Holiday Rentals in Chicago
Find the holiday rentals that appeal to you the most
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
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 176 reviewsFromUS$2251 night, 2 adults
- Scored out of 10, guest rating 9.3Superb - What previous guests thought, 317 reviewsFromUS$2891 night, 2 adults
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 187 reviewsFromUS$1921 night, 2 adults
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 8 reviewsFromUS$4501 night, 2 adults
- Scored out of 10, guest rating 9.3Superb - What previous guests thought, 29 reviewsFromUS$4191 night, 2 adults
- Scored out of 10, guest rating 9.6Exceptional - What previous guests thought, 5 reviewsFromUS$4991 night, 2 adults
- Scored out of 10, guest rating 9.1Superb - What previous guests thought, 48 reviewsFromUS$2701 night, 2 adults
- Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 33 reviewsFromUS$2061 night, 2 adults
- Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 2,048 reviewsFromUS$1691 night, 2 adults
- Scored out of 10, guest rating 8.1Very good - What previous guests thought, 346 reviewsFromUS$2461 night, 2 adults
- Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 331 reviewsFromUS$4541 night, 2 adults
- Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 327 reviewsFromUS$2121 night, 2 adults
- Scored out of 10, guest rating 8.0Very good - What previous guests thought, 384 reviewsFromUS$881 night, 2 adults
- Scored out of 10, guest rating 8.2Very good - What previous guests thought, 525 reviewsFromUS$1891 night, 2 adults
- Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 320 reviewsFromUS$5101 night, 2 adults
- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 106 reviewsFromUS$1261 night, 2 adults
- Scored out of 10, guest rating 8.3Very good - What previous guests thought, 46 reviewsFromUS$1801 night, 2 adults
- Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 27 reviewsFromUS$1711 night, 2 adults
- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 45 reviewsFromUS$2821 night, 2 adults
- Scored out of 10, guest rating 7.6Good - What previous guests thought, 289 reviewsFromUS$1791 night, 2 adults
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 9.3Superb - What previous guests thought, 317 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 7.7Good - What previous guests thought, 143 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 5.7Passable - What previous guests thought, 419 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 9.1Superb - What previous guests thought, 204 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.1Very good - What previous guests thought, 346 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 7.6Good - What previous guests thought, 289 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 320 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.2Very good - What previous guests thought, 525 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.0Very good - What previous guests thought, 384 reviewsPopular with guests booking holiday rentals in Chicago
Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 2,048 reviews
Highly rated holiday rentals in Chicago and nearby
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, 46 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.
- Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 331 reviews
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.
Kasa South Loop Chicago
South Loop, Chicago8.0+ review scoreScored out of 10, guest rating 8.6Fabulous - What previous guests thought, 320 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.
- Scored out of 10, guest rating 8.1Very good - What previous guests thought, 346 reviews
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.
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
River North, Chicago8.0+ review scoreScored out of 10, guest rating 9.3Superb - What previous guests thought, 32 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, 45 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.
- Scored out of 10, guest rating 9.3Superb - What previous guests thought, 17 reviews
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...
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...
Loop 1BR w Lounge Rooftop nr Art Institute CHI-103
Chicago Loop, ChicagoFree cancellation options availableLocated 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 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382
Chicago Loop, ChicagoFree cancellation options availableLocated 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 2BR w Gym Doorman same block as L CHI-674
Chicago Loop, ChicagoFree cancellation options availableSituated 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.
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Chicago Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.6Good - What previous guests thought, 367 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.
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-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...
Loop 1BR w Fitness center nr W Loop the L CHI-194
Chicago Loop, ChicagoFree cancellation options availableLocated 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.
Enjoy breakfast in Chicago and nearby
Situated right in the centre of Chicago, 300 metres from Ohio Street Beach, Streeterville 1BR w Pool Deck nr Beach Park CHI-585 features air-conditioned accommodation with free WiFi and a TV.
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
River North, ChicagoBreakfast optionsScored out of 10, guest rating 9.0Superb - What previous guests thought, 1 reviewSet 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...
- Scored out of 10, guest rating 7.0Good - What previous guests thought, 4 reviews
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.
W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-646
West Loop, ChicagoBreakfast optionsSituated in Chicago, 1.1 km from Union Station and 1.4 km from Willis Tower, W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-646 offers a rooftop pool and air conditioning.
Situated right in the heart of Chicago, 700 metres from Field Museum Of Natural History, South Loop 1br w pool bbq gym nr Grant Park CHI-776 features air-conditioned accommodation with free WiFi and a...
River N Studio w Gym Pool nr L stop CHI-366
ChicagoBreakfast optionsLocated in a central area of Chicago, 1.3 km from Oak Street Beach, River N Studio w Gym Pool nr L stop CHI-366 provides air-conditioned accommodation with free WiFi and a TV.
Offering city views, Gold Coast 2BR w Gym Roof nr Water Tower CHI-389 is an accommodation situated in Chicago, 300 metres from 360 Chicago and 500 metres from Water Tower Chicago.
FAQ about holiday rentals in Chicago
Holiday rentals that guests love in Chicago
- Avg. price/night: US$231.67Scored out of 10, guest rating 6.5Pleasant - What previous guests thought, 216 reviewsIm so happy i came across Villa Dubois Guesthouse. The whole property is clean and organized, free street parking, neighborhood is quiet. I love the full functional kitchen where you can prepare meals.security cameras around the common area for safety.If you dont mind sharing a space with strangers,this a nice budget friendly place to stay😊Guest review byLIW-LIWAYoung couple
- Avg. price/night: US$317.73Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 33 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 7.6Good - What previous guests thought, 289 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, 33 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
