House holiday rentals in Northwest Side

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Top-rated house rentals in Northwest Side

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Guest favourite

Home in Chicago

4.95 out of 5 average rating, 367 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

Guest favourite

Home in Oak Park

4.97 out of 5 average rating, 107 reviews

Meticulous 1st Flr 3 bed, Kitchen & Free Parking

Enjoy our historic district two-flat w/ free parking in upscale, safe, walkable Oak Park just 3 blocks to the train for easy access to Chicago. Enjoy some tranquil time in our little urban farm. Check out the gardens and visit our 4 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties allowed. Minimum age to book, 25. Visit my profile for additional units.

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 151 reviews

Chicago River House with private patio!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and illuminating seats

Guest favourite

Home in Berwyn

4.99 out of 5 average rating, 109 reviews

Retro Modern Bungalow— fire pit + free parking

Experience the city in style at Retro Modern Bungalow. The perfect crash pad for up to four friends and two pups. Featuring two spacious bedrooms, each w/ a king bed + luxury linens, a propane fire pit and a fully fenced backyard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favourite

Home in Chicago

4.98 out of 5 average rating, 233 reviews

Wrigleyville Southport Studio

This Wrigleyville studio is the best of urban living combined with a tranquil retreat. With vintage, mahogany paneled walls and a comfy king size bed this apartment has everything! Free coffee, tea, snacks and dedicated work space. The Southport Corridor is blocks away with restaurants, bars and shopping. Free street parking and 4 blocks to El/ Brown/Purple/ Red line trains. Wrigley Field, Metro and Vic is 4 blocks away. This garden studio is the perfect retreat in the heart of Chicago!

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 113 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

Welcome to BoHo House - an airy bohemian gem from 1903. This 3 BR home is just minutes walking distance from popular Chicago bars, restaurants, and coffee shops. Let your pup roam in the private fenced-in backyard that features the most adorable outdoor space. This spot is just so peaceful. Host a nice patio dinner and get cozy by the fire, or hangout inside and put a movie on. 15 min from ORD, 10 min to downtown, 800+ Mbps WiFi speeds, free coffee, snacks, and secure 2 car garage parking!

Guest favourite

Home in Forest Park

4.91 out of 5 average rating, 256 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Guest favourite

Home in Chicago

4.98 out of 5 average rating, 187 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

Home in Chicago

4.97 out of 5 average rating, 109 reviews

The Hamlin In Logan Square 4BR/2BA w/Parking!

Welcome to The Hamlin House in Logan Square! Enjoy four bedrooms, two full bathrooms and complimentary two-car garage parking during your stay. This home is perfect for both family and group vacations in Chicago. Logan Square is a thriving neighborhood filled with amazing art, restaurants and architecture. The neighborhood provides easy access to downtown while avoiding downtown hotel pricing for larger groups.

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 107 reviews

3BD Home Mins from Airport | Free Wi-Fi + Parking

Cozy home near O'Hare airport with a huge park just behind the backyard, located in one of the safest neighborhoods in the City of Chicago. Quick access to the expressway and short walk to the CTA Blue Line train/bus station. Conveniently located within 5 miles of: - O'Hare Airport - Rosemont/Donald E. Stephens Convention Center - All-State Arena - Fashion Outlets of Chicago

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 105 reviews

Cozy/Spacious WFH Family Friendly w Permit Parking

Bright first-floor private apartment with free parking passes for permit-only street parking. Enjoy the wide-open windows, a private outdoor space, and two bathtubs for ultimate relaxation. Cook for yourself in the fully-equipped kitchen or explore some of the amazing restaurants nearby. Family/baby friendly with included highchair, pack n' play, crib, baby monitor, and more!

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 107 reviews

Chicago getaway for two!

This cozy 1 bedroom 1 bath apartment on the second floor of a lovely home in Jefferson Park is the perfect place to stay in Chicago. Conveniently located near the blue line (Jefferson Park stop) and has a bus stop for 88W right in-front! This cozy 1 bedroom 1 bath apartment on the second floor of a lovely home in Jefferson Park is the perfect place to stay in Chicago.