
Family-friendly vacation rentals in Northwest Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Northwest Side
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Chic & Cozy home @ Irving Train Stop
Relax in this chic and artfully designed condo. This sun-kissed 2-bedroom top-floor apartment in Irving Park is located in the city, but away from the hustle and bustle in a tree-lined quiet green neighborhood You can go just about anywhere in the city in 20 - 30 min as we are 2 minutes to the 24/7 EL blue line stop (train) and the I90/94 interstate. Our apartment is perfectly situated halfway between downtown Chicago & O’Hare airport. We are in a crime-free part of Chicago & have FREE PARKING

Peaceful Portage Park Apartment
You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

The Colorful Little Apartment
Cozy 1-bedroom basement apartment located in vibrant Logan Square where you’ll find great restaurants, bars, and cafés. There's a bus stop half a block away and a large grocery store one block away. Free street parking. The unit boasts many amenities to make your stay comfortable, including a full kitchen, a bedroom with a queen size bed, and a living room with a futon bed. The ceiling is low in some areas, making the unit better suited for people who are 5ft., 10in. (177.80 cm) or shorter.

Amazing 2 bedroom apartment on prime location
Spacious 2 bedroom garden apartment with plenty of light. Prime location, 10 min drive to O'Hare Airport, 15 min drive to Down Town Chicago. In town and want to see World Champions Chicago Cubs? Wrigley Field is only 6 miles away! Walking distance to Metra, Jefferson Park CTA Terminal, stores and restaurants. Parking available steps away from the front door. Rosemont Park Place and Convention Center 8 min Fashion Outlets of Chicago 10 min Wodfield Mall 20 min Old Orchard mall 15 min

Newly updated 1BD/1B in Old Irving Chicago!
Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

The Vanderpool House
The Vanderpool House has a Private Suite in a historic 100 year old Chicago Bungalow just 2 blocks away from the 2nd largest transit center in Chicago. The Blue Line L stop will take you downtown, the airport, or the Rosemont Convention Center. The Metra train will take you downtown or the northwest suburbs and you have 13 bus lines will take you anywhere else. Onsite parking is available at no extra charge. Theaters, Neighborhood Restaurants, Art Museums within walking distance.

Charming/Cozy Chicago Bungalow Garden unit 1BR/1BA
Private classic cozy Chicago bungalow garden unit | 1BR/1BA with private entrance. Located on Chicago’s NW side near Addison & Cicero between downtown and O’Hare. Fully furnished with a queen bed, living room, full kitchen, and Smart TV (use your own streaming logins, no cable). No shared spaces. Thermostat is upstairs but I’m happy to adjust for comfort. The owner lives upstairs and is available if you need anything during your stay. Relax, unwind, and enjoy your Chicago stay!

Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Belmont Pleasures - hot tub / arcade gaming room
Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Cozy Jefferson Park 2BR Apt
A lovely 2nd floor apartment flooded with natural light in a 2-unit building located in Jefferson Park. Conveniently located near O’hare airport, filled with small businesses, dive bars, and family-owned restaurants. Downtown Chicago will take 20-40 minutes, depending on traffic. My partner and I live in the unit below and can answer any questions you may have throughout your stay. We have created a warm and safe place for all to feel welcome!

Eddy Street Upstairs Apartment
Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!
Popular amenities for Northwest Side family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

Master qtr close to nature & easy urban facilities

Tea Studio in Wicker Park Spring Factory

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

33rd-Floor Penthouse with Breathtaking Views

The Spa of Downtown Whiting

Cozy Lakefront! Hot Tub-Fishing-Kayak &Pool Table

Private hot tub - King bed suite - Free parking
Family- and pet-friendly home rentals

Beverly Cottage Loft

Spacious 3BR • Great for Groups • Fast WiFi • Pets

ITALIAN garden apt/kids friendly/great location!!

Stylish 2BR stunner w/ unbeatable location

The Chicago River House – GIANT wall projector!

Cozy 2BD/1BA in Charming Logan Square

Newly-renovated historic home in Logan Square

The Sunshine Spot
Family-friendly home rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Level Junior Two Bedroom Suite | Fulton Market

Sentral Premium 2BR Apt South Loop Chicago

Spectacular 2BR Penthouse in the Loop | Roof Deck

Professional's Playground (Fitness Center • Sauna)

Whole Flat in Private Club. Walk to L, Dining & Shows

50th Floor Mag Mile Views, Balcony, Pool, Gym

Andersonville Luxury Pool Escape
Destinations to explore
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- Rentals with a washer and dryer Northwest Side
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- Family-friendly rentals Cook County
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- Family-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Wicker Park
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park




