Kid-friendly vacation rentals in Downtown Chicago

The spacious living area features large windows that provide ample natural light. A comfortable gray sofa is complemented by two dark chairs with wooden legs. A wooden coffee table sits in the center, adorned with a small plant. A television is mounted on the wall opposite.

4.99 out of 5 average rating, 103 reviews

Lincoln Park Charm + On site Parking Included!

ForrestRating, 5 stars1 month ago

A great place for our family of 4 for a week-long stay. Location was great - very walkable, quiet street, easy onsite parking, close to lots of good restaurants and the L (but not too close). Condo was clean and as expected from the description. Would stay again!

4.98 out of 5 average rating, 235 reviews

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

AnneRating, 5 stars1 day 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

A spacious backyard is depicted, featuring a lush green lawn and a mix of trees and bushes. A patio area with a dining table is visible, providing an opportunity for outdoor meals. The fenced yard offers privacy and a tranquil space for relaxation.

Home in Elmhurst

Elmhurst NEW - Super Clean Modern Farmhouse!

AndrésRating, 5 stars2 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.

4.95 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.

The living area features a plush, gray sofa paired with a deep blue accent chair. A light-colored coffee table rests on a patterned rug, while warm lighting is provided by wall-mounted fixtures. A small bookshelf and decorative items add a personal touch to the space.

4.83 out of 5 average rating, 339 reviews

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.

A bright dining area features a round blue table surrounded by four matching chairs. Natural light enters through several windows, with leafy greenery visible outside. A stylish clock hangs on the wall, adding a functional element to the cheerful space.

4.96 out of 5 average rating, 369 reviews

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

TannerRating, 5 stars2 days 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!

4.83 out of 5 average rating, 178 reviews

A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.

Apartment in Evanston

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

SkylarRating, 5 stars3 weeks ago

Craig was extremely nice and accommodating when it came to my birthday weekend. He responds quickly to all questions asked and makes sure we’re comfortable at all times. This home was clean, accurately described, and had the perfect “home feeling”. Overall, when visiting the area I will be booking here again !

Vacation rentals for every style

Get the amount of space that is right for you

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A space thats all yours, with room for everyone

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Convenient locations with everyday essentials

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Popular amenities for Downtown Chicago kid-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Kid-friendly house rentals

4.77 out of 5 average rating, 26 reviews

A spacious backyard features a circular stone fire pit surrounded by six blue adirondack chairs. In the background, a gazebo provides shade, while a well-maintained lawn with green grass and trees offers a relaxing outdoor space.

Home in Roselle

Game Room | Fire Pit | Full Gym

AlexandraRating, 5 stars2 days ago

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

4.89 out of 5 average rating, 132 reviews

A single-story house features a welcoming entrance with a front step and decorative wreath. Inside, cozy sleeping areas include both a queen bed and twin bunk beds. A smart TV displays a cityscape, while a dining table with six chairs is ready for meals.

Home in Lombard

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

DanielRating, 5 stars4 weeks ago

Great place to Spend the night or even a week. Our fight to Miami got canceled and his place was the perfect place for our family of 5 to spend the night. Friendly and responsive would definitely recommend to anyone looking for a place to stay in Chicago.

4.93 out of 5 average rating, 153 reviews

The exterior of the duplex showcases a charming facade with large windows and a distinctive oval entrance. A well-maintained garden, framed by a black iron fence, adds a touch of greenery to the welcoming entrance. Stairs lead up to the front door, enhancing accessibility.

Home in Chicago

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars6 months ago

Lovely place in a good location.

4.72 out of 5 average rating, 53 reviews

A bright living space features an orange sectional sofa adorned with decorative cushions. Colorful wall art creates visual interest, while a small kitchenette with a bar height table and stools is visible. Natural light filters in through large windows, complementing the warm wood floors.

Home in Chicago

Animal House near Sox stadium

ChristineRating, 5 stars4 days ago

Thanks so much for everything! I have a reactive dog that has never been left in a doggy daycare, and Miranda helped me experiment to find the right fit for him. I was able to attend my conference and I am very grateful. Great place and great host!! <3

4.9 out of 5 average rating, 99 reviews

An air hockey table occupies the center of the game room, featuring a smooth white playing surface with red markings. Two orange paddles and pucks are positioned at either end. A retro yellow chair and a small table are visible in the corner, with natural light coming through large windows.

Home in Downers Grove

Games, Grounds, Goodness in DG

EileenRating, 5 stars1 week ago

Kathleen is a very sweet and responsive host! The house was in a quiet and nice neighborhood. Wish we had more time to enjoy the games and better weather to enjoy the yard. Would definitely stay again!

4.93 out of 5 average rating, 27 reviews

A finished basement features a spacious seating area, including a comfortable sectional sofa and a coffee table. A dining table accommodates six, and a television is positioned on the wall. Recessed lighting enhances the bright, open atmosphere.

Home in Brookfield

Bliss in Brookfield- 5BR, 3BA

DeanneRating, 5 stars3 weeks ago

Nice to have a spacious place to stay with family. Our toddlers were in heaven in the basement toy/family room. Bedrooms and closets were spacious as well. Communication with host was easy with prompt responses. We would stay at this property again.

5 out of 5 average rating, 11 reviews

A spacious living area features a modern television mounted on a light-colored wall, flanked by a comfortable sofa set. A neutral coffee table sits centrally, while soft natural light enhances the inviting atmosphere through large windows. A dining area is visible in the background.

