The 10 best holiday rentals in Chicago, USA | Booking.com
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Holiday Rentals in Chicago

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The best holiday rentals in Chicago

Check out our pick of great holiday rentals in Chicago

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Most booked holiday rentals in Chicago and surroundings in the past month

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Enjoy breakfast in Chicago and nearby

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

  • Set in the centre of Chicago, 2.4 km from Ohio Street Beach and less than 1 km from Willis Tower, Loop 1BR w Gym Pool WD nr Financial District CHI-222 offers free WiFi, a shared lounge and air...

  • Located in the centre of Chicago, 300 metres from Willis Tower, Loop 1BR w Fitness center nr W Loop the L CHI-194 provides air-conditioned accommodation with free WiFi and a TV.

  • The Penthouse at Grand Plaza

    River North, Chicago
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Superb - 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.

  • Situated right in the centre of Chicago, 300 metres from Ohio Street Beach, Streeterville 1BR w Pool Deck nr Beach Park CHI-585 features air-conditioned accommodation with free WiFi and a TV.

  • Set in the heart of Chicago, 300 metres from Ohio Street Beach, Streeterville 2BR w Deck Gym nr Beach Park CHI-589 offers air-conditioned accommodation with free WiFi and a TV.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 335 reviews

    Sonder by Marriott Bonvoy The Opal Apartments River North features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

  • Kasa South Loop Chicago

    South Loop, Chicago
    Free cancellation options available
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 322 reviews

    Featuring 4-star accommodation, Kasa South Loop Chicago is located in Chicago, 1.4 km from Willis Tower and 1.3 km from CIBC Theatre.

  • Level Chicago River North

    River North, Chicago
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Set in Chicago and with Oak Street Beach reachable within 2.4 km, Level Chicago River North offers a seasonal outdoor swimming pool, non-smoking rooms, free WiFi throughout the property and a fitness...

Highly rated holiday rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 352 reviews

    Sonder by Marriott Bonvoy The Burnham Apartments Loop offers accommodation within 1.6 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 36 reviews

    Situated conveniently in the centre of Chicago, The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile offers air-conditioned rooms with free WiFi and private parking.

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

    Aurelien Spacious Apartments in the Heart of Gold Coast provides accommodation within 1.1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a toaster and a fridge.

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

    Set 1.6 km from Union Station and 1.9 km from Willis Tower, K2 Sky High Apartments with Stunning Chicago Views in West Loop features free WiFi and units equipped with a kitchen, balcony and seating...

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 525 reviews

    In the South Loop district of Chicago, close to Field Museum Of Natural History, Sonder by Marriott Bonvoy South Wabash Apartments South Loop has free WiFi and a washing machine.

    From US$325.49 per night
  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Right in the centre of Chicago, situated within a short distance of Oak Street Beach and 360 Chicago, Historic luxury Townhouse in Downtown Chicago offers free WiFi, air conditioning and household...

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 21 reviews

    In the Downtown Chicago district of Chicago, close to 360 Chicago, Studio flat in the heart of Downtown Chicago features free WiFi and a washing machine.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 5 reviews

    Right in the heart of Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests has garden views from the balcony.

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

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  • Villa Dubois Guest House

    Holiday Rental in Bronzeville, Chicago
    Avg. price/night: US$231.67
    Scored out of 10, guest rating 6.7
    Pleasant - What previous guests thought, 218 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

    Holiday Rental in Lincoln Park, Chicago
    Avg. price/night: US$345.48
    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

    Holiday Rental in West Loop, Chicago
    Avg. price/night: US$214.96
    Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 292 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple

  • Villa D' Citta

    Holiday Rental in Lincoln Park, Chicago
    Avg. price/night: US$345.48
    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