Holiday rentals in Northwest Side

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Top-rated holiday rentals in Northwest Side

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Guest favourite
A studio space is presented with a spacious bed in the background, complemented by a wicker swing chair nearby. A vintage SMEG refrigerator and a dining table with stools enhance the ambiance, while a textured area rug lies on the hardwood floor beneath.
Flat in Chicago
4.92 out of 5 average rating, 724 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

A vintage lovers dream! This loft was designed with a love for the past. Starting in the kitchen, you’ll see the beautiful zinc alloy countertops are complemented by gorgeous antique mirror backsplashes. You’ll have access to a stovetop, microwave, coffeemaker, as well as basic tools and kitchen supplies. There is a lovely throwback SMEG 50’s refrigerator and the shelves are all reclaimed wood. This antique lumber detail can be found throughout the loft, from the floors all the way to the night stands. The bathroom door may be recycled wood and the mirrors antique, but the shower fixtures are all Grohe. There is also a hair-dryer as well as complimentary toiletries and clean towels for your use. At the end of the day, you can sit on our funky wicker swing chair and think of all the chic guests who may have used the closet doors that were brought in from NY’s Plaza hotel! You’ll surely have the sweetest of dreams when you go to sleep on the memory foam mattress following a quick binge using the complimentary netflix. Additional amenities include self-controlled A/C and closet space with hangers, an iron and ironing board. This loft is very well kept, professionally cleaned and sanitized after each and every use. When booking this studio you will have full and private access to the entire apartment. There is a shared deck and lounge area you are welcome to use. For your convenience, we have arranged luggage drop-off/storage before and after your stay at the restaurant right down stairs - do note this is a courtesy. Our check-in and check-out process is automatic and seamless, once you book you will receive a private entry code ahead of your stay. Check-in any time after three pm as late as you'd like, check-out on or before 11 am. Due to our cleaning schedule we cannot accommodate early check-ins or late check-outs. The provided free parking spot is located a block away from the Airbnb unit Someone who’s offsite will be available as needed Set between South Old Irving and Kilbourn parks, the studio is located in one of Chicago's most historical neighborhoods. Sample the craft beer taverns and cocktail bars lining North Milwaukee Avenue. Wrigley Field is about 10 minutes away by car. The quickest and most inexpensive way to get around is via Uber or Lyft. If reaching the apartment by vehicle, there is free street parking in the surrounding neighborhood (please follow the local laws and signs). Public Transportation guide to the apartment: From Chicago O'Hare Int'l Airport: Take the Blue Train line to Irving Park Station and then transfer to the CTA #53 Milwaukee bus line to reach the apartment. You can also take the Blue Train line to Jefferson Park Station and then transfer to the CTA #56 Milwaukee bus line to reach the apartment. To/From Downtown Chicago: The CTA #56 Milwaukee bus is a very convenient and direct way to reach the Downtown Chicago Loop with a station just below the apartment. To/From Wrigley Field: Easily catch a game via the 77 or 152 buses, with a station just close by the apartment. Train and bus maps can be found and downloaded here: https://www.transitchicago.com/maps/ Please note that the provided free parking spot is located a block away from the Airbnb unit.

Top guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Flat in Chicago
5 out of 5 average rating, 65 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Top guest favourite
A spacious bed is adorned with layered bedding, featuring a variety of pillows in soothing hues. Soft light from a nearby window creates a serene atmosphere, and a decorative stained glass piece adds a touch of artistry to the room.
Guest suite in Chicago
4.97 out of 5 average rating, 315 reviews

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

Guest favourite
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.
Flat in Chicago
4.86 out of 5 average rating, 244 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.

Top guest favourite
A charming garden unit is situated within a light-colored, two-story building, framed by a white picket fence. The entrance is marked by a set of steps leading to a spacious porch, where seating may be present. Nearby trees and greenery accentuate the inviting exterior.
Flat in Chicago
4.92 out of 5 average rating, 76 reviews

Montrose Gardens

Nestled in the heart of one of Chicago’s most diverse neighborhoods, our garden unit offers a space to stay back and relax, while maintaining a short commute to all areas of the city. Minutes from the blue line, 20minutes from the lake, downtown, the united center, wrigley; we find ourselves in a truly great location. On-site parking, pet friendly, and a private outdoor area for the airbnb. Hosts are right above if you have any questions or need a recommendation!

