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
The price is $178 per night
$178
includes taxes & fees
$152 per night
Mar 26 - Mar 27
This aparthotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 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
Sonder South Wabash

Sonder South Wabash

3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
1.2 mi from city center
The price is $110 per night
$110
includes taxes & fees
$93 per night
Apr 16 - Apr 17
A gym is featured at this aparthotel, along with luggage storage and locker space. Concierge services and a virtual front desk are also provided.
Kitchen
Washer
Sonder Market Hall

Sonder Market Hall

3.5 out of 5
1436 West Randolph Street, Chicago, IL
1.84 mi from city center
The price is $125 per night
$125
includes taxes & fees
$107 per night
Apr 16 - Apr 17
A nightclub and a gym are featured at this smoke-free aparthotel. WiFi in public areas is free. Concierge services are provided for your convenience.
Kitchen
Free WiFi
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
The price is $215 per night
$215
includes taxes & fees
$183 per night
Mar 31 - Apr 1
A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.
Pool
Kitchen
Sonder The Burnham Apartments

Sonder The Burnham Apartments

3.5 out of 5
555 West Jackson Boulevard, Chicago, IL
0.74 mi from city center
The price is $147 per night
$147
includes taxes & fees
$126 per night
Apr 22 - Apr 23
A gym is featured at this aparthotel, along with free WiFi in public areas and luggage storage. Locker space and concierge services are also provided.
Kitchen
Free WiFi
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place, Chicago, IL
1 mi from city center
Get rates
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
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
Sonder Jewelers Row

Sonder Jewelers Row

3.5 out of 5
19 South Wabash Avenue, Chicago, IL
0.13 mi from city center
The price is $114 per night
$114
includes taxes & fees
$97 per night
Apr 15 - Apr 16
Free WiFi in public areas, luggage storage, and locker space are available at this aparthotel. Concierge services and a virtual front desk are also provided.
Kitchen
Washer
Sonder Onterie

Sonder Onterie

3.5 out of 5
446 East Ontario Street, Chicago, IL
1.07 mi from city center
The price is $120 per night
$120
includes taxes & fees
$102 per night
Apr 23 - Apr 24
This apartment features free WiFi in public areas, luggage storage, and concierge services.
Kitchen
Free WiFi
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

3.5 out of 5
1431 W Taylor St, Chicago, IL
1.95 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
Free WiFi
Sonder The Plymouth

Sonder The Plymouth

3.5 out of 5
South Dearborn Street, Van Buren, Chicago, IL
0.32 mi from city center
The price is $115 per night
$115
includes taxes & fees
$98 per night
Apr 23 - Apr 24
A rooftop terrace is featured at this aparthotel, along with luggage storage and a virtual front desk.
Kitchen
Washer
Kasa River North Chicago

Kasa River North Chicago

4 out of 5
808 N Wells St, Chicago, IL
1.16 mi from city center
The price is $111 per night
$111
includes taxes & fees
$94 per night
Mar 31 - Apr 1
This aparthotel features a gym and a seasonal outdoor pool. Business travelers can take advantage of the business center. There's a rooftop terrace on site, and concierge services and a virtual front desk are also offered.
Pool
Kitchen
Sonder The Opal

Sonder The Opal

3.5 out of 5
61 West Erie Street, Chicago, IL
0.91 mi from city center
The price is $107 per night
$107
includes taxes & fees
$92 per night
Apr 23 - Apr 24
This aparthotel includes free WiFi in public areas and concierge services.
Kitchen
Free WiFi
Comfort Inn Chicago Wind Creek Casino

Comfort Inn Chicago Wind Creek Casino

2.5 out of 5
16900 S Halsted St, Harvey, IL
Free Cancellation
Reserve now, pay when you stay
20.54 mi from city center
The price is $93 per night
$93
includes taxes & fees
$82 per night
Apr 1 - Apr 2
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
Sonder Greektown

Sonder Greektown

3.5 out of 5
314 South Halsted Street, Chicago, IL
1.03 mi from city center
The price is $140 per night
$140
includes taxes & fees
$119 per night
Apr 20 - Apr 21
A rooftop terrace is featured at this aparthotel, along with free WiFi in public areas and concierge services. A virtual front desk are provided for your convenience.
Kitchen
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.