Holiday Rentals in Chicago
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Holiday Rentals for every style
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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
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.
Forrestville Ave Large Suite
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.
Ray's Bucktown Bed and Breakfast
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.
Designer Themed 4 Bedroom in Best Location with Patio and Fireplace
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.
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
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...
The Polo Inn Bridgeport U.S.A.
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.
Villa D' Citta
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.
Sentral Michigan Avenue
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.
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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.
Sonder by Marriott Bonvoy The Opal Apartments River North
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.
Most booked holiday rentals in Chicago and surroundings in the past month
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Holiday Rentals with swimming pools in Chicago and nearby
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
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...
Situated right in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w gym pool lounge 1 block from L CHI-695 features air-conditioned accommodation with free WiFi and a TV.
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 Theatre District CHI-277 features 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 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...
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 Studio w gym pool lounge 1 block from L CHI-694 offers free WiFi, an indoor pool and air...
These holiday rentals in Chicago and nearby have options with free cancellation
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
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...
Sonder by Marriott Bonvoy Greektown Apartments
In the West Loop district of Chicago, close to Union Station, Sonder by Marriott Bonvoy Greektown Apartments has free WiFi and a washing machine.
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
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.
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
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.
Lincoln Park Apartment with Backyard!
Situated in Chicago, 2.1 km from Fullerton Beach and 1.8 km from Lincoln Park Zoo, Lincoln Park Apartment with Backyard! features air-conditioned accommodation with a patio and free WiFi.
5430 Happy Home
Set within 4.5 km of Museum of Science and Industry - Chicago and 4.8 km of Guaranteed Rate Field in Chicago, 5430 Happy Home offers accommodation with free WiFi and seating area.
Loop 1BR w Lounge Rooftop nr Art Institute CHI-103
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.
Loop 2br w lounge gym nr Chicago Riverwalk CHI-959
Located in the centre of Chicago, 1.7 km from Ohio Street Beach and 300 metres from Millennium Station, Loop 2br w lounge gym nr Chicago Riverwalk CHI-959 offers free WiFi, a shared lounge and air...
Enjoy breakfast in Chicago and nearby
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.
Loop 1BR w gym doorman same block as L CHI-672
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...
Loop 2BR w Gym Doorman same block as L CHI-674
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.
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.
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...
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.
The Penthouse at Grand Plaza
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 Chicago, less than 1 km from Shops at Northbridge and a 11-minute walk from Chicago Museum of Contemporary Art, Streeterville Studio w pool gym nr Navy Pier CHI-786 provides accommodation with...
Highly rated holiday rentals in Chicago and nearby
Kasa South Loop Chicago
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.
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
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.
Aurelien Spacious Apartments in the Heart of Gold Coast
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.
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...
Historic luxury Townhouse in Downtown Chicago
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...
Studio flat in the heart of Downtown Chicago
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.
Right in the heart of Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests has garden views from the balcony.
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.
