Kid-friendly vacation rentals in North Side

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in North Side

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

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Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 296 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

Oct 18 – 25

G$29,270 GYD per night

Guest favorite

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

Jul 28 – Aug 4

G$23,148 GYD per night

Guest favorite

Apartment in Avondale

4.97 out of 5 average rating, 118 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Jul 8 – 15

G$25,105 GYD per night

Guest favorite

Guest suite in Logan Square

4.97 out of 5 average rating, 226 reviews

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

Oct 1 – 8

G$23,440 GYD per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

Jan 10 – 17

G$23,421 GYD per night

Guest favorite

Guest suite in Irving Park

4.99 out of 5 average rating, 137 reviews

BnB on Grace Street - Modern 2-Bedroom Guest Suite

Welcome to Bnb on Grace Street in the charming Old Irving Park neighborhood, in one of the original homes built in 1893! Our private guest suite is modern and recently renovated while highlighting original features of the home such as the exposed brick walls. It's just 2 blocks from a major highway and from the El Train blue line, from which you can travel into downtown or out to O'Hare Airport. The suite includes 2 bedrooms, 1 bathroom, a kitchenette/dining area, and living room.

Oct 15 – 22

G$25,657 GYD per night

Guest favorite

Apartment in Uptown

4.96 out of 5 average rating, 267 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Oct 22 – 29

G$23,640 GYD per night

Superhost

Apartment in East Rogers Park

4.89 out of 5 average rating, 105 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

This gem is steps from Hartigan Beach, an eclectic mix of eateries, small theater venues, public transportation and Fine Wines & Spirits. You'll love my place because of the coziness and proximity to a swimming beach, on a friendly tree lined street. Conveniently situated between Loyola and Northwestern Universities. Rent a Divvy bike, call UBER/LYFT, rent a car and explore all that Evanston, Edgewater and Andersonville has to offer!

Oct 19 – 26

G$24,441 GYD per night

Guest favorite

Apartment in Lincoln Square

4.96 out of 5 average rating, 323 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.

Dec 10 – 17

G$27,333 GYD per night

Guest favorite

Guest suite in Lincoln Square

4.94 out of 5 average rating, 178 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

Sep 16 – 23

G$20,835 GYD per night

Guest favorite

Condo in Lincoln Square

4.97 out of 5 average rating, 330 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Sep 24 – Oct 1

G$30,782 GYD per night

Guest favorite

Apartment in Portage Park

4.99 out of 5 average rating, 181 reviews

NW Chicago Apartment in Safe Neighborhood

We have a lower level apartment available located on the northwest side of Chicago. Our neighborhood is mostly Chicago style brick bungalows with plenty of free street parking available. We have easy access to public transportation, including a night owl bus (runs 24 hours) only 3 blocks away. We welcome guests from every culture and background.

Aug 13 – 20

G$24,037 GYD per night