Vacation Rentals in Chicago
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The best vacation rentals in Chicago
Check out our selection of great vacation rentals in Chicago
- Scored out of 10, guest rating 9.4Wonderful - What previous guests thought, 133 reviewsFrom$1361 night, 2 adults
- Scored out of 10, guest rating 9.4Wonderful - What previous guests thought, 188 reviewsFrom$1991 night, 2 adults
- Scored out of 10, guest rating 9.3Wonderful - What previous guests thought, 29 reviewsFrom$4191 night, 2 adults
- Scored out of 10, guest rating 9.6Exceptional - What previous guests thought, 5 reviewsFrom$4991 night, 2 adults
- Scored out of 10, guest rating 9.1Wonderful - What previous guests thought, 48 reviewsFrom$2701 night, 2 adults
- Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 32 reviewsFrom$2061 night, 2 adults
- Scored out of 10, guest rating 8.8Excellent - What previous guests thought, 2,045 reviewsFrom$1691 night, 2 adults
- Scored out of 10, guest rating 8.1Very Good - What previous guests thought, 351 reviewsFrom$2371 night, 2 adults
- Scored out of 10, guest rating 8.6Excellent - What previous guests thought, 335 reviewsFrom$3401 night, 2 adults
- Scored out of 10, guest rating 8.6Excellent - What previous guests thought, 330 reviewsFrom$2121 night, 2 adults
- Scored out of 10, guest rating 8.0Very Good - What previous guests thought, 386 reviewsFrom$881 night, 2 adults
- Scored out of 10, guest rating 8.2Very Good - What previous guests thought, 525 reviewsFrom$1891 night, 2 adults
- Scored out of 10, guest rating 8.7Excellent - What previous guests thought, 322 reviewsFrom$5101 night, 2 adults
- Scored out of 10, guest rating 8.9Excellent - What previous guests thought, 105 reviewsFrom$1261 night, 2 adults
- Scored out of 10, guest rating 8.6Excellent - What previous guests thought, 27 reviewsFrom$1601 night, 2 adults
- Scored out of 10, guest rating 7.5Good - What previous guests thought, 292 reviewsFrom$2251 night, 2 adults
- Scored out of 10, guest rating 7.6Good - What previous guests thought, 467 reviewsFrom$2141 night, 2 adults
- Scored out of 10, guest rating 7.7Good - What previous guests thought, 147 reviewsFrom$2731 night, 2 adults
- Scored out of 10, guest rating 6.6Pleasant - What previous guests thought, 218 reviewsFrom$1061 night, 2 adults
- Scored out of 10, guest rating 7.6Good - What previous guests thought, 366 reviewsFrom$2211 night, 2 adults
Most booked vacation rentals in Chicago and surrounding area in the past month
Popular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 9.3Wonderful - What previous guests thought, 317 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 5.7Fair - What previous guests thought, 419 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 7.8Good - What previous guests thought, 145 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 9.1Wonderful - What previous guests thought, 206 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.1Very Good - What previous guests thought, 351 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 7.5Good - What previous guests thought, 292 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.7Excellent - What previous guests thought, 322 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.2Very Good - What previous guests thought, 525 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.0Very Good - What previous guests thought, 386 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 8.8Excellent - What previous guests thought, 2,045 reviews
Highly rated vacation rentals in Chicago and nearby
Wicker Park Inn
Wicker Park, Chicago8.0+ review scoreScored out of 10, guest rating 8.9Excellent - What previous guests thought, 45 reviewsWicker Park Inn enjoys a location in Chicago, 2.3 miles from United Center and 2.8 miles from Water Tower Chicago.
From $331.22 per nightExperience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Chicago Loop, Chicago8.0+ review scoreScored out of 10, guest rating 8.6Excellent - What previous guests thought, 48 reviewsExperience Downtown Chicago at Millennium - Luxury Apartments in The Loop features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster,...
The Penthouse at Grand Plaza
River North, Chicago8.0+ review scoreScored out of 10, guest rating 9.3Wonderful - What previous guests thought, 100 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 8.7Excellent - What previous guests thought, 322 reviewsJust a 18-minute walk from Art Institute of Chicago and 0.9 miles from Chicago Symphony Orchestra, Kasa South Loop Chicago features accommodations in Chicago, with a shared lounge.
- Scored out of 10, guest rating 8.1Very Good - What previous guests thought, 351 reviews
Sonder by Marriott Bonvoy The Burnham Apartments Loop offers accommodations within one mile of the center 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 9.1Wonderful - What previous guests thought, 35 reviewsThe Bernardin Gold Coast Luxury Apartments Near Magnificent Mile is an apartment featuring rooms with free Wifi and air conditioning in the center of Chicago.
