex Stays

KimberlyRating, 5 stars25 months ago
Second stay. Rose accomplishes blending comfortable clean accommodations with a relaxed and folksy vibe. Recommended!
Cabin in Union
4.5 out of 5 average rating, 4 reviews

Trailer- Rental Unit

KarissaRating, 5 stars23 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.
Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars10 months ago
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!
Guest suite in Berwyn
4.69 out of 5 average rating, 45 reviews

Music Hot Spot’s Main Level

MylesRating, 5 stars1 week ago
Rosie was the perfect host. Before our arrival. Lots of recommendations to do and see off at the use of her bikes across to use at no charge. On arrival offered to pick us up at the airport but we were delayed. During our stay of six days, Rosie and her husband were always on hand to help with recommendations what to do and see About a 30 minute cab drive from the airport and 30 minutes downtown or 10 minute walk to the train and 30 to 40 minute ride which is no stress It was clean and comfortable the kitchen had everything you needed
Guest favourite
Apartment in Near South Side
4.88 out of 5 average rating, 205 reviews

Stunning Panoramic Chicago Views & Free Parking

KariRating, 5 stars1 week ago
We knew from the photos on the listing that the view was spectacular and that the apartment was nice. We were not prepared for all of the extra, thoughtful touches that were part of this property. It was like staying in a spa! The lavender oil infused warm washcloths, towel warmer, and bathrobes were unexpected and much appreciated! Thank you, Amanda, for having us at your property. We'll be back.
Cabin in Union
4.71 out of 5 average rating, 82 reviews

Rustic Cabin

MaryRating, 5 stars1 week ago
Just what I wanted, a nice basic cabin to camp with my dogs. Lots of family activities and a great little dog park and paths to walk the dogs without disturbing other campers. Good bathrooms and showers. Firewood delivered to your camp site. I’ll be back whenever I need a little getaway 🙂.

Quick stats about holiday rentals that are family-friendly in Oak Brook

  • Total rentals

    10 properties

  • Nightly prices starting at

    $233 NZD before taxes and fees

  • Total number of reviews

    440 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore