Kid-friendly holiday rentals in Downtown Chicago

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Downtown Chicago

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

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Guest favourite

Flat in Chicago

5 out of 5 average rating, 241 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Guest favourite

Guest suite in Chicago

4.96 out of 5 average rating, 331 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 favourite

Flat in Chicago

4.84 out of 5 average rating, 209 reviews

Cozy Northside Apt near Trans&Beach&Free St Prking

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.

Guest favourite

Flat in Chicago

4.99 out of 5 average rating, 218 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.

Superhost

Flat in Chicago

4.91 out of 5 average rating, 11 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: -Uber-fast Wifi streaming, -Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches for living - Designed for an aristocratic feel - The touristy 606 Trail access 100ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Guest favourite

Home in Elmhurst

4.96 out of 5 average rating, 105 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

Flat in Oak Park

4.75 out of 5 average rating, 144 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

Superhost

Apartment in Chicago

4.83 out of 5 average rating, 332 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!

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 361 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

Flat in Evanston

4.82 out of 5 average rating, 169 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/1.5ba 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!

Superhost

Flat in Berwyn

4.88 out of 5 average rating, 241 reviews

Bunks and 4 post bed apt.

The perfect jumping off point for exploring Chicago, we are located in hidden gem Berwyn, just 2 blocks from the train station. Child-friendly, free parking. Our home is also the site of a micro-flower farm, with pocket forest, native garden, fruit trees and kids play house. Our first floor apartment also has a crib, high chair, bunkbeds and free street parking.

Guest favourite

Flat in Chicago

4.9 out of 5 average rating, 173 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.