Holiday Rentals in Chicago
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The best 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
Scored out of 10, guest rating 9.1Superb - What previous guests thought, 211 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.1Very good - What previous guests thought, 361 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 9.3Superb - What previous guests thought, 312 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.0Very good - What previous guests thought, 156 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 7.4Good - What previous guests thought, 298 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.0Very good - What previous guests thought, 382 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.2Very good - What previous guests thought, 513 reviewsPopular with guests booking holiday rentals in Chicago
Popular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.7Fabulous - What previous guests thought, 325 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 2,044 reviews
Highly rated holiday rentals in Chicago and nearby
- Scored out of 10, guest rating 8.2Very good - What previous guests thought, 513 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.
Wicker Park Inn
Wicker Park, Chicago8.0+ review scoreScored out of 10, guest rating 8.9Fabulous - What previous guests thought, 43 reviewsFeaturing garden views, Wicker Park Inn offers accommodation with patio, around 3.6 km from United Center. The 3-star bed and breakfast has air-conditioned rooms with a private bathroom and free WiFi.
From US$331.22 per nightPerfect place to enjoy the city or just relax
Chicago8.0+ review scoreScored out of 10, guest rating 8.5Very good - What previous guests thought, 163 reviewsSet 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.
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Chicago Loop, Chicago8.0+ review scoreScored out of 10, guest rating 8.6Fabulous - What previous guests thought, 51 reviewsExperience 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...
The Penthouse at Grand Plaza
River North, Chicago8.0+ review scoreScored out of 10, guest rating 9.3Superb - What previous guests thought, 101 reviewsLocated 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.
Kasa South Loop Chicago
South Loop, Chicago8.0+ review scoreScored out of 10, guest rating 8.7Fabulous - What previous guests thought, 325 reviewsFeaturing 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
River North, Chicago8.0+ review scoreScored out of 10, guest rating 9.1Superb - What previous guests thought, 39 reviewsSituated 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
Chicago8.0+ review scoreScored out of 10, guest rating 8.7Fabulous - What previous guests thought, 46 reviewsAurelien 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.
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, Loop 1BR w Gym Pool WD nr Millennium Park CHI-236 provides 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.
Loop 1BR w gym doorman same block as L CHI-672
Chicago Loop, ChicagoBreakfast optionsSituated 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
Chicago Loop, ChicagoBreakfast optionsSituated 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.
Loop 1BR w Pool Gym nr Theatre District CHI-277
Chicago Loop, ChicagoBreakfast optionsSituated 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.
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...
Loop 1BR w Pool Gym nr the L Riverwalk CHI-242
Chicago Loop, ChicagoBreakfast optionsLocated 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.
These holiday rentals in Chicago and nearby have options with free cancellation
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Chicago Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.6Good - What previous guests thought, 467 reviewsSonder 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$264.99 per nightSonder by Marriott Bonvoy The Plymouth Apartments Loop
Chicago Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.6Good - What previous guests thought, 363 reviewsSituated 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
West Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.7Good - What previous guests thought, 145 reviewsIn 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
West Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.4Good - What previous guests thought, 298 reviewsLocated 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 gym pool lounge 1 block from L CHI-700
Chicago Loop, ChicagoFree cancellation options availableSet right in the centre of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w gym pool lounge 1 block from L CHI-700 offers air-conditioned accommodation with free WiFi and a TV.
Loop Studio w gym pool lounge 1 block from L CHI-694
Chicago Loop, ChicagoFree cancellation options availableSet 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...
Loop 1BR w Gym Pool WD nr Financial District CHI-229
Chicago Loop, ChicagoFree cancellation options availableLocated in the centre of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Gym Pool WD nr Financial District CHI-229 provides air-conditioned accommodation with free WiFi and a TV.
Loop 1BR w Gym Pool WD nr Financial District CHI-222
Chicago Loop, ChicagoFree cancellation options availableSet 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...
FAQ about holiday rentals in Chicago
Holiday rentals that guests love in Chicago
- Avg. price/night: US$317.73Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 31 reviewsRosa & 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 byNosalYoung couple
- Scored out of 10, guest rating 7.4Good - What previous guests thought, 298 reviewsLooks like a vacation houseGuest review byLinhYoung couple
- Avg. price/night: US$317.73Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 31 reviewsThe 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 bySydneyGroup
