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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The Avondale Guesthouse

Chicago

Located in Chicago, 4.5 km from Wrigley Field and 5.8 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi.

d
de la Fuente
From
United States
Everything was perfect. Very reccomendable
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 132 reviews
Price from
US$136.12
1 night, 2 adults

Forrestville Ave Large Suite

Bronzeville, Chicago

Located in Chicago, 2.3 km from Oakwood Beach and 3.8 km from Guaranteed Rate Field, Forrestville Ave Large Suite provides accommodation with free WiFi in a historic building.

Z
Zhang
From
Canada
15 mins to green line CTA station. Reasonable space for street parking. Safe neighborhoods. Very comfortable living room, bedroom and washroom.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 106 reviews
Price from
US$126
1 night, 2 adults

Ray's Bucktown Bed and Breakfast

Logan Square, Chicago

Ray's Bucktown Bed and Breakfast provides a sauna and free private parking, and is within 4.9 km of Lincoln Park Zoo and 5.1 km of Wrigley Field.

i
idan
From
Belgium
every thing was above my expectations super nice location amazing breakfast and super kind owner and crew
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 182 reviews
Price from
US$199.19
1 night, 2 adults

Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

In the Old Town district of Chicago, close to 360 Chicago, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace features a garden and a washing machine.

G
Giovanni
From
Italy
Breakfast was amazing, the 0lace is super and location is great, with free and efficient parking. Great service also
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 29 reviews
Price from
US$419
1 night, 2 adults

4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome

Near North Side, Chicago

Boasting a patio with city views, a garden and barbecue facilities, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome can be found in Chicago, close to Oak Street Beach and 2.2...

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
Price from
US$499
1 night, 2 adults

The Polo Inn Bridgeport U.S.A.

Bridgeport, Chicago

Situated within 1.8 km of Guaranteed Rate Field and 6.1 km of Field Museum Of Natural History, The Polo Inn Bridgeport U.S.A. Features rooms with air conditioning and a private bathroom in Chicago.

O
Omar Leon
From
Mexico
I really enjoyed the whole experience. The breakfast was simply delicious. Excellent attention and service. The room is lovely and warm.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 46 reviews
Price from
US$285
1 night, 2 adults

Villa D' Citta

Lincoln Park, Chicago

Set just 2.2 km from North Avenue Beach, Villa D' Citta offers accommodation in Chicago with access to a tennis court, barbecue facilities, as well as a lift.

C
Carrie
From
United States
The beautiful courtyard where I ate breakfast, and sitting with my mug of tea on the upper deck. Beautiful old home. I also liked that the kitchen was fully available, and preparing breakfast from all the options set out and in the fridge felt like I was part of a home. You can easily make a packed lunch to take with. Really liked the large walk-in shower, and having a bottle of water available in the room. The hosts were very attentive. It is a great location with very convenient access to Fullerton Station, and right next to the DePaul University campus.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 32 reviews
Price from
US$205.85
1 night, 2 adults

Sentral Michigan Avenue

Hotel in Chicago Loop, Chicago

Sentral Michigan Avenue has a fitness centre, garden, a shared lounge and restaurant in Chicago. This 3-star hotel offers a shared kitchen, a 24-hour front desk and free WiFi.

F
Fany
From
Israel
Great deal! Excellent location, great room with everything you could ask for, including washing machine and dryer. Absolutely spacious. Very clean. Parking is costly for those coming with a car - the location is so central that there is no need for a car. Highly recommended.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,051 reviews
Price from
US$169
1 night, 2 adults

Sonder by Marriott Bonvoy The Burnham Apartments Loop

West Loop, Chicago

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.

J
Jeroen
From
Netherlands
I stayed at Sonder The Burnham for 3 weeks and had a great stay. It's located in the middle of Downtown Chicago close to Union Station. I had a large clean apartment with all the amenities I needed. There's a large well-equipped kitchen, a washer/dryer, quiet air conditioner and a great bed. It was clean and there was not too much noise from the street, which can be an issue in Chicago, with the elevated metro lines. Large screen with Roku tv or HDMI connection and good Wi-Fi. Little to complain about, highly recommended!
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 368 reviews
Price from
US$218.45
1 night, 2 adults

Sonder by Marriott Bonvoy The Opal Apartments River North

River North, Chicago

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.

M
Mircea-Dan
From
Austria
Great facility, modern equipment and located very close to tourist attractions.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 343 reviews
Price from
US$224.40
1 night, 2 adults
All holiday rentals in Chicago

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

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

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 370 reviews

    Situated in Chicago, within 2.2 km of Ohio Street Beach and 600 metres of Chicago Board of Trade Building, The Plymouth, Sonder Apartments by Marriott Bonvoy features free WiFi.

    From US$225.24 per night
  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 145 reviews

    In the West Loop district of Chicago, close to Union Station, Sonder by Marriott Bonvoy Greektown Apartments has free WiFi and a washing machine.

    From US$194.39 per night
  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 506 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.

  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 301 reviews

    Located within 1.1 km of United Center and 2.8 km of Union Station, Sonder by Marriott Bonvoy Market Hall Apartments West Loop provides rooms with air conditioning and a private bathroom in Chicago.

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 471 reviews

    Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, a microwave and a...

  • Located in the centre of Chicago, 2.5 km from Ohio Street Beach, Loop 1BR w Lounge Rooftop nr Art Institute CHI-103 provides air-conditioned accommodation with free WiFi and a TV.

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 53 reviews

    Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop features accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a...

  • Located in the centre of Chicago, 2.8 km from Ohio Street Beach, Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382 provides air-conditioned accommodation with free WiFi and a TV.

Holiday Rentals with swimming pools in Chicago and nearby

Highly rated holiday rentals in Chicago and nearby

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

    Featuring garden views, Wicker Park Inn offers accommodation with patio, around 3.6 km from United Center. The 3-star bed and breakfast has air-conditioned rooms with a private bathroom and free WiFi.

    From US$303.50 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 156 reviews

    Located within 2.8 km of Oakwood Beach and 1.4 km of Guaranteed Rate Field in Chicago, McCormick Place Guest House provides accommodation with seating area.

    From US$154 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 327 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.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 41 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 8.8
    Fabulous - What previous guests thought, 49 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 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 8.8
    Fabulous - What previous guests thought, 22 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.

Enjoy breakfast in Chicago and nearby

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

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  • Avg. price/night: US$317.73
    Scored out of 10, guest rating 9.6
    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
  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 301 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple
  • Avg. price/night: US$317.73
    Scored out of 10, guest rating 9.6
    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