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 9.4
Superb - What previous guests thought, 131 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.

J
Jessika
From
Italy
Incredible staff first and foremost who made my stay welcoming from the beginning. There was community space and yet complete privacy and autonomy. There were tiny touches all around, such as a selection of curated treats up front, bottled water as you needed, and a back porch that offered beautiful mornings with coffee. Enjoyed most the good feelings of walking in and coming to my room. I want to visit Chicago again simply to bring my daughter to this location- thank you all again.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 184 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
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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 9.2
Superb - What previous guests thought, 47 reviews
Price from
US$285
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, 31 reviews
Price from
US$205.85
1 night, 2 adults
Check availability

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.

K
Katharina
From
Germany
Amazing Apartment Hotel. Loved everything. Especially the pool area and the gym. Enjoyed having a small kitchen. It was stocked with everything you need. The staff is super nice and helpful. Would 100% recommend staying here.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,043 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.

H
Hilda
From
New Zealand
Loved the location, right by Union. Easy to walk to city or uber back from games ice hockey a lotd basketball
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 362 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.

K
Keziah
From
New Zealand
Beautiful, very comfortable apartment with everything we needed. Fantastic location.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 341 reviews
Price from
US$216.75
1 night, 2 adults
Check availability

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, 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$203.82
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 8.6
    Fabulous - What previous guests thought, 52 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, 341 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$204.67 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 326 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, 39 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, 46 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 8.2
    Very good - What previous guests thought, 510 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.

Holiday Rentals with swimming pools in Chicago and nearby

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

Enjoy breakfast in Chicago and nearby

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

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  • 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, 31 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 7.4
    Good - What previous guests thought, 300 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, 31 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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