Short-term rentals in Chicago: apartment and room for rent

Find your holiday rentals in Chicago: house, apartment, villa and any accommodation for rent

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1188 accommodations in Chicago

Book your Chicago vacation rentals from 1188 short-term rentals listings. Compare top rentals sites such as Booking.com, HomeAway, TripAdvisor and more on Likibu, the world’s largest rentals Meta search.

  1. From
    $171/ night
    Apartment with pool, 1 bedroom
    Booking.com
    • 22 guests
    • 1Bedrooms : 1
    • 1Bathrooms : 1
    •  
    4.95 / 5-
  2. From
    $160/ night
    Apartment with pool, 1 bedroom
    Booking.com
    • 22 guests
    • 1Bedrooms : 1
    •  
    4.75 / 5-
  3. From
    $127/ night
    Apartment with air conditioning, 3 bedrooms
    Booking.com
    • 1010 guests
    • 3Bedrooms : 3
    • 2Bathrooms : 2
    •  
    4.7 / 5-
  4. From
    $99/ night
    Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
    HomeAway
    • 111 m²
    • 66 guests
    • 2Bedrooms : 2
    • 1Bathrooms : 1
    •  
    4.98 / 563 Reviews
  5. From
    $88/ night
    House with garden, 3 bedrooms
    Booking.com
    • 88 guests
    • 3Bedrooms : 3
    • 1Bathrooms : 1
    •  
    4.7 / 5-
  6. Ad
    From
    $35/ night
    Live there. Book unique homes.
    Airbnb
    • Search on Airbnb - Chicago
  7. From
    $149/ night
    Chicago Guest House | Discover Vibrant Wrigleyville From This Captivating Home!
    HomeAway
    • 186 m²
    • 99 guests
    • 5Bedrooms : 5
    • 2Bathrooms : 2
    •  
    4.98 / 5108 Reviews
  8. From
    $160/ night
    Apartment with jacuzzi, 1 bedroom
    Booking.com
    • 22 guests
    • 1Bedrooms : 1
    • 1Bathrooms : 1
    •  
    4.75 / 5-
  9. From
    $101/ night
    Sonder | Wrigley Field | Stunning 3BR + Balcony
    TripAdvisor
    • 88 guests
    • 3Bedrooms : 3
    • 2Bathrooms : 2
    •  
    ? / 5 
  10. From
    $88/ night
    Sonder | Wrigley Field | Beautiful 3BR + Balcony
    TripAdvisor
    • 88 guests
    • 3Bedrooms : 3
    • 2Bathrooms : 2
    •  
    5 / 51 Reviews
  11. From
    $98/ night
    Apartment with pool, 2 bedrooms
    Booking.com
    • 66 guests
    • 2Bedrooms : 2
    • 2Bathrooms : 2
    •  
    4.5 / 5-
  12. From
    $149/ night
    Nowhere Will You Feel More at Home! | Chicago Guest House LLC | Wrigleyville
    HomeAway
    • 112 m²
    • 66 guests
    • 3Bedrooms : 3
    • 2Bathrooms : 2
    •  
    4.97 / 560 Reviews
More results in Chicago

Book Chicago vacation rentals from top accommodation sites.

Best vacation accommodations in Chicago

Apartments and Houses with terrace or balcony in Chicago

From
143€/ night
FAMILY FRIENDLY, CONVENIENT NORTHCENTER NEIGHBORHOOD, BEAUTIFUL 2 BDRM. FRE
HomeAway
  • 74 m²
  • 55 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.92 / 526 Reviews
From
107€/ night
NEW LISTING! City gem w/ gym- walk to shopping/dining
TripAdvisor
  • 66 guests
  • 2Bedrooms : 2
  • 2Bathrooms : 2
  •  
? / 5 
From
162€/ night
NEW LISTING! Fifth-floor retreat with private balcony and gym!
TripAdvisor
  • 44 guests
  • 2Bedrooms : 2
  • 2Bathrooms : 2
  •  
? / 5 
From
103€/ night
Apartment with gym, 2 bedrooms
Booking.com
  • 66 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.5 / 5-

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Apartments and vacation homes with fireplace in Chicago

From
90€/ night
Great Location!! Roscoe Village, Lakeview, Close to Wrigley
HomeAway
  • 121 m²
  • 88 guests
  • 3Bedrooms : 3
  • 2Bathrooms : 2
  •  
4.95 / 519 Reviews
From
88€/ night
SPRING PRICING SPECIAL! Visit me April-May!!
HomeAway
  • 102 m²
  • 44 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.9 / 520 Reviews
From
152€/ night
Luxury rental w/ fitness room & skyline views!
TripAdvisor
  • 88 guests
  • 2Bedrooms : 2
  • 3Bathrooms : 3
  •  
? / 5 
From
89€/ night
Roscoe Village, Modern, Lakeview, Close to Cubs, $99 winter special~Cozy
HomeAway
  • 66 guests
  • 2Bedrooms : 2
  • 2Bathrooms : 2
  •  
4.85 / 513 Reviews

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Houses and apartments with wifi in Chicago to stay connected

From
126€/ night
Apartment with sea view, 2 bedrooms
Booking.com
  • 55 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.3 / 5-
From
134€/ night
Apartment with pool, 1 bedroom
Booking.com
  • 33 guests
  • 1Bedrooms : 1
  • 1Bathrooms : 1
  •  
4.4 / 5-
From
134€/ night
Chicago Guest House | Wrigleyville | Character You Won't Find Anywhere Else!
HomeAway
  • 111 m²
  • 66 guests
  • 3Bedrooms : 3
  • 2Bathrooms : 2
  •  
4.89 / 59 Reviews
From
113€/ night
Apartment with pool, 1 bedroom
Booking.com
  • 33 guests
  • 1Bedrooms : 1
  • 1Bathrooms : 1
  •  
4.3 / 5-

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Condos and holiday apartment rentals in Chicago

From
135€/ night
Wrigleyville | Chicago Guest House | Not Just A Vacation Rental; A Real Home!
HomeAway
  • 204 m²
  • 88 guests
  • 3Bedrooms : 3
  • 2Bathrooms : 2
  •  
4.98 / 5109 Reviews
From
120€/ night
Apartment with gym, 1 bedroom
Booking.com
  • 33 guests
  • 1Bedrooms : 1
  • 1Bathrooms : 1
  •  
4.35 / 5-
From
117€/ night
Apartment with pool, 2 bedrooms
Booking.com
  • 55 guests
  • 2Bedrooms : 2
  • 1Bathrooms : 1
  •  
4.45 / 5-
From
104€/ night
Sonder | Roscoe | Beautiful 3BR + Terrace
TripAdvisor
  • 77 guests
  • 3Bedrooms : 3
  • 3Bathrooms : 3
  •  
? / 5 

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Book your Chicago accommodation: house, apartment, private room short-term rentals

Compare all short-term rentals in Chicago from the best vacation rental websites. Thanks to Likibu, you can easily book your apartment rental, house rental or villa with pool in Chicago. Just select the lodging you would like to stay at during your vacation in in Illinois. You can find last minute bookings for a week-end to enjoy the luxury of a a home away from home in in the United States.

Compare 1188 accommodations and book your holiday rental or vacation rental in Chicago now. You'll never stay at a hotel again! Find the best deals on a guesthouse or private room in in Illinois. Benefit from a full apartment in Chicago and enjoy as much as you can your trip in in the United States!

Vacation rentals near Chicago