Short-term rentals Chicago: Cabins, Airbnb & Condos

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

1,254 accommodations in Chicago

Book your Chicago vacation rentals from 1,254 short-term rentals listings. Compare top rentals sites such as Vrbo, Booking.com, Homestay and more on Likibu, the world’s largest rentals Meta search.

  1. Hotel 1 bedroom, with jacuzzi

    Chicago, Illinois

    • 52m²
    • 2
    • 1
    • 1

    4.6      170 Reviews

    From

    $153

    / night

  2. Apartment 2 bedrooms, with air conditioning

    Chicago, Illinois

    • 69m²
    • 5
    • 2
    • 1

    4.5      58 Reviews

    From

    $125

    / night

  3. House 3 bedrooms, with garden

    Chicago, Illinois

    • 167m²
    • 10
    • 3
    • 1

    4.7      56 Reviews

    From

    $53

    / night

  4. Free cancellation
    Bed and breakfast 3 bedrooms, with garden

    Chicago, Illinois

    • 204m²
    • 8
    • 3
    • 2

    5.0      114 Reviews

    From

    $163

    / night

  5. Hotel 1 bedroom, with gym

    Chicago, Illinois

    • 73m²
    • 4
    • 1
    • 1

    4.3      11 Reviews

    From

    $110

    / night

  6. Ad
    Dreaming of a getaway?

    Chicago, United States

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  7. Free cancellation
    Bed and breakfast 5 bedrooms, with garden

    Chicago, Illinois

    • 186m²
    • 9
    • 5
    • 2

    5.0      126 Reviews

    From

    $161

    / night

  8. Room 7 guests, with wifi

    Chicago, Illinois

    • 7
    • 4
    • 1

    5.0      50 Reviews

    From

    $34

    / night

  9. Hostel 1 bedroom, with air conditioning

    Chicago, Illinois

    • 27m²
    • 1
    • 1

    4.1      602 Reviews

    From

    $22

    / night

  10. Hotel 1 bedroom, with air conditioning

    Chicago, Illinois

    • 55m²
    • 2
    • 1
    • 1

    4.0      4 Reviews

    From

    $95

    / night

  11. Free cancellation
    Bed and breakfast 6 guests, with garden

    Chicago, Illinois

    • 6
    • 2

    5.0      72 Reviews

    From

    $161

    / night

  12. Room 12 guests, with garden

    Chicago, Illinois

    • 12
    • 5
    • 1

    5.0      13 Reviews

    From

    $43

    / night

More results in Chicago

Top tips to check out before booking a vacation rental in Chicago


Vacation rental prices and availability in Chicago

Average price per night in Chicago

  • $237Jan
  • $273Feb
  • $385Mar
  • $357Apr
  • $364May
  • $424Jun
  • $436Jul
  • $436Aug
  • $455Sep
  • $357Oct
  • $239Nov
  • $233Dec

Vacation rentals that are available in Chicago (%)

  • 65%Jan
  • 64%Feb
  • 53%Mar
  • 51%Apr
  • 51%May
  • 45%Jun
  • 45%Jul
  • 38%Aug
  • 33%Sep
  • 13%Oct
  • 46%Nov
  • 60%Dec

Frequently Asked Questions about Chicago vacation rentals


Book a vacation rental in Chicago from top accommodation sites, such as Airbnb, Booking.com, VRBO, Expedia and Tripadvisor.


Best vacation accommodations in Chicago

Airbnb, apartments and houses with terrace or balcony in Chicago

Apartment 2 bedrooms, with garden

Chicago, Illinois

  • 130m²
  • 5
  • 2
  • 1

4.3      19 Reviews

From

$139

/ night

Apartment 3 bedrooms, with garden

Chicago, Illinois

  • 111m²
  • 6
  • 3
  • 1

4.7      33 Reviews

From

$130

/ night

Apartment 1 bedroom, with pool

Chicago, Illinois

  • 3
  • 1
  • 1

 

From

$125

/ night

Apartment 5 bedrooms, with air conditioning

Chicago, Illinois

  • 60m²
  • 10
  • 5

4.2      23 Reviews

From

$95

/ night

Apartments and vacation homes with fireplace in Chicago

Apartment 3 bedrooms, with pool

Chicago, Illinois

  • 167m²
  • 8
  • 3
  • 3

5.0      3 Reviews

From

$186

/ night

Apartment 3 bedrooms, with pool

Chicago, Illinois

  • 167m²
  • 8
  • 3
  • 3

4.7      3 Reviews

From

$192

/ night

Free cancellation
Apartment 1 bedroom, with garden

Chicago, Illinois

  • 5
  • 1
  • 1

5.0      31 Reviews

From

$284

/ night

Apartment 2 bedrooms, with air conditioning

Chicago, Illinois

  • 7
  • 2
  • 1

5.0      1 Reviews

From

$98

/ night

Houses, apartments and airbnb with wifi in Chicago to stay connected

Bed and breakfast 1 bedroom, with garden

Chicago, Illinois

  • 20m²
  • 2
  • 1
  • 1

4.3      16 Reviews

From

$136

/ night

Apartment 3 bedrooms, with gym

Chicago, Illinois

  • 220m²
  • 8
  • 3
  • 2

4.5      7 Reviews

From

$348

/ night

Apartment 1 bedroom, with pool

Chicago, Illinois

  • 98m²
  • 4
  • 1
  • 1

5.0      146 Reviews

From

$81

/ night

Room 2 guests, with wifi

Chicago, Illinois

  • 2
  • 1
  • 1

5.0      5 Reviews

From

$45

/ night

Condos and holiday apartment rentals in Chicago

Apartment 3 bedrooms, with air conditioning

Chicago, Illinois

  • 50m²
  • 5
  • 3
  • 1

3.8      15 Reviews

From

$84

/ night

Free cancellation
Apartment 2 bedrooms, with jacuzzi

Chicago, Illinois

  • 111m²
  • 6
  • 2
  • 2

4.7      104 Reviews

From

$248

/ night

Apartment 1 bedroom, with wifi

Chicago, Illinois

  • 50m²
  • 5
  • 1

4.4      10 Reviews

From

$64

/ night

Apartment 2 bedrooms, with wifi

Chicago, Illinois

  • 30m²
  • 9
  • 2
  • 1

4.7      3 Reviews

From

$67

/ night


Vacation rentals in the United States


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, airbnb, 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 1,254 accommodations and book your holiday home, vacation rental or airbnb 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!


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