House vacation rentals in Northwest Side

Find and book unique houses on Airbnb

Top-rated house rentals in Northwest Side

Guests agree: these houses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Chicago

4.96 out of 5 average rating, 316 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

Mar 17 – 24

R2,692 ZAR per night

Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 237 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Sep 7 – 14

R1,851 ZAR per night

Guest favorite

Home in Chicago

4.98 out of 5 average rating, 205 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!

Oct 29 – Nov 5

R3,044 ZAR per night

Guest favorite

Home in Chicago

4.96 out of 5 average rating, 126 reviews

Chicago Riverhouse summer on our 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. Amazing chef’s kitchen! 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Chill private patio with illuminating sofa

Jan 26 – Feb 2

R4,915 ZAR per night

Guest favorite

Home in Montgomery

4.84 out of 5 average rating, 108 reviews

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Aug 30 – Sep 6

R1,875 ZAR per night

Guest favorite

Home in Forest Park

4.91 out of 5 average rating, 223 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!

Jun 20 – 27

R2,659 ZAR per night

Guest favorite

Home in Chicago

4.94 out of 5 average rating, 209 reviews

Modern Home RoscoeVillage/Wrigley Free St Parking

The entire first-floor unit of this house is located in a safe, clean, and quiet area of Roscoe Village/Lake View, surrounded by shops and restaurants. It's just a 5-minute walk to the Brown-line Paulina station, 5 miles to downtown Chicago by L or car, 20 minutes walking to Wrigley Field, and 3 miles to Fullerton or Montrose Beach. It has an open-concept gourmet kitchen, full laundry, fast-speed WIFI, and Roku Streaming; complimentary Starbucks coffee beans for freshly brewed coffee.

Feb 7 – 14

R2,307 ZAR per night

Superhost

Home in Des Plaines

4.78 out of 5 average rating, 305 reviews

Urban Farmhouse near O'Hare

I am hosting a hundred year old farmhouse that has been completely renovated on the inside and outside. The beds are top quality and bought new. The neighborhood has unique places to dine and explore. It is close to Metra Rail Road to downtown Chicago. O'Hare International Airport is 7 miles from the house and Rosemont Convention Center is just 5 miles, both are accesable by car or public transportation. There is also a lot of parking. A great place to stay when you travel.

Sep 16 – 23

R2,405 ZAR per night

Guest favorite

Home in Chicago

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

This is a private three bedroom house you will be reserving in the Avondale neighborhood with plenty of available free street parking. The residence sits on the intersection of Elston, Rockwell and Wellington. We are in the middle of it all. You can shoot into downtown quickly or be in Wrigleyville within minutes to watch the Cubs. You’ll love this place because of the neighborhood and privacy. The space has been crafted by a well experienced host. 15 minute drive to downtown.

Feb 26 – Mar 5

R1,848 ZAR per night

Guest favorite

Home in Chicago

4.97 out of 5 average rating, 318 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Dec 5 – 10

R3,483 ZAR per night

Guest favorite

Home in Chicago

4.96 out of 5 average rating, 200 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

May 20 – 25

R5,327 ZAR per night

Guest favorite

Home in Chicago

4.98 out of 5 average rating, 175 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.

Jul 9 – 16

R4,302 ZAR per night