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

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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.

G
Gonzalez
From
Colombia
The location was perfect, it was also very clean and the owner was really very attentive, I would recommend it
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 132 reviews
Price from
US$136.12
1 night, 2 adults
Check availability

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, 189 reviews
Price from
US$199.19
1 night, 2 adults
Check availability

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.

M
Martinusz
From
Belgium
Walkable location, well equipped. Inna, our host, was exceptionally helpful with tips and ideas and she was always available for communication.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 29 reviews
Price from
US$419
1 night, 2 adults
Check availability

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
Check availability

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 9.1
Superb - What previous guests thought, 48 reviews
Price from
US$285
1 night, 2 adults
Check availability

Sentral Michigan Avenue

Chicago Loop, Chicago

Set in Chicago, 800 metres from Grant Park and 1.8 km from the centre, Sentral Michigan Avenue offers air-conditioned accommodation with free WiFi, and an infinity pool.

a
asma al hammadi
From
United Arab Emirates
The rooms are incredibly spacious, and it is the same price as nearby hotel for double the space. Definetly worth your money.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,045 reviews
Price from
US$169
1 night, 2 adults
Check availability

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.

A
Ansis
From
United States
A fantastic property, a great location! The coffee and tea upon arrival was a nice touch. A very quiet, secure location, tastefully decorated apartment. I will be recommending The Burnham to my colleagues and friends as the place to stay in Chicago!
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 357 reviews
Price from
US$228.65
1 night, 2 adults
Check availability

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.

S
Sara
From
France
I really liked the size, the amenities, the fact that it wasn’t a hotel and where it was located. And I always felt safe!
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 338 reviews
Price from
US$186.15
1 night, 2 adults
Check availability

Cubs! Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans!

Lakeview, Chicago

In the Lakeview district of Chicago, close to Wrigley Field, Cubs! Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans! has free WiFi and a washing machine.

P
Pudvah
From
United States
Location was absolutely unbeatable if you're hitting a Cubs game or Wrigleyville in general. Host was very communicative and was easily reachable. Parking pass in Wrigleyville was a huge benefit and was included in the rental.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 327 reviews
Price from
US$206.40
1 night, 2 adults
Check availability

5430 Happy Home

Chicago

Set within 4.5 km of Museum of Science and Industry - Chicago and 4.8 km of Guaranteed Rate Field in Chicago, 5430 Happy Home offers accommodation with free WiFi and seating area.

A
Aleksandr Sizganov
From
Russia
very comfortable. hospitable hosts. All liked it. Thank you!
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 385 reviews
Price from
US$88
1 night, 2 adults
Check availability
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 7.7
    Good - What previous guests thought, 146 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$361.79 per night
  • Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 295 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.

    From US$204.67 per night
  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 464 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...

    From US$225.24 per night

  • 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 8.6
    Fabulous - What previous guests thought, 50 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.

  • Situated right in the heart of Chicago, 2.9 km from Ohio Street Beach, Loop 2BR w Gym Doorman same block as L CHI-674 features air-conditioned accommodation with free WiFi and a TV.

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 365 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$286.95 per night

Highly rated holiday rentals in Chicago and nearby

  • 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.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 338 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.

    From US$225.24 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 324 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, 38 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 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.

Enjoy breakfast in Chicago and nearby

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, 222 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
    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$204.67
    Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 295 reviews
    Looks like a vacation house
    Guest review by
    Linh
    Young couple

  • Villa D' Citta

    Holiday Rental in Lincoln Park, Chicago
    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