Kid-friendly holiday rentals in Near North Side, Chicago

4.84 out of 5 average rating, 100 reviews

Home in Logan Square

California Cottage/4br prime location Logan Square

JeniRating, 5 stars3 weeks ago

Daniel’s house was perfect for what we needed. Seven adult women were comfortable and enjoyed the open table space. Bathrooms in basement and main level were clean, and plenty of linens and towels were supplied for the three nights we were there. Nice location for easy pickups and stores with delivery nearby for quick groceries. Also check out Diversey House nearby - great food and drinks! Thanks for a great weekend getaway!

Apartment in Lincoln Park

4.98 out of 5 average rating, 236 reviews

Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck

AnneRating, 5 stars6 days ago

We loved everything about that apartment. Great neighbourhood, easy to get around, shops and restaurants nearby - amazing. The place itself is beautiful - very clean and friendly. We liked the beds…very comfortable mattresses. If I ever come back to Chicago I would choose the same apartment..no question!

4.96 out of 5 average rating, 110 reviews

Home in Elmhurst

Elmhurst NEW - Super Clean Modern Farmhouse!

AndrésRating, 5 stars3 weeks ago

Incredible place to stay. Cherrie was very helpful throughout our stay and cannot recommend this place enough. It’s super peaceful and private. It’s a 25 minute drive to Chicago and other surroundings. Beds are very comfortable. Kitchen is a dream to use. Will definitely come back another time.

4.9 out of 5 average rating, 101 reviews

Home in Downers Grove

Games, Grounds, Goodness in DG

David SRating, 5 stars5 days ago

The moment we stepped into the house it felt like a home. Very clean and cozy. We had a little trouble with the keypad but that was taken care of very quickly. Quick response from the host. Was able to get a hold of them when we had some questions. The kids loved the game room. Definitely would recommend and stay again if needed!!

Apartment in Logan Square

4.95 out of 5 average rating, 693 reviews

Best in Chicago, private, amazing garden space

NatalieRating, 5 stars1 month ago

Meighan's apartment is cute and thoughtfully, stylishly laid out. From the living room, bedrooms, bathroom, kitchen/dining area, and lovely shared garden area, this was a really lovely space that was walkable, very homey, and refreshing. I commuted to downtown each day, and the walk to take the blue line was easy and close by. Meighan's bulletin board recommendations for nearby restaurants was great. I was able to find and use the 606 jogging path nearby thanks to a bulletin board brochure. Meighan was kind and welcoming to my dogs and me and it was so great to be able to bring them with me. Meighan responded quickly to my texts. Meighan provides a filtered water pitcher in the refrigerator which I recommend using for you and your pets. My dog got the runs a few days into our stay and he has a sensitive stomach when it comes to water and old pipes. As soon as I started giving my dog filtered water his issues cleared up immediately, which also alerted me to drink the filtered water.

4.83 out of 5 average rating, 339 reviews

Condo in Wicker Park

Lively Wicker Park 2br, Steps to Damen Blue Line

AmberRating, 5 stars1 month ago

Great place with a great location, central to all things in Wicker Park and Bucktown. Easy to get downtown via the blue line and walkable to all bus stops. Matched the photos and description and Vanessa and Charlie were very communicative and helpful.

Apartment in Lincoln Square

4.96 out of 5 average rating, 369 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

TannerRating, 5 stars1 week ago

Marla & James were incredible hosts! We had an absolutely great time - the neighborhood and airbnb space were perfect for our family of a toddler and two dogs we brought with us. James and Marla had plenty of games and accommodations for our toddler that he really enjoyed the space as well! Thanks again you two!

Guest suite in Naperville

4.95 out of 5 average rating, 414 reviews

Cozy Lakeview Studio with Private Access

YuRating, 5 stars1 week ago

Thank you so much for the wonderful stay! I was so glad to have chosen your place! Also, it was wonderful meeting you all! I had a nice time chatting with you! I hope to be back with my husband next! Happy Spring! Thanks, again!

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

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A space that's all yours, with room for everyone

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

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Wi-Fi

Pool

Free parking on premises

Air conditioning

Child-friendly house rentals

4.77 out of 5 average rating, 26 reviews

Home in Roselle

Game Room | Fire Pit | Full Gym

AlexandraRating, 5 stars1 week ago

Great stay. Was perfect for our 4 adults and 2 kids

4.89 out of 5 average rating, 133 reviews

Home in Lombard

Comfy Home w Access to Major Roads/Hwys, Huge Yard

ShelleyRating, 5 stars2 weeks ago

Wonderful cozy house in a nice peaceful and quiet neighborhood, conveniently located near major highways and easy commute to my company’s headquarters. My family had a nice time living in Lombard for the week.

4.93 out of 5 average rating, 153 reviews

Home in Lake View

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars6 months ago

Lovely place in a good location.

4.93 out of 5 average rating, 28 reviews

Home in Brookfield

Bliss in Brookfield- 5BR, 3BA

TaiquitiaRating, 5 stars1 week ago

My stay was wonderful everything was nice. Communication was outstanding.

4.87 out of 5 average rating, 46 reviews

Home in Gary

The Blue House: Family Retreat

MichaelRating, 5 stars1 day ago

We enjoyed our stay at this house . She was very responsive and she made good use of space in the house to accommodate a family. Would recommend to anyone.

4.91 out of 5 average rating, 34 reviews

Home in Wood Dale

Cozy 2 bedroom home in a wonderful neighborhood.

