Holiday Rentals in Chicago
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Holiday Rentals for every style
Find the right holiday rental for you in Chicago
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.
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.
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.
1F Cozy Home in Little Italy near Downtown West Loop United Center
Offering city views, 1F Cozy Home in Little Italy near Downtown West Loop United Center is an accommodation set in Chicago, 3.9 km from Union Station and 4.1 km from Depaul University.
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.
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
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.
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.
Set in the heart of Chicago, 1.7 km from Ohio Street Beach, Loop Studio w Gym Pool nr Chicago Riverwalk CHI-240 offers air-conditioned accommodation with free WiFi and a TV.
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...
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.
Set in the heart of Chicago, 2.4 km from Ohio Street Beach, Loop 1BR w Pool Gym nr Financial District CHI-282 offers air-conditioned accommodation with free WiFi and a TV.
Loop 1BR w Pool Gym nr the L Riverwalk CHI-242
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...
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.
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...
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.
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.
Set right in the centre of Chicago, 700 metres from Field Museum Of Natural History, S Loop 1BR w Pool Gym nr Soldier Field CHI-350 offers air-conditioned accommodation with free WiFi and a TV.
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...
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.
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.
Avenir West Loop Penthouses with Iconic City Views
Avenir West Loop Penthouses with Iconic City Views is situated in the West Town district in Chicago, and has a rooftop pool, a kitchen and city views.
These holiday rentals in Chicago and nearby have options with free cancellation
Loop 1BR w Fitness center nr W Loop the L CHI-194
Located in the centre of Chicago, 300 metres from Willis Tower, Loop 1BR w Fitness center nr W Loop the L CHI-194 provides 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 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.
River North 1br w gym lounge roof nr Riverwalk CHI-900
Set right in the centre of Chicago, 1.7 km from Oak Street Beach, River North 1br w gym lounge roof nr Riverwalk CHI-900 offers air-conditioned accommodation with free WiFi and a TV.
River North 1br w gym lounge roof nr Riverwalk CHI-893
Situated right in the heart of Chicago, 1.7 km from Oak Street Beach, River North 1br w gym lounge roof nr Riverwalk CHI-893 features air-conditioned accommodation with free WiFi and a TV.
River North 1br w gym lounge roof nr Riverwalk CHI-895
Situated right in the heart of Chicago, 1.7 km from Oak Street Beach, River North 1br w gym lounge roof nr Riverwalk CHI-895 features air-conditioned accommodation with free WiFi and a TV.