Home in Romeoville

Rejuvenate: 4BR, fenced yard

Fredy JavierRating, 5 stars5 months ago

The only thing I didn’t like was the smart lock due to having to download an app and creating an account , there is not an exterior pic of the place and the floor was to noise when walking, I would wake up in the middle of the night from my roommates waking up to the toilet or early in the morning . But everything else was perfect.

5 out of 5 average rating, 3 reviews

The exterior of a two-story home is displayed, featuring a brick and siding facade. A driveway leads to a garage with a closed door. Lush landscaping includes various plants and flowers, while a tall fence provides privacy. The sky is partly cloudy.

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.

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Kid-friendly apartment rentals

An inviting dining area features a simple wooden table accompanied by two benches and a chair. A cozy seating arrangement includes a sofa and coffee table, framed by large windows dressed in light curtains. A ceiling fan and decorative accents add to the space.

4.72 out of 5 average rating, 117 reviews

The Biddle House (#1)

SitaRating, 5 stars3 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!

The living area displays a spacious futon-style sofa adorned with red cushions, accompanied by a wooden rocking chair. A dark coffee table sits centrally, with a TV positioned on a cabinet. The carpeted floor enhances the cozy ambiance, while recessed lighting brightens the space.

4.95 out of 5 average rating, 187 reviews

Flexible Apt. for 8 by Oak Park-CHI

WeikunRating, 5 stars2 days 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!

The living area is furnished with a striped sofa and a colorful accent chair, complemented by a small side table and a lamp. A neat dresser and a glimpse of the kitchen area are visible. A green area rug enhances the cozy atmosphere.

4.79 out of 5 average rating, 295 reviews

Cozy Garden-Subterranean Apartment

NikkiRating, 5 stars2 days 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!

A comfortable living area is fitted with a dark leather sofa and two patterned armchairs. Natural light enters through a large window, adorned with turquoise curtains. A round glass coffee table sits at the center, reflecting soft lighting from two nearby lamps.

4.85 out of 5 average rating, 267 reviews

Family Friendly 3BR Duplex in Roscoe Village

KellyRating, 5 stars2 weeks ago

It was really good. It's an older building so it had old-building problems (creeky floors kinda thing). Other than that it was perfect for our family of four: enough room to do our own thing, enough room to be together.

4.94 out of 5 average rating, 141 reviews

A cozy seating area is highlighted by a plush sofa, complemented by a textured throw draped over the arm. A vintage-inspired painting hangs above, depicting a pier, while a lamp and a low wooden console table enhance the warm atmosphere. A vibrant area rug adds color beneath.

Apartment in Evanston

Vintage sunlit 2.5 BR apt. Perfect for families!

TomRating, 5 stars2 days 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.

A cozy living area features a red couch and a plaid armchair, providing comfortable seating options. A small table stands beside a lamp, illuminating the space softly. Foliage adds a touch of nature, and large windows allow natural light into the room while being partially covered.

4.83 out of 5 average rating, 123 reviews

Garden Apartment in captivating Hyde Park

ThongLengRating, 5 stars1 week 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 stars1 week ago

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

A well-lit studio apartment features a spacious bed and a comfortable seating area with a sofa and coffee table. Natural light fills the room through multiple windows, and a collection of decorative pillows adds a splash of color. A wooden dresser and striped rug enhance the interior.

4.93 out of 5 average rating, 218 reviews

Spacious, light-drenched studio-private entrance!

StasiaRating, 5 stars2 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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Kid-friendly condo rentals

4.8 out of 5 average rating, 117 reviews

A living area features a dark sofa adorned with cushions in blue and brown tones. A glass side table stands beside the sofa. Double doors lead to a balcony, while a window with blinds allows natural light to enter the space. Two closet doors are visible.

Condo in Evergreen Park

Evergreen Park Condo with balcony and Jacuzzi tub

DRating, 5 stars1 month ago

Nice. Clean. Responsive host.

A cozy living area features a gray sectional sofa adorned with patterned cushions. A white coffee table sits on a soft area rug, while a vase of flowers adds a touch of elegance. An open kitchen with wooden cabinets is visible in the background.

4.95 out of 5 average rating, 128 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

AudreyRating, 5 stars1 week 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.

A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.

4.89 out of 5 average rating, 112 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars2 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

A view overlooking a vibrant urban landscape featuring Wrigley Field in the background. Rooftops, utility units, and modern buildings create an interesting skyline. The image captures the spirit of the neighborhood, with hints of greenery and construction highlighting the area's dynamic atmosphere.

4.83 out of 5 average rating, 343 reviews

Dream Condo steps from Wrigley Field!

AnitaRating, 5 stars6 days ago

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

A spacious living area is arranged with a large sectional sofa facing a wall-mounted television. A decorative area rug lies beneath a low coffee table. Adjacent, a dining area features a wooden table surrounded by chairs, with an open kitchen visible in the background.

4.99 out of 5 average rating, 134 reviews

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

JoelRating, 5 stars5 days 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!

A modern living area features a black leather sectional sofa adorned with colorful accent pillows. A sleek coffee table sits in front, and a dining table with white chairs is positioned nearby. Natural light streams through large windows, highlighting the neutral color palette.

4.92 out of 5 average rating, 120 reviews

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

TehranRating, 5 stars1 month ago

Very great for a large group.

A living area features a white upholstered sofa and a contemporary glass coffee table on a geometric area rug. Natural light filters through multiple windows, while a stylish light fixture is mounted on the ceiling, creating a bright and welcoming atmosphere.

4.83 out of 5 average rating, 137 reviews

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