The 10 best vacation rentals in Chicago, US | Booking.com
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Vacation Rentals in Chicago

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The best vacation rentals in Chicago

Check out our selection of great vacation rentals in Chicago

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Most booked vacation rentals in Chicago and surrounding area in the past month

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These vacation rentals in Chicago and nearby have options with free cancellation

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 469 reviews

    Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, a microwave, and a...

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 147 reviews

    Sonder by Marriott Bonvoy Greektown Apartments enjoys a location in Chicago, 1.3 miles from Art Institute of Chicago and one mile from DePaul University. This 4-star condo hotel offers free Wifi.

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 289 reviews

    Sonder by Marriott Bonvoy Market Hall Apartments West Loop offers accommodations in Chicago, a 13-minute walk from United Center and 1.7 miles from Union Station.

  • Loop 1BR w Lounge Rooftop nr Art Institute CHI-103 offers accommodations in Chicago, a 1-minute walk from Chicago Symphony Orchestra and half a mile from Willis Tower.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 47 reviews

    Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster,...

  • Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382 offers accommodations in Chicago, a 11-minute walk from Cloud Gate – The Bean and half a mile from Chicago Symphony Orchestra.

  • Loop 2BR w Gym Doorman same block as L CHI-674 is located in Chicago, just a 7-minute walk from Chicago Symphony Orchestra and 0.4 miles from Willis Tower.

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 366 reviews

    Located in Chicago, within 1.4 mi of Ohio Street Beach and 1969 feet of Chicago Board of Trade Building, The Plymouth, Sonder Apartments by Marriott Bonvoy features free WiFi.

Enjoy breakfast in Chicago and nearby

  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 45 reviews

    Wicker Park Inn enjoys a location in Chicago, 2.3 miles from United Center and 2.8 miles from Water Tower Chicago.

    From $368.57 per night

  • Loop Studio w gym pool lounge 1 block from L CHI-694 features accommodations in the center of Chicago, 1.5 miles from Ohio Street Beach and a 11-minute walk from Willis Tower.

  • Just a 15-minute walk from Millennium Park and 0.9 miles from DePaul University, Loop 1BR w Gym Pool WD nr Financial District CHI-222 features accommodations in Chicago with a shared lounge.

  • Loop 1BR w Fitness center nr W Loop the L CHI-194 offers accommodations in Chicago, a 15-minute walk from Grant Park and 0.7 miles from Art Institute of Chicago.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 100 reviews

    Located in the heart of downtown Chicago, just 3 blocks away from the Magnificent Mile, this self-catering apartment features a balcony with iconic views of the city. Free WiFi access is available.

  • Streeterville 1BR w Pool Deck nr Beach Park CHI-585 offers accommodations in the center of Chicago, a 4-minute walk from Ohio Street Beach and half a mile from Shops at Northbridge.

  • Streeterville 2BR w Deck Gym nr Beach Park CHI-589 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 331 reviews

    Sonder by Marriott Bonvoy The Opal Apartments River North features accommodations within 0.4 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

Highly rated vacation rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 106 reviews

    Forrestville Ave Large Suite is located in Chicago, just 2.8 miles from Museum of Science and Industry - Chicago and 4.5 miles from Field Museum of Natural History.

  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 320 reviews

    Just a 18-minute walk from Art Institute of Chicago and 0.9 miles from Chicago Symphony Orchestra, Kasa South Loop Chicago features accommodations in Chicago, with a shared lounge.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 33 reviews

    The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile is an apartment featuring rooms with free Wifi and air conditioning in the center of Chicago.

  • Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 45 reviews

    Aurelien Spacious Apartments in the Heart of Gold Coast provides accommodations within 0.7 miles of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster, and a fridge.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 17 reviews

    Just a 19-minute walk from Union Station and 1.2 miles from Willis Tower, K2 Sky High Apartments with Stunning Chicago Views in West Loop features accommodations in Chicago, with a shared lounge.

  • Scored out of 10, guest rating 8.2
    Very Good - What previous guests thought, 524 reviews

    Sonder by Marriott Bonvoy South Wabash Apartments South Loop offers accommodations in Chicago, 1.2 miles from Art Institute of Chicago and 1.2 miles from Chicago Symphony Orchestra.

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

  • Scored out of 10, guest rating 8.5
    Very Good - What previous guests thought, 20 reviews

    Studio flat in the heart of Downtown Chicago offers accommodations in Chicago, a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

FAQ about vacation rentals in Chicago

Vacation Rentals That Guests Love in Chicago

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  • Villa Dubois Guest House

    Vacation Rental in Bronzeville, Chicago
    Avg. price/night: $231.67
    Scored out of 10, guest rating 6.5
    Pleasant - What previous guests thought, 216 reviews
    Im so happy i came across Villa Dubois Guesthouse. The whole property is clean and organized, free street parking, neighborhood is quiet. I love the full functional kitchen where you can prepare meals.security cameras around the common area for safety.If you dont mind sharing a space with strangers,this a nice budget friendly place to stay😊
    Guest review by
    LIW-LIWA
    Young couple

  • Villa D' Citta

    Vacation Rental in Lincoln Park, Chicago
    Avg. price/night: $317.73
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 32 reviews
    Rosa & Edith were attentive to our needs and expectations. The entire staff was friendly, accommodating and engaging. The Villa was at our disposal, and we were able to enjoy the amenities with our daughter and her husband who live nearby.
    Guest review by
    Nosal
    Young couple

  • Sonder by Marriott Bonvoy Market Hall Apartments West Loop

    Vacation Rental in West Loop, Chicago
    Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 289 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple

  • Villa D' Citta

    Vacation Rental in Lincoln Park, Chicago
    Avg. price/night: $317.73
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 32 reviews
    The Villa is lovely and the host was great. They have great options for breakfast which you prepare yourself. Location was really nice - lovely the neighborhood. Loved the wine on tap!
    Guest review by
    Sydney
    Group