Holiday houses in Northwest Side

4.96 out of 5 average rating, 116 reviews

Condo in Chicago

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 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. Free parking on Lawndale Ave.

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

4.97 out of 5 average rating, 162 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.

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!

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.

4.94 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

4.97 out of 5 average rating, 75 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

4.99 out of 5 average rating, 97 reviews

Plants and Art | Near Trendy Restaurants & Bars

Light-Filled Apartment Near Chicago’s Best Restaurants & Bars • Friends & Couples • A/C • Coffee Station w/Local Beans • Fully-Equipped Kitchen Whether you’re in town to explore or unwind, you’ll love the proximity to restaurants, cafes, and live music venues.The apartment is the perfect home base for your Chicago adventure. Fees: Early Check In@ 2pm : $50 Late Checkout@ 1pm: $50 Shipping: $25 + UPS fees Required for stays of 7+ Days: $100 Mid-Stay Cleaning

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.

4.87 out of 5 average rating, 39 reviews

Little cozy garden unit in quiet Neighborhood

Experience the ultimate retreat in this charming garden unit, perfectly situated in Chicago's vibrant Jefferson Park Neighborhood. 🏡🚿🧼🪴 Enjoy quality time with loved ones, including your furry friends, in this pet-friendly oasis 🐶🐕🐈🐾 With everything you need just steps away 🛍️🛒🚌🚞🏋️ Plus, take advantage of free parking on the spacious, all-way street 🚙 🅿️ We offer all necessary amenities for a home-like staying experience 🛀🛌📺

4.95 out of 5 average rating, 123 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!

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Popular amenities for Northwest Side holiday rentals

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Free parking on premises

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Other great holiday rentals in Northwest Side

5 out of 5 average rating, 15 reviews

Private room in Chicago

“The Incas Empire Suite” - Free Parking

Juan CarlosRating, 5 stars1 week ago

This place is so peaceful and beautiful. Roberto and Carlos are both really attentive and kind. This is my place to stay next time I visit Chicago.

4.95 out of 5 average rating, 19 reviews

Private room in Chicago

Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan

LiRating, 5 stars1 week ago

I really liked it here and would choose to stay again the next time I pass through Chicago.

4.96 out of 5 average rating, 190 reviews

Private room in Evanston

Welcoming Evanston Home

JoshuaRating, 5 stars2 weeks ago

Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

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 stars2 weeks 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!

Superhost

Private room in Skokie

4.79 out of 5 average rating, 109 reviews

Room w/ Amenities Mins to Downtown Chicago & NU!

RamRating, 5 stars2 weeks ago

Musa's place was extremely comfortable, very nice and easy to find! Check-in instructions were very clear, and the area itself is very peaceful. Surrounding streets are walkable as well, and it's a very short drive to a train station to quickly get downtown if needed.

Superhost

Private room in Chicago

4.88 out of 5 average rating, 17 reviews

Private Bedroom #3 w/ Shared Spaces

RichardRating, 5 stars1 week ago

Great host. Always responded fast and very respectful. The place was very clean and fellow travelers staying there were nice as well. Great location and peaceful neighborhood as too. Will book again in the future!!

Private room in North Riverside

4.93 out of 5 average rating, 215 reviews

The Albany Park Room at the Cape Cod in Riverside

GianfrancoRating, 5 stars1 week ago

I had an amazing experience staying at this Airbnb! From the moment I arrived, everything exceeded my expectations. The space was spotless, beautifully decorated, and exactly as described—if not better. The bed was incredibly comfortable, and all the little touches (like fresh towels and local recommendations) made it feel like a home away from home. The host was outstanding—friendly, responsive, and genuinely committed to making sure I had a great stay. Check-in and check-out were seamless, and they went above and beyond to accommodate any questions I had. The location was perfect: quiet and peaceful, but still close to restaurants, shops, and everything I wanted to explore. Whether you’re traveling for business or a getaway, I highly recommend this place. I’ll definitely be coming back!