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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.

E
Ellen Requena
From
United States
Close to the subway, well-equipped kitchen, beautiful and safe neighborhood, free parking on the street.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 189 reviews
Price from
US$180
1 night, 2 adults

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.

G
Gonzalez
From
Colombia
The location was perfect, it was also very clean and the owner was really very attentive, I would recommend it
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 130 reviews
Price from
US$136.12
1 night, 2 adults

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.

D
David
From
Germany
Very unique place to stay. Staff is super friendly and helpful. this has been one of our best stays ever. Homemade Breakfast is extraordinary good!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 177 reviews
Price from
US$199.19
1 night, 2 adults

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$300
1 night, 2 adults

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.

G
Giovanni
From
Italy
Breakfast was amazing, the 0lace is super and location is great, with free and efficient parking. Great service also
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 30 reviews
Price from
US$419
1 night, 2 adults

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

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.

D
David (Ao)
From
Canada
The breakfast at the Inn was amazing, the owner Dave Samber was very friendly and I had a great stay.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 48 reviews
Price from
US$285
1 night, 2 adults

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 9.6
Exceptional - What previous guests thought, 32 reviews
Price from
US$205.85
1 night, 2 adults

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.

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, 2,025 reviews
Price from
US$169
1 night, 2 adults

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.

K
Kristof
From
Austria
Fab location with close to the station. The host was so helpful and responsive. Highly recommended!
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 331 reviews
Price from
US$201.24
1 night, 2 adults
All holiday rentals in Chicago

Most booked holiday rentals in Chicago and surroundings in the past month

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Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 189 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 166 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 162 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 331 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 317 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 55 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 211 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 409 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 331 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,025 reviews

Holiday Rentals with swimming pools in Chicago and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 59 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...

Set in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr Financial District CHI-281 offers air-conditioned accommodation with free WiFi and a TV.

Situated right in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr Financial District CHI-261 features air-conditioned accommodation with free WiFi and a TV.

Located in a central area of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr the L Riverwalk CHI-242 provides air-conditioned accommodation with free WiFi and a TV.

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, less than 1 km from Ohio Street Beach, Streeterville 1br w pool gym nr Riverwalk CHI-878 provides air-conditioned accommodation with free WiFi and a TV.

Scored out of 10, guest rating 9.4
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.

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.

Highly rated holiday rentals in Chicago and nearby

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 33 reviews

Set in Chicago, 2.3 km from Oakwood Beach and 3.8 km from Museum of Science and Industry - Chicago, Hyde Park Modern Private Room - Near Univ of Chicago offers a garden and air conditioning.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 331 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, 47 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 8.8
Fabulous - What previous guests thought, 53 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 9.2
Superb - What previous guests thought, 18 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, 8 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 8.8
Fabulous - What previous guests thought, 24 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.

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

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.

Located in the centre of Chicago, 1.7 km from Ohio Street Beach and 300 metres from Millennium Station, Loop 2br w gym playroom pool close to L CHI-960 offers free WiFi, a shared lounge and air...

Set in the heart of Chicago, 1.7 km from Ohio Street Beach, Loop 1BR w Gym Pool WD nr Millennium Park CHI-226 offers air-conditioned accommodation with free WiFi and a TV.

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.

Situated in Chicago, 500 metres from CIBC Theatre and 700 metres from Art Institute of Chicago, Loop 1BR w gym doorman same block as L CHI-672 provides accommodation with amenities such as free WiFi...

Situated right in the heart of Chicago, 300 metres from Willis Tower, Loop 1BR w Gym Roof Lounge same block as L CHI-670 features air-conditioned accommodation with free WiFi and a TV.

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, 2.9 km from Oak Street Beach, River North 1br w gym pool roof nr Riverwalk CHI-821 offers air-conditioned accommodation with free WiFi and a TV.

Enjoy breakfast in Chicago and nearby

Located in a central area of Chicago, 1.8 km from Oak Street Beach, River North jr 1br w game room nr beach L CHI-971 provides air-conditioned accommodation with free WiFi and a TV.

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.

Located in a central area of Chicago, 1.4 km from Oak Street Beach, River N 2BR w Gym WD nr Magnificent Mile CHI-160 provides air-conditioned accommodation with free WiFi and a TV.

Situated right in the heart of Chicago, 1.4 km from Oak Street Beach, River N 2BR wGym Deck Pool nr Mag Mile CHI-133 features air-conditioned accommodation with free WiFi and a TV.

Located in the centre of Chicago, 1.7 km from Oak Street Beach, River North 1br w gym lounge roof nr Riverwalk CHI-891 provides air-conditioned accommodation with free WiFi and a TV.

Set in a central area of Chicago, 1.7 km from Oak Street Beach, River N 1BR w Gym Rooftop 1 block to L CHI-398 offers air-conditioned accommodation with free WiFi and a TV.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 7 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.

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

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Avg. price/night: US$93
Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 219 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
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 35 reviews
It's like a little courtyard villa in Montparnasse, with a wrought-iron balcony and birds singing in the garden. Great shower!
Guest review by
Mary
Solo traveller
Scored out of 10, guest rating 9.6
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
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 307 reviews
Looks like a vacation house
Guest review by
Linh
Young couple
Scored out of 10, guest rating 9.6
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