Vacation rentals in Northwest Side

4.96 out of 5 average rating, 27 reviews

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.

4.94 out of 5 average rating, 420 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

4.87 out of 5 average rating, 127 reviews

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.

4.93 out of 5 average rating, 74 reviews

Top Floor Portage Park Lookout

Welcome to our bright, and spacious top floor apartment in Chicago. Enjoy the park vibes while being centrally located to all that the city offers. Just minutes away from O'hare airport and public transportation, enjoy exploring Chicago's downtown and the hip shops, dining, and culture in surrounding neighborhoods like Avondale and Logan Square. Stylishly decorated, our open-concept space offers a large bedroom and a fully equipped kitchen. Book now for a perfect Chicago experience!

Top guest favourite

4.98 out of 5 average rating, 61 reviews

Pine Beam Sloth Apartment next to Blue Line

Welcome to our charming 650 sq ft, 1-bedroom apartment It's the perfect size for comfortable living, offering a well-equipped full kitchen. The warm wood ceiling creates a cozy ambiance, while the functional layout maximizes space for relaxation. This apartment is ideal for solo travelers, couples, or even small families seeking a comfortable and convenient home base to explore Chicago. Located between O'hare airport and Chicago downtown next to Blue line Metro station.

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.

Top guest favourite

4.98 out of 5 average rating, 117 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.

Top guest favourite

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

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.

4.98 out of 5 average rating, 202 reviews

Home in Chicago

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.