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Vacation rental apartments in Chicago

Book downtown vacation rental apartments, houses, and more on Airbnb

Top-rated apartments in Chicago

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

Casa de Sueño/Private Bathroom/Near Train/Loyola
Private room · 2 guests · 2 beds · 1 private bath

Casa de Sueño/Private Bathroom/Near Train/LoyolaGuests room includes: Queen sized bed, a spacious desk with office supplies, Mini fridge flat screen TV with Apple TV with free Netflix, you can Stream movies/shows through your Apple device or use one of these converter apps to stream from android: https://letsview.com/mirror-android-to-apple-tv.html Also has an Amazon Firestick and HDMI hookup. Iron/board, closet w/ hangers, sharper image radio/speakers/cd player, basic office supplies. Printer in LR. Free parking with permits (ask).

New Spot in West Town
Entire apartment · 3 guests · 2 beds · 1 bath

New Spot in West TownComfortable spot thats close to downtown, without all the busy cars and street noise! Minutes away from the United Arena, as well as popular neighborhoods such as Wicker Park and South Loop. Guests with canine family members can enjoy a dog park a block away. The home also has smart technology features such as a key on your phone for added security. You can also enjoy great food from local Mexican, pizza, and burger places a short walk away.

Great location. Free parking.  One night available
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Great location. Free parking. One night availableGreat location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Vacation rentals for every style

Get the amount of space that is right for you

  • Apartments
  • Houses
  • Guesthouses

Popular apartment amenities in Chicago

  • Wifi
  • Kitchen
  • Air conditioning
  • Free parking
  • Heating

Houses in Chicago

  1. Private room
  2. Chicago
Bucktown - Private Room
$42 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
$50 per night
SUPERHOST
  1. Private room
  2. Chicago
Logan Square Vintage Deluxe Private Suite & Bath
$70 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
$56 per night
SUPERHOST
  1. Entire house
  2. Chicago
MODERN! 2 BD/2 BA RETREAT IN MT. GREENWOOD/BEVERLY
$114 per night
SUPERHOST
  1. Private room
  2. Chicago
Private, Cozy Bedroom Near O’hare in Norwood Park
$32 per night
  1. Entire house
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard
$100 per night
SUPERHOST
  1. Private room
  2. Chicago
Self check in near Downtown Chicago
$36 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
$41 per night
SUPERHOST
  1. Private room
  2. Oak Park
Antique Filled Home
$65 per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
$29 per night
SUPERHOST
  1. Private room
  2. Evanston
A place for scholars & solo adventurers w/parking
$35 per night

Pet-friendly apartments

SUPERHOST
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  2. Chicago
Susie's Sanctuary- Pet friendly +parking
$119 per night
  1. Entire apartment
  2. Chicago
Trendy Wicker Park with parking, sleeps up to 5
$145 per night
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  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
$78 per night
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  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
$89 per night
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  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
$89 per night
PLUS
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  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
$118 per night
SUPERHOST
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  2. Chicago
Discover Chicago from a Modern Apartment
$138 per night
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  2. Chicago
Roscoe Village One Bed Lux Apartment Near Wrigley
$85 per night
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  2. Chicago
❤️ Cozy and Comfy 1BR Condo in Logan Square!
$97 per night
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  2. Chicago
Ukrainian Village Garden Retreat
$94 per night
  1. Entire apartment
  2. Chicago
Logan Square Historic Getaway
$89 per night
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  2. Forest Park
Village Cottage - Clean & Private, Pets OK
$99 per night

Apartments with WiFi

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  2. Chicago
A laid-back studio few minutes from Wrigley Field
$84 per night
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  2. Chicago
Spacious, light-drenched studio-private entrance!
$81 per night
  1. Private room
  2. Chicago
Hattie’s House
$36 per night
  1. Private room
  2. Chicago
Stylish, Shared Apartment for the Perfect Get Away
$30 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Apartment close to Midway and Downtown! 1bdr, 1bth
$55 per night
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
$20 per night
PLUS
  1. Entire apartment
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
$99 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Chicago Sanctuary: Perfect 1BD in West Town!
$53 per night
SUPERHOST
  1. Entire apartment
  2. Evanston
Charming studio apartment
$90 per night
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  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
$58 per night
  1. Entire apartment
  2. Chicago
Calming Edgewater Glen Sanctuary
$81 per night
  1. Entire apartment
  2. Chicago
Cool and Comfy First Floor in hoppin' Logan Square
$85 per night

Nearby destinations