Kid-friendly vacation rentals in Wicker Park, Chicago

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Wicker Park, Chicago kid-friendly rentals

Kid-friendly house rentals

Guest favorite
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
4.89 out of 5 average rating, 132 reviews

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

DanielRating, 5 stars2 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.
Guest favorite
A well-lit entryway showcases a wooden staircase with elegant railing leading to upper levels. The dark front door contrasts with the light walls, while a stylish cabinet and framed photos add character to the space, inviting guests into the home.
Home in Roscoe Village
4.92 out of 5 average rating, 280 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

BrigidRating, 5 stars1 week ago
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.
Guest favorite
Home in Lake View
4.95 out of 5 average rating, 328 reviews

The Roscoe House near Wrigley Field

Institut Za Društvena IstraživanjaRating, 5 stars3 weeks ago
We were a party of five attending a scientific conference in Chicago's Loop. The accomodation was great as it is in the very quiet street and safe street but very close to all of the activities of Lakeview. Access to public transport is great. Overall we give highest recommendation for this great place to explore the great city of Chicago.
Top guest favorite
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 Lake View
4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars6 months ago
Lovely place in a good location.
Superhost
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 Bridgeport
4.7 out of 5 average rating, 50 reviews

Animal House near Sox stadium

KimRating, 5 stars2 weeks ago
Very nice home! Very nice host! Would definitely go again. Thank you so much for hosting us.
Top guest favorite
A spacious backyard is visible, featuring a well-maintained lawn surrounded by tall trees. The house stands in the background with a mix of brick and siding. A storage shed is positioned to one side, providing additional outdoor utility.
Home in Worth
5 out of 5 average rating, 15 reviews

3 x Queen Beds + Pull Out Sofa Bed - No Stairs !

Yi JianRating, 5 stars1 month ago
This place is amazing (like super!!!) ! It has everything we needed, and after a day out in the city, coming back to Bart's place just feels like such a relief. It’s cozy, comfortable, and really has a welcoming vibe. Couldn’t have asked for a better spot to unwind. Highly recommend!
Guest favorite
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
4.92 out of 5 average rating, 26 reviews

Bliss in Brookfield- 5BR, 3BA

DeanneRating, 5 stars1 week 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.
Top guest favorite
A bright living area is filled with comfortable seating, including two armchairs and a spacious sofa. A light area rug with a geometric pattern covers the floor. Natural light streams in through large windows adorned with wooden blinds, and a decorative tray sits on a plush ottoman.
Home in Lombard
5 out of 5 average rating, 25 reviews

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars5 days ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.

Kid-friendly apartment rentals

Guest favorite
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.
Apartment in Austin
4.95 out of 5 average rating, 185 reviews

Flexible Apt. for 8 by Oak Park-CHI

LindsayRating, 5 stars1 month ago
Exactly as pictured. Great location for families. Everything was well labeled and organized to find anything we needed. Everything you can possibly think of is provided- from spices to umbrellas. No issues with street parking and we could always find a spot close by. We would stay here again!
Top guest favorite
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.
Apartment in Lincoln Square
4.79 out of 5 average rating, 293 reviews

Cozy Garden-Subterranean Apartment

MorganRating, 5 stars6 days ago
Jenny went above and beyond! She was super communicative & very friendly. She even let me check in before checkin time, which I greatly appreciated. The apartment has literally everything you need. All the little details and small things you could want, are there. I would highly recommend staying here for a longer extent of time, as you would feel as if you’re in your own home.
Top guest favorite
A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.
Apartment in Avondale
4.98 out of 5 average rating, 105 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

JillRating, 5 stars1 month ago
Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.
Superhost
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.
Apartment in North Center
4.85 out of 5 average rating, 265 reviews

Family Friendly 3BR Duplex in Roscoe Village

LanRating, 5 stars2 weeks ago
John was a very kind and responsive host. Answered any questions we had very quickly. Home was exactly as pictured and described. Very comfortable place to stay. Everything was clean. Appreciated the family and kid friendliness of the home--not a lot of decorative items in reach that could be broken, no tables with sharp edges, low bed in the upper guest room that was easy to get in and out. Location was close to several restaurants and grocery stores, and not too far a drive from all the major tourist attractions.
Guest favorite
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
4.94 out of 5 average rating, 140 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

PreetiRating, 5 stars1 month ago
The place was clean and well kept .Letitia was very helpful and personable with local recommendations. I checked in late and there was a banana and apple waiting for me which really helped as it was too late for dinner but I was hungry. The kitchen is well equipped and the place is exactly as described. I had a wonderful stay.
Guest favorite
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.
Apartment in Hyde Park
4.84 out of 5 average rating, 122 reviews

Garden Apartment in captivating Hyde Park

ThongLengRating, 5 stars2 days 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. 😁
Guest favorite
Apartment in Evanston
4.85 out of 5 average rating, 247 reviews

Adorable 1BR apartment near Northwestern

JessicaRating, 5 stars1 month ago
We are happy with our stay at Liz’s airBNB. Liz was responsive and very accomodating to our specific check-in requests. Her place was spacious and easy to check-in. It had everything we needed. We were very grateful to easily find 2 street parking spots outside of her place. Her place was perfect for us as we were visiting Chicago but wanted some amentities that are not traditionally available in the city itself- i.e. parking spots, and easy in/out capability. I would recommend this airBNB and we would definitely stay with Liz again.
Guest favorite
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.
Apartment in Lincoln Square
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.

Kid-friendly condo rentals

Superhost
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
4.8 out of 5 average rating, 116 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

KindallRating, 5 stars3 months ago
The stay was nice and clean and very convenient location.
Guest favorite
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.
Condo in Bridgeport
4.95 out of 5 average rating, 126 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

BreannaRating, 5 stars2 weeks ago
John was very accommodating with my families needs. I loved that there was a washer and dryer in the unit. I would book this condo again in the future if available.
Guest favorite
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.
Condo in Bridgeport
4.89 out of 5 average rating, 111 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars5 days 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
Guest favorite
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.
Condo in Wrigleyville
4.82 out of 5 average rating, 342 reviews

Dream Condo steps from Wrigley Field!

ErinRating, 5 stars1 week ago
I cannot say enough great things about our stay. The location by Wrigley was perfect…amazing to step outside and be right at the park. Condo was spotless, check in and out was easy, beds super comfortable and the Cubs theme made it even more fun! Only wish we could stay longer and will definitely be back. Thank you for everything!
Guest favorite
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.
Condo in River North
4.98 out of 5 average rating, 131 reviews

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

SarahRating, 5 stars1 week ago
I highly recommend booking with Ketan! He was so helpful and gave us great recommendations. Check in/out was easy and I will definitely book this place if we have another big group in Chicago!
Guest favorite
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.
Condo in Chinatown
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.
Superhost
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.
Condo in Pullman
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
Guest favorite
A spacious living area features a modern sectional sofa in dark tones, accompanied by a light coffee table. Natural light filters through neatly arranged window coverings, illuminating the space. A unique hanging chair adds a touch of style, while sleek flooring complements the minimalist décor.
Condo in Mount Prospect
4.88 out of 5 average rating, 205 reviews

Lovely 3-bedroom condo, free parking, Unite 1

MiklosRating, 5 stars5 days ago
Had a great 3-night stay! The place was clean, cozy, and exactly as described. The host was super responsive and made everything easy. Would definitely stay again!

Quick stats about vacation rentals that are kid-friendly in Wicker Park, Chicago

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    3.1K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

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