Vacation rentals in Chicago

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

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
$220 nightly
The price is $258 total per night
$258 total
Oct 5 - Oct 6
Total with taxes and fees
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
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place, Chicago, IL
1 mi from city center
$360 nightly
The price is $423 total per night
$423 total
Sep 29 - Sep 30
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
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
$278 nightly
The price is $327 total per night
$327 total
Oct 19 - Oct 20
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
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.2 mi from city center
$186 nightly
The price is $219 total per night
$219 total
Oct 9 - Oct 10
Total with taxes and fees
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 by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 out of 5
1436 West Randolph Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.84 mi from city center
$135 nightly
The price is $159 total per night
$159 total
Oct 19 - Oct 20
Total with taxes and fees
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
Kasa South Loop Chicago

Kasa South Loop Chicago

4 out of 5
900 S Clark Street, Chicago, IL
0.7 mi from city center
Get rates
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 by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 out of 5
555 West Jackson Boulevard, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.74 mi from city center
$186 nightly
The price is $219 total per night
$219 total
Oct 26 - Oct 27
Total with taxes and fees
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.
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
1431 W Taylor St, Chicago, IL
1.95 mi from city center
Get rates
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
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 out of 5
61 West Erie Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$169 nightly
The price is $199 total per night
$199 total
Oct 19 - Oct 20
Total with taxes and fees
This aparthotel includes free WiFi in public areas and concierge services.
Kitchen
Free WiFi
Kasa River North Chicago

Kasa River North Chicago

4 out of 5
808 N Wells St, Chicago, IL
1.16 mi from city center
$292 nightly
The price is $343 total per night
$343 total
Oct 5 - Oct 6
Total with taxes and fees
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.
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
11.79 mi from city center
$221 nightly
The price is $252 total per night
$252 total
Oct 6 - Oct 7
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
Wrigleyville Suites

Wrigleyville Suites

2 out of 5
3727 N Clifton Ave, Chicago, IL
5 mi from city center
Get rates
This aparthotel features free WiFi in public areas, a garden, and laundry facilities. A virtual front desk are provided for your convenience.
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
Sep 28 - Sep 29
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
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 out of 5
19 South Wabash Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.13 mi from city center
$179 nightly
The price is $210 total per night
$210 total
Oct 1 - Oct 2
Total with taxes and fees
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.
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 out of 5
South Dearborn Street, Van Buren, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.31 mi from city center
$148 nightly
The price is $174 total per night
$174 total
Oct 20 - Oct 21
Total with taxes and fees
A rooftop terrace is featured at this aparthotel, along with luggage storage and a virtual front desk.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Chicago
View all properties
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.