Kid-friendly holiday rentals in Northwest Side

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

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.

Charming Garden Unit Portage Park

Cozy garden level guest suite with separate entrance in Portage Park! Enjoy a comfortable and private retreat (ceiling height varies 5'9"-6'9"), complete with a separate entrance for your convenience. You'll have exclusive access to a fully equipped basement, which includes a private bedroom, gym, laundry room, bathroom, Wi-Fi, living area and small kitchenette. In addition to your private space, you'll have access to shared outdoor areas, including a BBQ and fire pit.

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

Lovely Garden Studio Apartment.

Cozy garden suite apartment in a quiet part of town. This space is located in the lower level of a Bungalow house. There are 2 other units in the building, inhabited by a nice little family and a nice person. Close to Avondale and Logan Square nightlife, and a direct bus to Blue Line Trains is within walking distance. Great backyard, full of native plants and butterflies if you're craving some outdoors. Free parking on a side street a little down the block.

The Evergreen House

Relax and feel at home on the first floor apartment (completely private) of my Chicago 2-Flat. This home away from home is well stocked with anything that you might need whether you are staying for 2 nights or 2 months. There are 3 televisions with Wifi and Netflix throughout the apartment. There is a nice backyard that you are welcome to use and street parking is free. Washer and Dryer available in the basement. The highways and bus are also nearby.

Chicago getaway for two!

This cozy 1 bedroom 1 bath apartment on the second floor of a lovely home in Jefferson Park is the perfect place to stay in Chicago. Conveniently located near the blue line (Jefferson Park stop) and has a bus stop for 88W right in-front! This cozy 1 bedroom 1 bath apartment on the second floor of a lovely home in Jefferson Park is the perfect place to stay in Chicago.

Simple Unit Kids friendly

Welcome to our charming English Tudor-style home 🏡 in Chicago’s Dunning/Portage Park neighborhood. Enjoy a private, spacious, and quiet second-floor unit—perfect for families, couples, or business travelers. Features include natural light ☀️, free street parking🚙, and a relaxing atmosphere. Conveniently located between O’Hare Airport✈ and downtown Chicago.

NW Chicago Garden Apartment

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.