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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.

Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOST
Entire apartment · 2 guests · 2 beds · 1 bath

Basement Studio w/Free St. Parking, Humboldt ParkLocated in Humboldt Park, 6 miles from downtown, this basement studio is perfect for a stay in Chicago. We are located on a strip with approximately 11 houses and no houses across. There is a lot of Park area. At night it's a quiet neighborhood. We are located half a block away from the bus to Navy Pier, approx. 45 minutes to get to Navy Pier. There is free street parking available with NO parking permit required. There is a pool (only in summer) and park access half a block away.

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).

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

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Popular apartment amenities in Chicago

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

Houses in Chicago

  1. Private room
  2. Chicago
Bucktown - Private Room
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
SUPERHOST
  1. Entire house
  2. Chicago
Private Andersonville Guest Suite
SUPERHOST
  1. Private room
  2. Chicago
Logan Square Vintage Deluxe Private Suite & Bath
SUPERHOST
  1. Private room
  2. Chicago
Private Bed and Bathroom in a Great Location
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
  1. Entire house
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard
SUPERHOST
  1. Private room
  2. Chicago
Self check in near Downtown Chicago
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
SUPERHOST
  1. Private room
  2. Evanston
A place for scholars & solo adventurers w/parking
  1. Entire house
  2. Chicago
Newly Renovated 2br, 1 ba- Logan Square

Pet-friendly apartments

SUPERHOST
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  2. Chicago
Susie's Sanctuary- Pet friendly +parking
  1. Entire apartment
  2. Chicago
Trendy Wicker Park with parking, sleeps up to 5
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  2. Forest Park
Cute 1 bedroom near Blue line
SUPERHOST
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  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
SUPERHOST
  1. Entire apartment
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
SUPERHOST
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  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
PLUS
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  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
SUPERHOST
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  2. Chicago
Discover Chicago from a Modern Apartment
SUPERHOST
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  2. Chicago
❤️ Cozy and Comfy 1BR Condo in Logan Square!
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  2. Chicago
New Spot in West Town
SUPERHOST
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  2. Chicago
Entire 1st Floor Apt near O'Hare/ORD & Blue Line
SUPERHOST
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  2. Chicago
Ukrainian Village Garden Retreat

Apartments with WiFi

SUPERHOST
  1. Entire apartment
  2. Chicago
A laid-back studio few minutes from Wrigley Field
  1. Private room
  2. Chicago
Hattie’s House
SUPERHOST
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  2. Chicago
Apartment close to Midway and Downtown! 1bdr, 1bth
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
PLUS
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  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
SUPERHOST
  1. Private room
  2. Chicago
Private Bedroom Near O’hare in Norwood Park
SUPERHOST
  1. Entire apartment
  2. Chicago
Chicago Sanctuary: Perfect 1BD in West Town!
PLUS
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  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOST
  1. Entire apartment
  2. Chicago
Edgewater, private, charming coach house 1 ( of 2)
  1. Entire apartment
  2. Chicago
Discover North Side Chicago from Modern Studio APT
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  2. Chicago
Calming Edgewater Glen Sanctuary
SUPERHOST
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  2. Chicago
Spacious Apartment minutes from Downtown/McCormick

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