Vacation rentals in Chicago

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Top vacation rentals in Chicago

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.67 mi from city center
$135 nightly
The price is $158 total per night
$158 total
Feb 12 - Feb 13
Total with taxes and fees
This aparthotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A garden, express check-in, and express check-out are also on offer.
Pool
Kitchen
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.59 mi from city center
$160 nightly
The price is $187 total per night
$187 total
Feb 16 - Feb 17
Total with taxes and fees
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Pool
Kitchen
Kasa South Loop Chicago

Kasa South Loop Chicago

4 out of 5
900 S Clark Street Chicago IL
0.7 mi from city center
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This aparthotel features a gym and a rooftop terrace. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a terrace, and express check-out are also offered.
Kitchen
Washer
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
1 mi from city center
$235 nightly
The price is $276 total per night
$276 total
Feb 12 - Feb 13
Total with taxes and fees
A gym, self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. Express check-out is also provided.
Kitchen
Washer
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
1431 W Taylor St Chicago IL
1.96 mi from city center
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This aparthotel features free WiFi in public areas, luggage storage, and laundry facilities. A virtual front desk are provided for your convenience.
Kitchen
Pet friendly
Kasa River North Chicago

Kasa River North Chicago

4 out of 5
808 N Wells St Chicago IL
1.16 mi from city center
$229 nightly
The price is $269 total per night
$269 total
Feb 27 - Feb 28
Total with taxes and fees
This aparthotel features a gym and a seasonal outdoor pool. Business travelers can take advantage of the 24-hour business center. There's a rooftop terrace on site, and concierge services and a virtual front desk are also offered.
Pool
Kitchen
Wrigleyville Suites

Wrigleyville Suites

2 out of 5
3727 N Clifton Ave Chicago IL
5 mi from city center
$132 nightly
The price is $155 total per night
$155 total
Feb 12 - Feb 13
Total with taxes and fees
This aparthotel features free WiFi in public areas, a garden, and laundry facilities. A virtual front desk are provided for your convenience.
Free WiFi
Air conditioning
The Gem Museum Suites

The Gem Museum Suites

3.5 out of 5
1555 Oak Avenue Evanston IL
Free Cancellation
Reserve now, pay when you stay
11.81 mi from city center
$180 nightly
The price is $207 total per night
$207 total
Feb 15 - Feb 16
Total with taxes and fees
This aparthotel features a restaurant, a 24-hour gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like cooked-to-order breakfast and free self parking.
Breakfast included
Kitchen
Urban Farm Fun with Goats 10 Minutes To Downtown!

Urban Farm Fun with Goats 10 Minutes To Downtown!

Chicago IL
4.11 mi from city center
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This apartment featured laundry facilities and barbecue grills.
Washer
Dryer
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Chicago IL
4.96 mi from city center
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A hot tub, self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. A garden and barbecue grills are also provided.
Hot Tub
Kitchen
A Home Away From Home!

A Home Away From Home!

Chicago IL
11.52 mi from city center
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This vacation home includes a garden and laundry facilities.
Washer
Dryer
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO

Chicago IL
3.39 mi from city center
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A rooftop terrace is featured at this condo, along with a terrace and a garden. Laundry facilities are provided for your convenience.
Kitchen
Washer
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

Chicago IL
4.64 mi from city center
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This apartment features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago IL
1.97 mi from city center
Get rates
This apartment features laundry facilities.
Kitchen
Washer
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3 out of 5
16900 S Halsted St Harvey IL
20.54 mi from city center
$94 nightly
The price is $106 total per night
$106 total
Feb 12 - Feb 13
Total with taxes and fees
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Parking included
Free WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago is a city with many nicknames. The Windy City’s impressive skyline glitters across Lake Michigan, inspiring Carl Sandburg to dub it the City of Big Shoulders when it became the birthplace of the skyscraper. As the home of a rich Blues music tradition, Chicago has also been called Toddlin’ Town and Sweet Home Chicago by voices such as Frank Sinatra and Robert Johnson. Get to know the many names of faces of this great city like a local from our Chicago vacation rentals.

The Local Life

Locals know that exploring Chicago’s best kept secrets is about digging deeper. Sure, try the obligatory Chicago dog, but then head to that corner gourmet dog store for something completely unique, like a chicken, apple, and cranberry dog. Go ahead, wolf it down. We won’t judge.

Enjoy views of famous buildings such as the John Hancock Center, Tribune Tower, and Chicago Water Tower, or be part of the skyline at Embassy Suites Chicago Downtown Magnificent Mile. Locals love the area because it’s so close to the Chicago Riverwalk and the famous Millennium Park.

The Chicago Institute of Art draws admirers from around the world, but the Museum of Contemporary Photography and the Chicago Cultural Center provide inspiration for those who are willing to venture off the beaten path. Luckily, the Ginosi Basics Loop Apartel is close by and features a classy lobby that’s photogenic enough for your own photography exhibit on social media. You can call that shot Untitled #4, or simply #Chicagovacation.

See a side of Chicago most visitors miss, then relax in one of Travelocity’s vacation rentals, where it feels like Sweet Home Chicago.