Kid-friendly vacation rentals in Northwest Side

4.96 out of 5 average rating, 28 reviews

An open sleeping area features a spacious bed with a grey upholstered headboard, accented by plush pillows. A decorative throw sits on the bed. The sloped ceiling creates a unique architectural detail, while a window provides natural light. A small bedside table and a wicker basket add functionality.

Place to stay in Chicago

Cute Chicago Attic Loft! Walk to CTA, Easy Travel

Welcome to our newly renovated attic in-law suite in our vintage, 120 year old Chicago home! This bright, airy loft boasts a brand new full bathroom with a large, beautiful walk in shower. The unit has a newly built kitchenette with vintage hardware, a new fridge and freezer, and microwave. Conveniently located between O'Hare and Downtown Chicago, this space is situated perfectly for your Chicago visit! We’re a 2min drive from I-90 & I-94, a 5min walk to the train, and a 2min walk to the bus.

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

4.94 out of 5 average rating, 421 reviews

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

A bright and airy attic space is characterized by soaring white shiplap walls and rustic wood flooring. A comfortable sectional sofa and lounge chair are positioned around a glass coffee table. Natural light floods in through multiple skylights, illuminating the cozy bedroom area visible in the background.

4.97 out of 5 average rating, 160 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.

A living area features a dark leather sofa with red accent pillows, paired with two leather chairs. A wooden coffee table sits centrally, surrounded by warm-toned lighting. The space opens to a kitchenette with a retro red refrigerator and tall bar seating, creating an inviting atmosphere.

4.86 out of 5 average rating, 223 reviews

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

A cozy sitting area features a vibrant orange sofa adorned with black cushions and a matching ottoman. A wooden desk with a red chair sits nearby, while a floor lamp casts a warm glow. Bright artwork depicting flowers adds a touch of color to the wall.

4.97 out of 5 average rating, 293 reviews

Stylish Studio in Historic Logan Square

Modern garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom and kitchenette is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a magical shared backyard space. The owner's treehouse deck can be reserved. An oasis in the city with exciting city easily accessible!

4.87 out of 5 average rating, 127 reviews

A modern living area features a blue sectional sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front of the sofa. A desk and chair are situated near a large window, allowing natural light to brighten the room.

Condo in Chicago

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.

A cozy bedroom features a spacious bed dressed in coral bedding. A nightstand with a decorative tray sits next to the bed, while a small bookshelf displays various items. A window provides natural light, and artwork adorns the walls, contributing to a welcoming ambiance.

4.94 out of 5 average rating, 18 reviews

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.

A game room features vibrant red walls adorned with colorful murals and various arcade cabinets. A pool table occupies one corner, while a foosball table is positioned nearby. Bright overhead lighting illuminates the space, enhancing the lively atmosphere for entertainment.

4.98 out of 5 average rating, 118 reviews

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.

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

4.94 out of 5 average rating, 163 reviews

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

A spacious living area features a gray sectional couch adorned with colorful city skyline art above. Natural light floods in from large windows, complemented by a standing lamp. A dining area with a glass table is visible in the background, enhancing the airy atmosphere.

4.97 out of 5 average rating, 74 reviews

Bright, Modern 2 BR in Logan Square w/ Parking

Come and enjoy everything the trendy Logan Square neighborhood has to offer while staying in a quiet, cozy 2nd floor apartment with a parking spot! In a quiet residential neighborhood. Steps away from hip coffee spots, a host of restaurants steps away, supermarkets and more. As well as a park at the end of the block with a playground and cross training area. 20 minute drive to Downtown and O'hare Airport with access to public buses, trains, and Divy Rental bikes

The cozy suite features a spacious bed with soft bedding, accompanied by a reading chair and ottoman. A small bookshelf holds various books, and two windows allow natural light to fill the room. A potted plant adds a touch of greenery to the decor.

4.96 out of 5 average rating, 26 reviews

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.