Holiday Rentals in Chicago
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Holiday Rentals for every style
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The best 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.
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.
Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub
A recently renovated holiday home situated in Chicago, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub features a garden.
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.
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.
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.
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.
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.
Highly rated holiday rentals in Chicago and nearby
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.
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.
These holiday rentals in Chicago and nearby have options with free cancellation
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 Gym Pool WD nr Millennium Park CHI-226
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.
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...
Loop 1BR w Gym Roof Lounge same block as L CHI-670
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.
Streeterville 1BR w Gym Pool nr Navy Pier CHI-412
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...
River North 1br w gym pool roof nr Riverwalk CHI-821
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.
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...
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.
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.
River N 1BR w Gym Rooftop 1 block to L CHI-398
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.
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.
