Vacation rentals in Northwest Side

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Top-rated vacation rentals in Northwest Side

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Guest favorite

The kitchenette features a compact black refrigerator and a microwave situated beneath a sloped ceiling. Shelves with dishware and utensils are installed above a wooden countertop, which complements the white cabinetry. A modern sink with a gold faucet adds an elegant touch to the space.

Place to stay in Chicago

4.97 out of 5 average rating, 29 reviews

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.

Guest favorite

A staircase leads down to a private entrance of the garden unit, featuring a concrete pathway. To the side, a fenced area contains a Siberian husky. The entrance is well-lit, illuminating the steps and pathway, providing a welcoming access point.

Apartment in Chicago

4.86 out of 5 average rating, 133 reviews

Classic Chicago Bungalow Garden Unit 1bdrm 1 bath

Classic Chicago Bungalow garden unit apartment furnished with a queen bed, living room, and everything you & your guests need to enjoy your stay in Chicago! Make yourself at home once you arrive. Traditional cable TV is not included in your stay, we do provide a smart tv, Feel free to use with YOUR own login and enjoy! Located in Chicago northwest side. Use Addison and Cicero as your cross street to determine gps and location. Your space is separate with no shared common areas. Owner lives above

Top guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 172 reviews

Roomy Retreat | Easy Parking | Walk to Train

Light-Filled Apartment | 20 Min Downtown | O’Hare ✔ Free Street Parking ✔ Fully-Equipped Kitchen ✔ Friends/Couples/Families ✔ Walk to Cafés & Restaurants ✔ No Stairs Perfect for friends and families, our home offers easy access to sightseeing while embracing the charm of a vibrant, walkable neighborhood. Extra Fees: *only available upon request and approval* Early Check In@ 2pm : $50 @10am:$100 Late Checkout@ 1pm: $50 @9pm:$100 Shipping: $25 + UPS fees Required for 7+ Days: $80 Cleaning

Guest favorite

A modern bathroom showcases a mid-century modern vanity in natural wood with two drawers. Above it, a round mirror is complemented by a pendant light. A white toilet is positioned nearby. White hexagon tiles cover the floor, while a skylight fills the room with natural light.

Apartment in Chicago

4.97 out of 5 average rating, 163 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.

Guest favorite

The kitchen area features modern stainless steel appliances, including a gas stove and large refrigerator. Granite countertops provide ample workspace, with stylish cabinetry along the walls. A kitchen island offers additional seating, complemented by two black stools. Natural light filters through the nearby sliding door.

Townhouse in Chicago

4.97 out of 5 average rating, 92 reviews

Cozy & Bright Townhome near O’hare -Self Check In-

Escape into this Montclare Masterpiece! Be one of the first guests to enjoy our revitalized, fully-stocked home with attached deck. This 3-level home comes with a spacious, light-flooded living area with attached open kitchen w/ SS appliances, granite countertops/ backsplash, and accent lighting - perfect for larger groups. On the third level you'll find 2 elegant bedrooms with ample closet space, updated full bathroom, and in unit washer and dryer provide all the essentials and more!

Guest favorite

The exterior of a historic brick building is prominently displayed, featuring a detailed entryway with wooden doors and multiple large windows. Decorative elements are noted in the architecture, complemented by a small green bush alongside the steps leading to the entrance.

Apartment in Chicago

4.94 out of 5 average rating, 78 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!

Guest favorite

A world map is prominently displayed on a light green wall, providing a colorful and educational focal point. A wooden coat rack is positioned to the side, while a metal drying rack with several clips stands against the wall.

Apartment in Chicago

5 out of 5 average rating, 6 reviews

LairBnB - Garden Apartment

Welcome to LairBnB! This is a private garden apartment with separate egress in our home near 6 corners in Portage Park. The ceiling height is 76”. Guests under 6' tall will be most comfortable here. We are old school Airbnb SuperHosts who love to host adult travelers in town for work or events in Chicago. We are steps away from Milwaukee, Cicero, and Irving Park bus stops, an 8 minute walk to the Grayland Metra stop, and a 20 minute walk to the Irving Park Blue line CTA.

A spacious living area features large windows allowing natural light to fill the room. A white sectional sofa is adorned with textured pillows and a throw. A circular table with two upholstered chairs complements a soft area rug, while indoor plants add a touch of greenery.

Apartment in Chicago

5 out of 5 average rating, 4 reviews

Modern Design 3 Bedroom Dandelion Apartment

Discover your stylish retreat in Avondale! This beautifully appointed 3-bedroom apartment seamlessly blends modern luxury with sustainable living. Sun-drenched, open-concept living space, leading to a chef's dream kitchen. Featuring sleek stainless steel appliances, custom cabinetry, and ample counter space, it's perfect for culinary adventures. This eco-conscious building boasts insulated walls, green construction, and solar panels providing complimentary electricity.

Top guest favorite

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Chicago

4.98 out of 5 average rating, 120 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.

Guest favorite

A well-organized kitchen features white cabinetry with glassware and dishes neatly arranged. Countertop appliances include a coffee maker, microwave, and toaster. A double sink is integrated into the space, with a window above providing natural light and a view of a small potted plant.

Home in Chicago

4.98 out of 5 average rating, 203 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 favorite

A charming brick exterior is presented, featuring a welcoming front porch with seating. Lush green landscaping surrounds the entryway, with well-maintained grass and shrubs adding to the outdoor appeal. The roofline is accented with a gabled feature, enhancing the overall character of the home.

Guest suite in Chicago

4.95 out of 5 average rating, 126 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!

Guest favorite

A modern kitchen is presented with a central island featuring three stools. White cabinets and black appliances are complemented by a geometric backsplash. A vase of flowers adds color to the countertop, while a waste bin and rug are positioned nearby, enhancing functionality.

Apartment in Chicago

4.88 out of 5 average rating, 16 reviews

Cozy Casa by O’Hare Airport

Welcome to Cozy Casa! Enjoy this stylish yet simple and cozy apartment located in a quiet neighborhood with contactless entry. There is one bedroom with a Queen-size bed. We offer free WiFi, free parking, a private enclosed back porch, free laundry as well as a fenced in back yard for your Furry friend! 10 minutes from O’hare airport and only 25 min from downtown!