Kid-friendly vacation rentals in Woodlawn, Chicago

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Woodlawn, Chicago

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A modern kitchen features sleek gray cabinetry and a spacious countertop. Stainless steel appliances, including a refrigerator and microwave, are visible. Natural light enters through a window above the sink, where a small flower arrangement is placed. The wood-inspired flooring complements the contemporary design.

Apartment in Joliet

4.95 out of 5 average rating, 203 reviews

*The Belltower Haven*Large*Family Friendly*Wi-Fi

Completely remodeled, spacious floor plan, in prime location. Everything is new. Free Wi-Fi (480Mbps) and private parking for 2 cars. Short walking distance to most anything! Near Chicago, The Rialto Theatre, Shopping Mall, Harrah's Casino, Hollywood Casino, Haley Mansion, Route 66 Raceway, Chicago Speedway, Autobahn Country Club. We have a large comfy King Size bed along with several Queen beds. Note: You must be 21 or older to book. Must provide a photo of your D.L. or State ID upon request.

Guest favorite

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.

Apartment in Lincoln Park

4.99 out of 5 average rating, 104 reviews

Lincoln Park Charm + On site Parking Included!

Come stay at this gorgeous, clean, renovated, top-floor apartment in beautiful Lincoln Park. The unit is located on a quiet block, yet close to everything. It includes a free on-site parking spot located directly behind the building and in-unit laundry! The unit is a walker's paradise, with so much nearby, including great shops and restaurants, the lake, the zoo, downtown, Wrigley Field, public transportation, Starbucks, Trader Joe’s, Whole Foods, a gourmet market, parks, playgrounds and more!

Guest favorite

A bright entryway features a white shelving unit adorned with a plant and a small decorative bottle. A wooden staircase is visible in the background, leading to the upper floor. Sunlight filters through the surrounding windows, creating a welcoming atmosphere.

Apartment in East Rogers Park

4.84 out of 5 average rating, 211 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

PRIVATE Entrance, One Bedroom Apt w/ LVG RM near Lake Michigan in beautiful, residential & diverse neighborhood. FREE on street PARKING, OR driveway spot for Addt fee. Sleeps up to 6. *It has a Kitchenette, Full Bath, WiFi, Cable TV, in unit W/D. Close to METRA TRAIN (1 block & 18 min to loop/city center), Bus Stop 1 block & the CTA "L" (elevated) Red Line to City 7 blocks away. Enjoy our proximity to Public Transit, Beaches, Loyola & NW Universities. Great for family, friends & kids.

Superhost

A welcoming living area features two bright yellow armchairs and a gray sofa, complemented by a textured rug. Large glass doors allow natural light to enter, while modern art adorns the wall. A sleek TV is positioned to one side, enhancing the cozy atmosphere.

Apartment in Lincoln Park

4.83 out of 5 average rating, 295 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

Nestled in a historic 1920s renovated hotel, this apartment retains charming Art Deco arches that add a touch of history to its modern comforts. Featuring warm timber floors that connect two cozy bedrooms with queen beds to a contemporary kitchen. Each room has a TV, and the kitchen is fully stocked for your convenience. With two full bathrooms and barrier-free one-floor access, this space combines old-world charm with modern living in the vibrant heart of Lincoln Park, close to the Lakefront.

Top guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 235 reviews

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

A Wonderful 2 bedroom Airbnb in the Superhot Lincoln Park neighborhood on a block where homes sell from 5 million to 12.5 million dollars. The apartment was totally renovated adding new furniture, 50-inch High-Definition Flatscreen in the Livingroom, a fully stocked kitchen, superfast wifi, parking space, rooftop deck, Patio, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop. Pack-in-play, highchair, kids. Millennium Pk, Navy Pier, Mag Mile, Museum.

Guest favorite

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

4.96 out of 5 average rating, 110 reviews

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

Superhost

The kitchen features dark wooden cabinets and a polished marble dining table with four padded chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, along with a stovetop and oven. Natural light filters in through a nearby window.

Apartment in Oak Park

4.75 out of 5 average rating, 151 reviews

1BR Apartment - Walk to Shops - Downtown OAK PARK

Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 min drive to grocery stores & shopping - 20 min drive to Downtown Chicago Enjoy the historic neighborhood and see Frank Lloyd architecture nearby. ➢ Everything is sanitized/washed/cleaned after every guest ➢ Fast, Dedicated Wifi ➢ 2 Smart TVs (Living Room, Bedroom) ➢ Fully equipped + stocked kitchen / bathroom ➢ Pack 'n Play

Guest favorite

Apartment in Logan Square

4.95 out of 5 average rating, 693 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Guest favorite

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.

Condo in Wicker Park

4.83 out of 5 average rating, 339 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Superhost

A cozy living area is furnished with two grey sofas adorned with black-and-white checkered pillows. Red chairs are positioned near a wooden side table. A sideboard with magazines adds a touch of practicality, while three windows provide natural light, framed by white blinds.

Apartment in Logan Square

4.86 out of 5 average rating, 125 reviews

Bingham 2/2

Short walk to Blue Line nestled on a block with easy access to Bucktown & Logan Square. Second floor duplex with a den/third bedroom on main floor. All sleeping spaces have doors. Great location for business downtown, Cubs game, parents weekend at most of our universities. Easy walk to some of Chicago's hottest restaurants, bars, breweries and coffee shops. Plus, easy access to beautiful parks. Quiet family neighborhood.

Top guest favorite

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.

Apartment in Lincoln Square

4.96 out of 5 average rating, 369 reviews

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

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Superhost

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

4.83 out of 5 average rating, 178 reviews

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

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!