Vacation Rentals in Chicago
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The best vacation rentals in Chicago
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The Avondale Guesthouse
The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.
Ray's Bucktown Bed and Breakfast
Ray's Bucktown Bed and Breakfast provides a sauna and free private parking, and is within 3.1 miles of Lincoln Park Zoo and 3.2 miles of Wrigley Field.
Designer Themed 4 Bedroom in Best Location with Patio and Fireplace
Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.
The Polo Inn Bridgeport U.S.A.
Offering air-conditioned rooms in the Bridgeport district of Chicago, The Polo Inn Bridgeport U.S.A. Is 1.1 miles from Guaranteed Rate Field.
Villa D' Citta
Villa D' Citta enjoys a location in Chicago, 1.4 miles from North Avenue Beach and a 18-minute walk from Lincoln Park Zoo.
Sentral Michigan Avenue
Sentral Michigan Avenue offers accommodations within 1.1 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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.
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North features accommodations within 0.4 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.
Cubs! Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans!
Cubs! Prime Location! - 1 Min Walk to Wrigley Field - 2BR Apts Perfect for Cubs Fans! offers accommodations in Chicago, a 3-minute walk from Wrigley Field and 2.4 miles from Lincoln Park Zoo.
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 9.1Wonderful - What previous guests thought, 206 reviewsPopular with guests booking vacation rentals in Chicago
Scored out of 10, guest rating 7.8Good - What previous guests thought, 147 reviewsPopular 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 8.1Very Good - What previous guests thought, 352 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 5.6Fair - What previous guests thought, 420 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 8.2Very Good - What previous guests thought, 525 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 8.8Excellent - What previous guests thought, 2,050 reviews
Enjoy breakfast in Chicago and nearby
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Chicago Loop, ChicagoBreakfast optionsScored out of 10, guest rating 7.6Good - What previous guests thought, 466 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...
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.
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop
Chicago Loop, ChicagoBreakfast optionsScored out of 10, guest rating 8.6Excellent - What previous guests thought, 49 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,...
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.
- Scored out of 10, guest rating 7.6Good - What previous guests thought, 366 reviews
Located 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 night 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.
These vacation rentals in Chicago and nearby have options with free cancellation
Loop 1BR w Gym Pool WD nr Financial District CHI-222
Chicago Loop, ChicagoFree cancellation options availableJust 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
Chicago Loop, ChicagoFree cancellation options availableLoop 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.
The Penthouse at Grand Plaza
River North, ChicagoFree cancellation options availableScored 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.
Streeterville 1BR w Pool Deck nr Beach Park CHI-585
Streeterville, ChicagoFree cancellation options availableStreeterville 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.
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.
Sonder by Marriott Bonvoy The Opal Apartments River North
River North, ChicagoFree cancellation options availableScored out of 10, guest rating 8.6Excellent - What previous guests thought, 335 reviewsSonder by Marriott Bonvoy The Opal Apartments River North features accommodations within 0.4 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.
Kasa South Loop Chicago
South Loop, ChicagoFree cancellation options availableScored 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.
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...
Highly rated vacation rentals in Chicago and nearby
- Scored out of 10, guest rating 8.1Very Good - What previous guests thought, 352 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.
- Scored out of 10, guest rating 8.2Very Good - What previous guests thought, 525 reviews
Sonder by Marriott Bonvoy South Wabash Apartments South Loop offers accommodations in Chicago, 1.2 miles from Art Institute of Chicago and 1.2 miles from Chicago Symphony Orchestra.
From $349.69 per night Historic luxury Townhouse in Downtown Chicago
Chicago8.0+ review scoreScored out of 10, guest rating 9.8Exceptional - What previous guests thought, 7 reviewsHistoric luxury Townhouse in Downtown Chicago is located in Chicago, just a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.
Studio flat in the heart of Downtown Chicago
Chicago8.0+ review scoreScored out of 10, guest rating 8.6Excellent - What previous guests thought, 20 reviewsStudio flat in the heart of Downtown Chicago offers accommodations in Chicago, a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.
- Scored out of 10, guest rating 8.8Excellent - What previous guests thought, 5 reviews
Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests features accommodations in Chicago with a garden.
FAQ about vacation rentals in Chicago
Vacation Rentals That Guests Love in Chicago
- Avg. price/night: $231.67Scored out of 10, guest rating 6.7Pleasant - What previous guests thought, 219 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