Top guest favourite
A spacious living area features a dark leather sofa and a modern accent chair beside a circular glass coffee table. A patterned area rug in neutral tones lies on the hardwood floor, while a dining area with a round table and chairs is visible in the background.
Home in Chicago
4.97 out of 5 average rating, 220 reviews

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.

Guest favourite
A well-lit bedroom features a spacious bed with soft linens, complemented by stylish nightstands on each side. A 55" smart TV is mounted on the wall, while decorative elements like a flower and soft towels enhance the serene ambiance. Skylights and large windows provide ample natural light.
Apartment in Chicago
4.91 out of 5 average rating, 22 reviews

Chic Chicago Spa Retreat – Luxe & Light-Filled

Experience top-floor luxury in this fully remodeled Avondale condo. Soak in the spa-style bath, bask in natural light from skylights, and relax with cozy furnishings, a king-size bed, and oversized smart TVs. Cook with ease in the sleek, fully stocked kitchen, or explore nearby Logan Square gems and Milwaukee Ave’s dining scene. Garage parking is included, and the Blue Line offers a direct ride to downtown or O’Hare—city access, minus the hassle.

Top guest favourite
Private room in Chicago
4.84 out of 5 average rating, 225 reviews

Lovely Bedroom 3 in a New Renovated Apartment

This is one of two rooms in my apartment that listed on AirBnB. There is one bathroom to be shared with other guests. My home is midway between O'Hare Airport and Downtown Chicago in a safe and quiet neighborhood. It's very convenient whether you drive or use public transportation (20 minutes to O'Hare, 25 to the Loop on Blue Line, CTA and Metra train stations are 3 blocks away). This is on the second floor and there is no elevator.

Guest favourite
Private room in Chicago
4.82 out of 5 average rating, 374 reviews

Loft Style Private Apt 2 (1 Room- 420 Friendly)

Please do not book unless you read the entire listing, including all house rules & amenities. No refunds will be given if you book without first reading the house rules Near Loyola University. 420 friendly environment. No Cleaning Fee, Full Kitchen, Living Room, 1 Shared Bathroom, Internet, Heat, Air Conditioning Redline, CTA, Beach, Groceries, Gyms, Multiple Bars & Diverse Cuisine within 5-15 min walking

Top guest favourite
A well-equipped kitchen is visible, featuring modern appliances and cabinetry. A comfortable seating area includes a dark sofa with accent pillows and a matching ottoman. Soft lighting creates a calming ambience, complemented by a decorative wall art piece above the couch.
Flat in Chicago
5 out of 5 average rating, 28 reviews

Chicago Addison St. 1 bed/1 bath condo, Garden Lvl

You'll have a great time at this comfortable place, 12 minutes from o’Hare airport and 20 minutes from downtown, dunning pour house is a nice bar&restaurant just 2 buildings down from the place, which is nice you don’t have to drive or look for parking, there is a park across the street also walking distance and couple of grocery and liquor stores plus a dry cleaner also walking distance!

Guest favourite
A cozy bedroom features a spacious bed dressed in a light blue and gray striped blanket. A decorative pillow adds a touch of color. Natural light enters through a window beside the bed, and a simple mirror reflects the neutral tones of the room.
Flat in Chicago
4.95 out of 5 average rating, 110 reviews

Modern 1-Bedroom w/ off-street parking space

Kick back and relax in this calm, newly renovated apartment with quartz countertops, natural light, and in-unit laundry. 0.7 miles from both the Belmont Blue line and the Logan Square Blue line north entrance (outside The Dill Pickle). Walk to shops, bars, and restaurants on Milwaukee Ave. High speed 1000 Mbps internet. Free parking in the dedicated off-street parking space.

Top guest favourite
A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.
Guest suite in Chicago
4.96 out of 5 average rating, 139 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!

Popular amenities for Northwest Side holiday rentals

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