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House vacation rentals in Chicago

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Top-rated house rentals in Chicago

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

Guest favorite
Home in Chicago
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
$93 per night
Guest favorite
Home in Berwyn
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.
$80 per night
Guest favorite
Home in Chicago
Modern Home RoscoeVillage/Wrigley Free St Parking
You have the entire first-floor unit of the house in a safe, clean, and quiet Roscoe Village with shops and restaurants. 5 miles to downtown Chicago by L or car, 5 minutes walk to Brown-line Paulina station, and 20 minutes walk to Wrigley Field. This place provides comforts with an open-concept kitchen, full laundry, etc. whether you travel for leisure, visit friends/family, or work. Fast-speed WIFI and Roku Streaming. Complimentary Starbucks coffee beans for freshly brewing coffee.
$75 per night

Popular amenities for Chicago house rentals

House rentals with a pool

Guest favorite
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
$592 per night
Guest favorite
Home in Grayslake
Huge Indoor Pool &Theater - link moved see details
$770 per night
Guest favorite
Home in McHenry
Highwood Haven
$786 per night
Guest favorite
Home in Chicago
⭐️ Mario's Pad ⭐️ Arcade, Spa, Pool.
$514 per night
Guest favorite
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
$266 per night
Guest favorite
Home in Oak Lawn
Chi Town Relaxation
$178 per night
Guest favorite
Home in Chicago
Luxury Cabin in Lakeview
$943 per night
Guest favorite
Home in Glen Ellyn
Glen Ellyn Home
$443 per night
Guest favorite
Home in McHenry
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
$447 per night
Superhost
Home in Lake Forest
Beautiful 137 Year Old Farm Home (3night min)
$700 per night
Superhost
Home in Wonder Lake
Great girlfriend getaway with jacuzzi tub and pool
$160 per night
Superhost
Home in Evanston
Beautiful Historic Colonial
$1,000 per night

Weekly house rentals

Guest favorite
Home in Chicago
Private 3rd Floor Apartment
Jan 6 – 13
$109 per night
Guest favorite
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Apr 29 – May 6
$117 per night
Guest favorite
Home in Chicago
Wrigleyville Southport Studio
Nov 3 – 10
$138 per night
Guest favorite
Home in Chicago
Cozy garden apartment historic Jackson Bvld.
Nov 29 – Dec 4
$157 per night
Guest favorite
Home in Chicago
The Avondale Guesthouse
Oct 1 – 8
$85 per night
Guest favorite
Home in Chicago
Paradise on the Park
Aug 25 – Sep 1
$147 per night
Guest favorite
Home in Chicago
Chicago Riverhouse modern home near Northeastern
Aug 15 – 22
$304 per night
Guest favorite
Home in Chicago
Cool Quiet Coach House W/ Private Access and Outdoor Space
Dec 31 – Jan 7
$197 per night
Guest favorite
Home in Chicago
The Evergreen House
Mar 17 – 24
$104 per night
Guest favorite
Home in Chicago
Spacious Two Story Luxurious Home w/Outdoor Deck!
Dec 5 – 12
$300 per night
Superhost
Home in Chicago
Lincoln Park - DePaul House w/Patio Free Parking
Apr 4 – 11
$213 per night
Guest favorite
Home in Chicago
Historic Old Town, Fabulous 4 Bedroom Home
Sep 4 – 11
$386 per night

Private house rentals

Superhost
Home in Chicago
Bucktown Home W/ Free Garage Parking for 2 Cars!
$86 per night
Guest favorite
Home in Chicago
*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN
$72 per night
Guest favorite
Home in Mundelein
By Naval Base! Stylish Getaway w Netflix, Games, WiFi, Parking
$135 per night
Superhost
Home in Chicago
Exclusive and Spacious Pilsen Guest House
$48 per night
Guest favorite
Home in Chicago
Chicago getaway for two!
$62 per night
Guest favorite
Home in Berwyn
Retro Modern Bungalow | fire pit | free parking
$115 per night
Superhost
Home in Chicago
Sunny Character-Filled Apartment in Trendy Ukrainian Village
$101 per night
Guest favorite
Home in Chicago
Entire house in Lakeview with yard and garage
$120 per night
Guest favorite
Home in Oak Park
Clean, Cozy Duplex with Kitchen & Free Parking
$109 per night
Guest favorite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
$109 per night
Superhost
Home in Chicago
LAVISH LINCOLN PARK Home w/ Patio +attached garage
$155 per night
Guest favorite
Home in Chicago
2BD/1 BA with summer patio in quiet Roscoe Village
$90 per night

Quick stats about house rentals in Chicago

Total rentals

1.8K properties

Rentals with dedicated workspaces

1.2K properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

450 properties allow pets

Family-friendly rentals

970 properties are a good fit for families

Total number of reviews

68K reviews

Destinations to explore

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  3. Illinois
  4. Cook County
  5. Chicago
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