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 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.

H
Helena
From
Finland
The staff contacted me before and asked what kind of breakfast I like. Incredibly good service!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 317 reviews
Price from
US$244.80
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.

S
Susie Katja
From
Denmark
amazing breakfast amazing staff
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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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.

S
Søren
From
Denmark
Friendly staff, homey atmosphere, amazing breakfast. Would stay here again!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 48 reviews
Price from
US$270
1 night, 2 adults
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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.

G
Gemma
From
Ireland
The location is perfect, could not be better. The area is very safe. There is a restaurant next door serving breakfast, lunch and dinner, there is a small convenience store / bakery also next door. The property is very secure, also has night time security personnel. The pool and hot tub were lovely. It is within walking distance of all the main tourist attractions and shopping and restaurants.
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.

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, 349 reviews
Price from
US$237.15
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.

M
Michael Haig
From
China
Clean and spacious rooms. Great location.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 331 reviews
Price from
US$229
1 night, 2 adults
Check availability

Cubs Playoffs - 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 Playoffs - 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, 331 reviews
Price from
US$83.85
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, 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, 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, 34 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...

Enjoy breakfast in Chicago and nearby

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

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 468 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...

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

  • 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.

  • 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.

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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