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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2F Chicago's Little Italy near West Loop & Downtown

Chicago

Offering quiet street views, 2F Chicago's Little Italy near West Loop & Downtown is an accommodation situated in Chicago, 3.1 km from Willis Tower and 4.2 km from Depaul University.

G
GRETA
From
Lithuania
Very nice property owner, spacious place, a lot of additional advantages: coffee mashine, snacks, hygiene products, washing mashine and a dryer.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 176 reviews
Price from
US$225
1 night, 2 adults
Check availability

The Sono Chicago

Near North Side, Chicago

The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 1.2 km away. Parking is free with permit provided by The Sono Chicago.

B
Belen Ladaga
From
Argentina
Staff was super friendly and nice, always willing to help. Breakfast 10/10, a lot of options and very yummy. The style of the hotel is amazing, and very cosy. We used the shared spaces a lot and always felt confortable. I woul ddefinitely stay here again!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 317 reviews
Price from
US$272.40
1 night, 2 adults
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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.

g
gonzalo
From
South Korea
location was amazing, breakfast was great.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 187 reviews
Price from
US$191.99
1 night, 2 adults
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Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub

Chicago

A recently renovated holiday home situated in Chicago, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub features a garden.

K
Kylie
From
United States
Loved the location/neighborhood with proximity to the downtown area but privacy while spending time at the house. The size is great, outside property very nice. Plenty of street parking for folks who drive, but easy public transportation access for folks who use that to get in/around.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews
Price from
US$450
1 night, 2 adults
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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
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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
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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$270
1 night, 2 adults
Check availability

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 9.5
Exceptional - What previous guests thought, 32 reviews
Price from
US$205.85
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.

M
Mohamed
From
Saudi Arabia
Excellent location, superb view, nice staff, comfortable bed and sofa, well equipped kitchen and modern apartment.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,048 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.

광
광옥
From
Mexico
Everything exceeded my expectations and I was satisfied.
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 349 reviews
Price from
US$237.15
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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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$368.57 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 47 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...

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 101 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, 331 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.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 320 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 8.1
    Very good - What previous guests thought, 349 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 9.3
    Superb - What previous guests thought, 32 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.

Enjoy breakfast in Chicago and nearby

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, 147 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.

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

  • 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.

  • 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...

  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 4 reviews

    An apartment nestled in the centre of Chicago, Jeffjack Heated Pool Penthouse in Chicago's West Loop features private parking, free WiFi, a rooftop pool and fitness centre.

  • Situated in Chicago, 1.1 km from Union Station and 1.4 km from Willis Tower, W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-646 offers a rooftop pool and air conditioning.

  • River N Studio w Gym Pool nr L stop CHI-366

    Chicago
    Free cancellation options available

    Located in a central area of Chicago, 1.3 km from Oak Street Beach, River N Studio w Gym Pool nr L stop CHI-366 provides air-conditioned accommodation with free WiFi and a TV.

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 6.5
    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

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

    Holiday 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

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

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Hotels near Union Station

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Hotels in River North

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