LinhRating, 5 stars5 months ago

I think this was my fav Airbnb yet. Convenient, very clean and a great kitchen! My dog enjoyed the backyard and the neighborhood was nice. I misplaced the house keys and Joanna responded immediately and had a solution! Thank you so much for that!!!! Would love to stay again when we visit family next year.

5 out of 5 average rating, 3 reviews

Home in Homer Glen

4 bedroom home rental in quiet neighborhood

LoriRating, 5 stars71 months ago

Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.

4.85 out of 5 average rating, 107 reviews

Home in Chicago

Peaceful Family Home near Downtown, MDW, Free Park

EmalieRating, 5 stars2 months ago

Safe location in a neighborhood. Clean and hosts were responsive and helpful. Not too far from downtown

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Kid-Friendly apartment rentals

Apartment in Lincoln Park

4.72 out of 5 average rating, 117 reviews

The Biddle House (#1)

SitaRating, 5 stars4 months ago

We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!

4.95 out of 5 average rating, 187 reviews

Apartment in Austin

Flexible Apt. for 8 by Oak Park-CHI

WeikunRating, 5 stars1 week ago

We had a wonderful stay! Lois was very responsive and made everything easy from start to finish. The house was cozy, clean, and well-equipped with everything we needed. Parking was super convenient, and the neighborhood felt safe and quiet. It was a perfect spot to relax after a day out. Highly recommend!

Apartment in Lincoln Square

4.79 out of 5 average rating, 296 reviews

Cozy Garden-Subterranean Apartment

NikkiRating, 5 stars1 week ago

This is the perfect place for a cozy Chicago getaway, very clean, peaceful, great location, and probably the most well-stocked Airbnb I’ve ever stayed in. Jenny is very friendly and responsive. I would stay here again in a heartbeat!

Apartment in Lincoln Park

4.83 out of 5 average rating, 295 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

CatherineRating, 5 stars1 week ago

Jessica’s place was great and perfect jumping off point for my family attending my brother’s wedding and other festivities.

4.94 out of 5 average rating, 141 reviews

Apartment in Evanston

Vintage sunlit 2.5 BR apt. Perfect for families!

TomRating, 5 stars1 week ago

I enjoyed my stay at Letitia's place. I was traveling between the city and northern burbs, and Letitia's place provided a nice centralized location with easy access to both. Letitia's place is clean, charming, and comfortable. Letitia responded quickly to any questions. I recommend this as a comfortable place to explore the greater Chicagoland area.

4.83 out of 5 average rating, 124 reviews

Apartment in Hyde Park

Garden Apartment in captivating Hyde Park

ThongLengRating, 5 stars2 weeks ago

Nice location with nearby supermarket, cafes and restaurants. The nearby busstop to go downtown is also very nice and near. Great apartment with all the necessary amenities for short stay. 😁

4.85 out of 5 average rating, 248 reviews

Apartment in Evanston

Adorable 1BR apartment near Northwestern

TaraRating, 5 stars2 weeks ago

Nice place to stay in a good neighborhood! Would stay here again, thank you!

Apartment in Lincoln Square

4.93 out of 5 average rating, 218 reviews

Spacious, light-drenched studio-private entrance!

StasiaRating, 5 stars3 months ago

We had the privilege of a long stay at Wendy’s studio. The space is SO sweet and cozy, and the layout feels larger than it appears in photos—there is a fair amount of built-in separation between each area. The kitchen is well-equipped for actual cooking, the bed is heavenly, and the shower feels like a spa! It is an incredible retreat in a residential Chicago neighborhood that is a bit tucked away while still being accessible. What a lovingly crafted space and considerate host! We hope to stay again and will absolutely recommend to friends and family.

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Child-Friendly Holiday Condos

4.8 out of 5 average rating, 117 reviews

Condo in Evergreen Park

Evergreen Park Condo with balcony and Jacuzzi tub

DRating, 5 stars2 months ago

Nice. Clean. Responsive host.

4.95 out of 5 average rating, 128 reviews

Condo in Bridgeport

Entire 3Bed/2Bath Condo Near McCormick & Metro

AudreyRating, 5 stars2 weeks ago

We enjoyed our stay. John works hard to offer the best experience to his guests. The place was super clean and welcoming. Photos are matching. Close to everything with UBER. Some restaurants are located in the block. I recommend this appartement.

4.89 out of 5 average rating, 112 reviews

Condo in Bridgeport

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars3 weeks ago

Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend

4.83 out of 5 average rating, 344 reviews

Condo in Wrigleyville

Dream Condo steps from Wrigley Field!

AnitaRating, 5 stars1 week ago

I would definitely stay here again! Walking distance from Wrigleyville bars, restaurants and stadium. Comfortable, clean and quiet.

4.99 out of 5 average rating, 134 reviews

Condo in River North

Luxurious River North 3BR/2BA- Free Onsite Parking

JoelRating, 5 stars1 week ago

Neel went above and beyond for my family and I during our stay. The unit was quiet, fun to hang out in, extremely clean, great layout for a family, very convenient parking, and quiet. I would highly recommend staying here! Thank you Neel!

4.92 out of 5 average rating, 120 reviews

Condo in Chinatown

1 #33 - 4 Bdrm Condo - McCormick Place, Chinatown

TehranRating, 5 stars1 month ago

Very great for a large group.

4.83 out of 5 average rating, 137 reviews

Condo in Pullman

Gamers Getaway 20 minutes from downtown

KaylinRating, 5 stars1 month ago

Loved The Space! Everything Was Perfect! Any Problems Or Any Questions Daniel Was Very Helpful! THANK YOU DANIEL