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.

T
Tony
From
Italy
Central to where wanted to visit. Large property that was very comfortable.
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.

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, 184 reviews
Price from
US$199.19
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
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, 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.

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, 2,041 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.

L
Li
From
United Kingdom
Well equipped, comfortable and stylish apartment, which was perfect as a chance to recharge and catch up on laundry after a week of staying in hotels on a business trip. Right next to an amazing breakfast restaurant that's a Chicago institution, and within walking distance of lots of interesting places including Symphony Hall and theatre district. Sonder app is well worth downloading as it gives lots of functionality, including early check-in (for a fee),, virtual fee and other information about your booking. Extremely good value when I stayed.
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.

G
Grainne
From
Ireland
Absolutely fantastic property. Perfect location for walking around the city. So clean. Plenty of fresh towels, kitchen towels, even salt and pepper etc and facilities for washing clothes including detergent! Check in was contactless and there are even lockers to store your luggage after check out.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 339 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$206.40
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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Holiday Rentals with swimming pools in Chicago and nearby

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, 363 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$410.37 per night
  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 145 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$194.39 per night

  • Set in Chicago, less than 1 km from Shops at Northbridge and a 11-minute walk from Chicago Museum of Contemporary Art, Streeterville 1BR w Gym Pool nr Navy Pier CHI-412 provides accommodation with...

  • 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.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 339 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

  • Kasa South Loop Chicago

    South Loop, Chicago
    Free cancellation options available
    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.

  • 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...

  • Located in the centre of Chicago, 1.4 km from Oak Street Beach, River N 2BR w Gym WD nr Magnificent Mile CHI-164 provides air-conditioned accommodation with free WiFi and a TV.

Highly rated holiday rentals in Chicago and nearby

  • 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 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.

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 19 reviews

    Set within 1.3 km of Union Station and 1.7 km of Willis Tower, Sage Modern Apartments Near Union Park in West Loop offers rooms with air conditioning and a private bathroom in Chicago.

  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 10 reviews

    Avenir West Loop Penthouses with Iconic City Views is situated in the West Town district in Chicago, and has a rooftop pool, a kitchen and city views.

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
    Avg. price/night: US$132.68
    Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 299 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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