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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2F Chicago's Little Italy near West Loop & Downtown
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.
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.
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...
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...
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.
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 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.
Level Chicago River North
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...
Highly rated holiday rentals in Chicago and nearby
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.
Lincoln Park 3 BR Penthouse
Located within the Lincoln Park district in Chicago, Lincoln Park 3 BR Penthouse has air conditioning, a balcony, and city views.
Perfect place to enjoy the city or just relax
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.
Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans!
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.
Hyde Park Modern Private Room - Near Univ of Chicago
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.
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.
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.
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 The Plymouth Apartments Loop
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.
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 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.
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 gym playroom pool close to L CHI-960
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...
Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382
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...
Enjoy breakfast in Chicago and nearby
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.
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.
River N 2BR w Gym WD nr Magnificent Mile CHI-164
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.
River N 2BR w Gym WD nr Magnificent Mile CHI-160
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.
River N 2BR wGym Deck Pool nr Mag Mile CHI-133
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.