Aurelien Spacious Apartments in the Heart of Gold Coast
Chicago8.0+ review scoreScored out of 10, guest rating 8.7Excellent - What previous guests thought, 45 reviewsAurelien Spacious Apartments in the Heart of Gold Coast provides accommodations within 0.7 miles of the center of Chicago, with free Wifi and a kitchen with a microwave, a toaster, and a fridge.
- Scored out of 10, guest rating 9.3Wonderful - What previous guests thought, 17 reviews
Just a 19-minute walk from Union Station and 1.2 miles from Willis Tower, K2 Sky High Apartments with Stunning Chicago Views in West Loop features accommodations in Chicago, with a shared lounge.
Enjoy breakfast in Chicago and nearby
Loop 1BR w Lounge Rooftop nr Art Institute CHI-103 offers accommodations in Chicago, a 1-minute walk from Chicago Symphony Orchestra and half a mile from Willis Tower.
Loop 1BR w WD Gym Rooftop Pool 2 blocks to L CHI-382 offers accommodations in Chicago, a 11-minute walk from Cloud Gate – The Bean and half a mile from Chicago Symphony Orchestra.
Loop 2BR w Gym Doorman same block as L CHI-674
Chicago Loop, ChicagoBreakfast optionsLoop 2BR w Gym Doorman same block as L CHI-674 is located in Chicago, just a 7-minute walk from Chicago Symphony Orchestra and 0.4 miles from Willis Tower.
Just a 11-minute walk from Willis Tower and 0.6 miles from CIBC Theatre, Loop 2BR w Pool Gym nr Financial District L CHI-247 features accommodations in Chicago with a shared lounge.
Loop Studio w gym pool lounge 1 block from L CHI-694 features accommodations in the center of Chicago, 1.5 miles from Ohio Street Beach and a 11-minute walk from Willis Tower.
Just a 15-minute walk from Millennium Park and 0.9 miles from DePaul University, Loop 1BR w Gym Pool WD nr Financial District CHI-222 features accommodations in Chicago with a shared lounge.
Loop 1BR w Fitness center nr W Loop the L CHI-194 offers accommodations in Chicago, a 15-minute walk from Grant Park and 0.7 miles from Art Institute of Chicago.
Streeterville 1BR w Pool Deck nr Beach Park CHI-585 offers accommodations in the center of Chicago, a 4-minute walk from Ohio Street Beach and half a mile from Shops at Northbridge.
These vacation 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 accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, a microwave, and a...
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, 366 reviewsLocated in Chicago, within 1.4 mi of Ohio Street Beach and 1969 feet of Chicago Board of Trade Building, The Plymouth, Sonder Apartments by Marriott Bonvoy features free WiFi.
From $256.10 per nightSonder by Marriott Bonvoy Greektown Apartments
West Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.7Good - What previous guests thought, 147 reviewsSonder by Marriott Bonvoy Greektown Apartments enjoys a location in Chicago, 1.3 miles from Art Institute of Chicago and one mile from DePaul University. This 4-star condo hotel offers free Wifi.
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
West Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.5Good - What previous guests thought, 292 reviewsSonder by Marriott Bonvoy Market Hall Apartments West Loop offers accommodations in Chicago, a 13-minute walk from United Center and 1.7 miles from Union Station.
Streeterville 2BR w Deck Gym nr Beach Park CHI-589
Streeterville, ChicagoFree cancellation options availableStreeterville 2BR w Deck Gym nr Beach Park CHI-589 is located in Chicago, just a 13-minute walk from Water Tower Chicago and 0.8 miles from 360 Chicago.
Level Chicago River North
River North, ChicagoFree cancellation options availableScored out of 10, guest rating 9.0Wonderful - What previous guests thought, 1 reviewLocated in Chicago and with Oak Street Beach reachable within 1.5 miles, Level Chicago River North provides a seasonal outdoor swimming pool, non-smoking rooms, free WiFi throughout the property and a...
Jeffjack Heated Pool Penthouse in Chicago's West Loop
West Loop, ChicagoFree cancellation options availableScored out of 10, guest rating 7.0Good - What previous guests thought, 4 reviewsA 3-minute walk from Union Station in the center of Chicago, Jeffjack Heated Pool Penthouse in Chicago's West Loop provides accommodations with access to a hot tub, fitness room, and indoor pool.
W Loop 1BR w Deck Pool Gym 3 blocks to L CHI-646
West Loop, ChicagoFree cancellation options availableW Loop 1BR w Deck Pool Gym 3 blocks to L CHI-646 is located in Chicago, just 1.1 miles from Millennium Station and 1.3 miles from DePaul University.
FAQ about vacation rentals in Chicago
Vacation Rentals That Guests Love in Chicago
- Avg. price/night: $231.67Scored out of 10, guest rating 6.6Pleasant - What previous guests thought, 218 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: $345.48Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 32 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 7.5Good - What previous guests thought, 292 reviewsLooks like a vacation houseGuest review byLinhYoung couple
- Avg. price/night: $345.48Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 32 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
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