Holiday 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

Apartment 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!

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.

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.

4.94 out of 5 average rating, 162 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.

4.95 out of 5 average rating, 122 reviews

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!

Superhost

Guest house in Chicago

4.91 out of 5 average rating, 100 reviews

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.

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Popular amenities for Northwest Side holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Northwest Side

Private room in Franklin Park

4.96 out of 5 average rating, 126 reviews

Safe & Clean King size Bed Next to Ohare/Rosemont

PhoebeRating, 5 stars1 week ago

Joswe was so incredibly kind and accommodating! Being a solo traveler it felt like a home away from home. The space was clean and comfortable and felt very safe. Joswe even left freshly brewed hot coffee every morning along with breakfast! I couldn't recommend Joswe or his home enough! if I could give more stars, I would!

4.91 out of 5 average rating, 104 reviews

Private room in Evanston

Room Mins to Downtown Chicago & Northwestern!

NataliaRating, 5 stars6 days ago

Musa was very friendly and helpful the entire time we stayed at his place. The house is big, neat and located in a nice and calm neighbourhood, ideal if you want to rest after a day in downtown. Good shops nearby so I recommend go for a walk around the beautiful Evanston.

Private room in North Riverside

4.93 out of 5 average rating, 214 reviews

The Albany Park Room at the Cape Cod in Riverside

MingleRating, 5 stars5 days ago

The place was a wonderful stay — both the bathroom and bedroom were exceptionally clean and well-maintained. However, if you’re planning to travel by car, I recommend reviewing the house rules carefully before booking. First, the driveway only accommodates one-way traffic for a single vehicle at a time. Second, street parking is prohibited between 2 AM and 6 AM. These two rules combined mean that guests must park in the driveway overnight. However, the host typically needs access to the driveway early in the morning. The host offers to move guests’ cars to the street in the morning. While this is a considerate idea, especially for those who don’t want to wake up early just to move their car, we felt a bit uneasy about it. Having previously experienced a street parking accident, we wanted to avoid any added mental stress associated with someone else moving the car for us. And it will be hard to argue with the insurance if the host was hit when trying to move our car.

4.83 out of 5 average rating, 210 reviews

Private room in Chicago

Lovely Bedroom 3 in a New Renovated Apartment

AlyssaRating, 5 stars2 weeks ago

Tippi was a great host! The room was clean & comfortable. The area has a few gems and great transport options. Would definitely recommend to others to stay if you're looking for a place not too far out of the city!

Superhost

Private room in Chicago

4.8 out of 5 average rating, 223 reviews

Skyline Room, near Medical Ctr, Upstairs

ThoRating, 5 stars5 months ago

Enjoyed my stay, very clean and comfortable. Very convenient and close to airport, train station, bus stop, etc. The host is amazing and responsive to guest’s needs.

5 out of 5 average rating, 3 reviews

The Logan Greystone

MariaRating, 5 stars1 week ago

Such a lovely and beautiful home! We were not aware the hosts live on the first floor so it felt a little less private (even though it is totally separate). However, we adored this place, it was furnished beautifully and felt super comfortable and clean. There were tons of appliances, spices, teas, cleaning supplies, everything! 10/10 would stay here again. Found parking right in the street too, super nice! Thank you :)

4.96 out of 5 average rating, 26 reviews

Private room in Chicago

Private Bedroom #1 w/ Shared Spaces

PaolaRating, 5 stars2 weeks ago

perfect place to stay for a quick trip! quang was very responsive and even assisted shipping back an item we forgot. the place quaint and perfect for 2. very pleased with our stay!