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Family-friendly vacation rentals in Near North Side, Chicago

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Near North Side, Chicago

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

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Rental unit in Lincoln Park

4.79 out of 5 average rating, 159 reviews

Chicago Lincoln Park Getaway

Getaway to this sunny 2 bedroom, 1 marble bath home in the desirable East Lincoln Park neighborhood. Our dream location is THE place to be - next to restaurants, nightlife, transportation, and entertainment. Walk to the Lakefront (0.7 miles), the North Pond Nature trails (0.1), the Lincoln Park Zoo (0.5 miles), and more! The 25M Morningstar mansion is across the street & the historic Wrigley Mansion a block away. For those traveling with youngsters, baby essentials are provided in the apartment.

Guest suite in West Town

4.96 out of 5 average rating, 331 reviews

Secret Garden | Noble Square | 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.

Rental unit in Roscoe Village

4.9 out of 5 average rating, 400 reviews

Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village

We converted our garden unit into a great space for travelers, we updated everything with you in mind, features high end appliances, full kitchen, 1 king and 1 queen pullout, heated floors, and free wifi. There are only 2 beds. We also have a landscaped backyard and grill access if requested If you need anything please let me know ahead of time Roscoe Village is often thought of as a small town inside the big city. It is one mile west of Wrigley Field and two miles west of the lakefront.

Rental unit in Lake View

4.96 out of 5 average rating, 279 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

Rental unit in Lincoln Park

4.96 out of 5 average rating, 408 reviews

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Rental unit in Roscoe Village

4.96 out of 5 average rating, 278 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Rental unit in Logan Square

4.84 out of 5 average rating, 785 reviews

Hip Chicago Apartment - FREE Parking Spot Included

You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

Rental unit in Logan Square

4.85 out of 5 average rating, 221 reviews

Bucktown Retreat - Why The Buck Not? Sleeps 1-6

Located in historic Bucktown, this 2 bedroom first floor condo has all the comforts and charm you'd expect and more. Need to work? Play? Relax? Easy access to/from the Loop/O'Hare? Our location has the best of what you are looking for. Located within a quiet street of Bucktown, you can hop skip and jump out the door to an ecclectic variety of local eateries, coffee shops, bars, shops, arts, amusement, and outdoor life. Let our place be your Bucktown Retreat - Why the Buck Not?

Rental unit in Magnificent Mile

4.94 out of 5 average rating, 235 reviews

Urban Chic Apartment by the Magnificent Mile

Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely, if ever, in the bedrooms.

Condo in Lincoln Park

4.84 out of 5 average rating, 341 reviews

Chic and Charming Vintage Condominium in Lincoln Park

View the city skyline from the windows and balcony of this lovely bright property in the heart of Chicago's safe and historic Lincoln Park neighborhood. With old-style elegance, wood floors, and an open fireplace, simple color schemes are delightfully offset by eclectic and inviting art. Let us introduce you to everything Chicago has to offer from the comfort of your own private getaway!

Condo in West Town

4.97 out of 5 average rating, 760 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

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

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Rental unit in The Loop

4.96 out of 5 average rating, 27 reviews

The Playwright's Palace

Home in West Town

4.85 out of 5 average rating, 307 reviews

Lux Urban 3BR/3BA Duplex + Parking!

Loft in West Town

4.81 out of 5 average rating, 283 reviews

Artist Loft Duplex in a 1904 Former Factory

Rental unit in The Loop

4.75 out of 5 average rating, 44 reviews

The Professional's Playground

Home in Logan Square

4.9 out of 5 average rating, 87 reviews

LOFT606: Gigantic Sunlit Former Factory Home

Condo in Logan Square

4.98 out of 5 average rating, 258 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Rental unit in Bronzeville

4.46 out of 5 average rating, 13 reviews

Spacious 2bdm unit 15min to Dwtn

Rental unit in Near South Side

4.87 out of 5 average rating, 196 reviews

Skyline Serenity: Sauna, Hot Tub, Peloton, Views

Family- and pet-friendly home rentals

Condo in West Town

4.89 out of 5 average rating, 257 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Home in Lincoln Park

4.84 out of 5 average rating, 158 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Rental unit in Logan Square

4.9 out of 5 average rating, 379 reviews

Sunny Logan Square Artists' home

Guest suite in Portage Park

4.95 out of 5 average rating, 149 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Rental unit in Logan Square

4.87 out of 5 average rating, 301 reviews

Logan Square Video Game Loft

Rental unit in Wrigleyville

4.75 out of 5 average rating, 213 reviews

Cozy Bedroom in Wrigleyville (Entire Apt)

Rental unit in Logan Square

4.96 out of 5 average rating, 102 reviews

Garden Unit Getaway-Bucktown

Home in Lincoln Park

4.82 out of 5 average rating, 222 reviews

Spacious Luxury Townhouse - Old Town

Family-friendly home rentals with a pool

Rental unit in The Loop

4.63 out of 5 average rating, 56 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

Rental unit in The Loop

4.77 out of 5 average rating, 204 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

Guest suite in Bridgeport

4.96 out of 5 average rating, 82 reviews

Sweet Home Chicago-9min downtown/pool/free parking

Guest suite in Berwyn

4.67 out of 5 average rating, 42 reviews

Music Hot Spot’s Main Level

Rental unit in The Loop

4.77 out of 5 average rating, 227 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

Quick stats about vacation rentals that are family-friendly in Near North Side, Chicago

Total rentals
540 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
23K reviews
Pet-friendly rentals
220 properties allow pets
Rentals with a pool
200 properties have a pool
Rentals with dedicated workspaces
400 properties have a dedicated workspace

Destinations to explore