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.

L
LEO_DOUTLER
From
Canada
Everything was clean , working, and each detail to make your stay more cozy was provided
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 133 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.

H
Howard
From
United Kingdom
Ray's B & B, was great. Full arrival arrangements were relayed to me before I arrived. The place was quirky, clean and the staff were very willing and thoughtful. Everything was thought of to make my stay an enjoyable one.
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$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, 2,050 reviews
Price from
US$169
1 night, 2 adults
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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, 352 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.

E
Eva
From
Germany
The apartment is perfectly located for exploring the city with its nice restaurants, museums and comedy bars. The check-in was easy, all information necessary provided; the house and surrounding area seemed safe. The apartment is as beautiful as on the pictures, great view, modern equipment, comfortable beds. It was nice to have two bathrooms with showers, one bed is in a separate bedroom, one is in a half-detached room in the living area, which was great for our stay. Kitchen is equipped with all appliances you'd need including very nice coffee. Huge fridge and washing machine/dryer available for anyone who plans a longer stay. Can only recommend staying here!
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 335 reviews
Price from
US$340
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, 330 reviews
Price from
US$208.98
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 7.6
    Good - What previous guests thought, 466 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.

    From US$328.09 per night
  • 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 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 7.5
    Good - What previous guests thought, 292 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$214.96 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, 49 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.

Enjoy breakfast 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$354.71 per night

  • 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.

  • Located in the centre of Chicago, 2.4 km from Ohio Street Beach and less than 1 km from Willis Tower, Loop 2BR w Pool Gym nr Financial District L CHI-247 offers free WiFi, a shared lounge and air...

  • Set in the centre of Chicago, 2.4 km from Ohio Street Beach and less than 1 km from Willis Tower, Loop Studio w gym pool lounge 1 block from L CHI-694 offers free WiFi, an indoor pool and air...

  • 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.

  • 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.

Highly rated holiday rentals in Chicago and nearby

  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 165 reviews

    Set in Chicago, 4.4 km from United Center and 7.1 km from Union Station, Perfect place to enjoy the city or just relax offers accommodation with free WiFi in a historic building.

    From US$177.94 per night
  • 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.

  • 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 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