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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.

L
Lechosław
From
Poland
The apartment was wonderful, exceeded our expectations. Unlike others, it felt like living in your own apartment, not a place to rent. John was a very nice host. The apartment is located in a quiet area, five minutes walk to the subway, very well equipped.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 184 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.

H
Hatem
From
France
Many thanks to the owners for their kindness and help during our stay. The apartment is very large, we were eight and did not lack space. All the rooms are very well appointed and the kitchen is spacious. The area is peaceful and only 30 minutes from the city center. Public transport (bus, metro) is easily accessible. We can only recommend this apartment and thank the owners again for all their help.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 131 reviews
Price from
US$136.12
1 night, 2 adults

Forrestville Ave Large Suite

Bronzeville, Chicago

Located in Chicago, 2.3 km from Oakwood Beach and 3.8 km from Guaranteed Rate Field, Forrestville Ave Large Suite provides accommodation with free WiFi in a historic building.

L
Laura
From
United Kingdom
Fantastic hosts - respond quickly to messages and were excellent meeting us on arrival and showing us around the property. Good space and spotlessly clean. Good neighbourhood about 20 mins drive from the centre of Chicago and on street parking was easy.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 107 reviews
Price from
US$126
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.

S
Susie Katja
From
Denmark
amazing breakfast amazing staff
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 178 reviews
Price from
US$199.19
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.

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 9.4
Superb - What previous guests thought, 29 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.

S
Søren
From
Denmark
Friendly staff, homey atmosphere, amazing breakfast. Would stay here again!
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.

j
janice
From
United Kingdom
Beautiful villa with homely feel . Absolute gorgeous breakfast all home made in the morning as well as cereal , fruit etc Bedroom was excellent with everything you need such as extra towels , dressing gowns and slippers for the Hot Tub .
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
Martina
From
United States
The studio is wonderful, usually quiet (probably I was also kinda lucky with the neighbors), has a kitchen with a proper gas stove, a queen size bed, new appliances, and a bathroom with a huge shower. The gym has proper weightlifting equipment, including a barbell.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,031 reviews
Price from
US$169
1 night, 2 adults

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.

D
David
From
El Salvador
The space, the design, the cleaning, the location.
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 385 reviews
Price from
US$218.45
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 7.4
Good - What previous guests thought, 305 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 395 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 318 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 8.2
Very good - What previous guests thought, 385 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 212 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 328 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 411 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 505 reviews

Popular with guests booking holiday rentals in Chicago

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 2,031 reviews

Enjoy breakfast in Chicago and nearby

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...

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 57 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.

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...

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.

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...

Holiday Rentals with swimming pools in Chicago and nearby

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.

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 9.1
Superb - What previous guests thought, 46 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 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.

Situated right in the centre of Chicago, 700 metres from Field Museum Of Natural History, S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740 features air-conditioned accommodation with free WiFi and a TV...

Set in the heart of Chicago, 700 metres from Field Museum Of Natural History, S Loop 1BR w Pool Gym Spa nr Grant Park CHI-741 offers air-conditioned accommodation with free WiFi and a TV.

Highly rated holiday rentals in Chicago and nearby

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 505 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$301.29 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 55 reviews

Located within the Lincoln Park district in Chicago, Lincoln Park 3 BR Penthouse has air conditioning, a balcony, and city views.

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 163 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.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 34 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 8.6
Fabulous - What previous guests thought, 350 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$142.96 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 328 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 8.8
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...

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, 471 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...

From US$142.96 per night
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 367 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$132.68 per night
Scored out of 10, guest rating 7.8
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 7.4
Good - What previous guests thought, 305 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$122.39 per night

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.

Situated right in the heart of Chicago, 300 metres from Willis Tower, Loop 1BR w Gym Roofdeck WD nr W Loop the CHI-210 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...

Located in a central area of Chicago, 2.9 km from Oak Street Beach, River North 1br w gym pool roof nr Riverwalk CHI-816 provides air-conditioned accommodation with free WiFi and a TV.

FAQ about holiday rentals in Chicago

Holiday rentals that guests love in Chicago

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Avg. price/night: US$91
Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 220 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, 33 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
Avg. price/night: US$317.73
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
Avg. price/night: US$122.39
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 305 reviews
Looks like a vacation house
Guest review by
Linh
Young couple
Avg. price/night: US$317.73
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