Family-friendly vacation rentals in Oak Brook

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Oak Brook

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A cozy living area features a plush green sofa adorned with patterned throw pillows. A textured rug covers the floor, while a wooden staircase leads to the lofted sleeping area. Natural light filters through the window, illuminating the space.

Guest suite in West Town

4.96 out of 5 average rating, 338 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favorite

A spacious living room features large windows draped with light curtains, allowing natural light to fill the space. A comfortable sofa and loveseat are positioned around a decorative area rug, with a television mounted on a cabinet. A rocking chair adds additional seating.

Apartment in Evanston

4.94 out of 5 average rating, 140 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 18 min walk for trains to city, 5 min drive to lake. Wifi

Guest favorite

The entrance to the vintage home is framed by lush greenery, showcasing a well-maintained front yard. A charming porch features seating near the steps, inviting relaxation. Large windows provide plenty of natural light, enhancing the home's welcoming appearance.

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.

Top guest favorite

A living room features a large bay window with multiple panes, offering a view of greenery outside. A comfortable sofa is adorned with colorful pillows, complemented by a contemporary armchair and side tables. Warm light is provided by a nearby lamp.

Apartment in West Lake View

4.98 out of 5 average rating, 244 reviews

North Side Near Wrigley Lakeview Walk Everywhere!!

Located on a beautiful tree lined street one block from the thriving Southport Corridor, one of the hottest neighborhoods in Chicago. You'll love the convenience of being just steps from the Southport Brown Line "L" Stop, you can see the City without ever needing to drive. Steps to outstanding restaurants, bars and shopping. Going to Wrigley Field? Enjoy a 10 minute walk down some of the most beautiful streets in Chicago. Ideal for families seeking comfort, style and a convenient location.

Guest favorite

The kitchen features modern appliances, including a stove and microwave, alongside a smooth countertop. A textured rug runs down the hallway, leading to a circular table situated in a well-lit space, characterized by warm brick accents on the walls.

Apartment in Lake View

4.93 out of 5 average rating, 204 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Welcome to our family-friendly & cozy 1-bedroom/1 bathroom apartment! We are walking distance from Wrigley Field, Montrose Beach, Andersonville restaurants, Green Mill Jazz Club, Riviera, Lincoln Square, Target and grocery. Close to Red, Purple & Brown CTA trains and 22, 78 bus lines to reach airports & top sights. Street parking is open & free (check signage!) We are a smoke-free home directly across from a school with playground in a very quiet & safe neighborhood: Ravenswood/Uptown.

Guest favorite

A narrow hallway leads to a kitchen area, featuring a white gas stove and a quaint wooden bench along one side. A bulletin board filled with notes and photos decorates the wall. Natural light streams through a nearby window, illuminating the space.

Apartment in Logan Square

4.95 out of 5 average rating, 692 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

A cozy living area features a comfortable sofa and two armchairs, with natural light entering through multiple windows. The space is decorated with framed artwork on the walls and a small side table. A television is positioned for easy viewing.

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

The exterior of the Coach House features white siding and a covered entry, framed by greenery. Two doors are visible, leading into the house, while a decorative wall piece is positioned above the entrance. A pathway lined with plants guides the way to the front steps.

Guesthouse in Batavia

4.91 out of 5 average rating, 293 reviews

Quaint Batavia Coach House

The Coach House is located behind our house. It is a private and separate little house. It is located close to the river path and lots of restaurants. The upstairs is one big room that has 1 queen and 2 twin beds. The upstairs also has a full bath. The TV in main living area on first floor is not hooked up to cable, but you can log into all of your apps and have access to news via YouTube TV, Netflix, Prime etc.

Guest favorite

A bright, open living area features a gray sectional sofa, a coffee table, and a light-colored rug. Large windows provide ample natural light, while a ceiling fan adds comfort. A dining area and kitchen are visible in the background, enhancing the spacious feel.

Townhouse in Edgewater

4.95 out of 5 average rating, 259 reviews

The Nancy’s gorgeous , Spacious Urban Getaway

This conveniently located and newly renovated townhouse in Edgewater features tons of sunlight and plenty of room for large families or groups. Near the lakefront, Loyola University, Andersonville, and tons of great restaurants and bars. In close proximity to the Red line "El" train, the city bus (22 Clark) and just four (4) miles from Evanston and Northwestern University.

Guest favorite

The exterior of a charming Victorian house is showcased, featuring a white facade, large windows, and a decorative entryway. An American flag hangs from the porch, surrounded by greenery and a well-maintained pathway leading to the entrance.

Apartment in Lake View

4.9 out of 5 average rating, 183 reviews

Clean, spacious, walk to Wrigley! Self check-in!

Park your car and forget it- or just leave it at home! Charming 3 BR first floor apartment in a Victorian building in the ultimate location, perfectly situated between Wrigleyville and Lincoln Park in the beautiful, vibrant Lakeview neighborhood. Guys seriously… this is the ideal neighborhood for a Chicago getaway or visit with family.

Top guest favorite

A cozy living area is shown, featuring two dark leather chairs and a matching ottoman. A built-in wooden shelving unit holds books and decorative items, while a flat-screen TV is mounted above a stone fireplace. Natural light filters through the window treatments.

Home in Lake View

4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.