Search Holiday Rentals in Chicago
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Top Holiday Rentals in Chicago

Sentral Michigan Avenue
Sentral Michigan Avenue
9.2 out of 10, Wonderful, (875)
The price is ฿4,665
฿6,430 total
includes taxes & fees
2 Sept - 3 Sept

Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
8.2 out of 10, Very good, (341)
The price is ฿4,113
฿4,828 total
includes taxes & fees
1 Sept - 2 Sept

Level Chicago – Old Town
Level Chicago – Old Town
9.0 out of 10, Wonderful, (338)

Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
9.4 out of 10, Exceptional, (469)

The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy
9.6 out of 10, Exceptional, (189)

Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
8.8 out of 10, Excellent, (613)
The price is ฿3,561
฿4,180 total
includes taxes & fees
2 Sept - 3 Sept

Kasa South Loop Chicago
Kasa South Loop Chicago
9.4 out of 10, Exceptional, (330)

The Gem Museum Suites
The Gem Museum Suites
9.4 out of 10, Exceptional, (83)
The price is ฿6,693
฿7,662 total
includes taxes & fees
2 Sept - 3 Sept
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Chicago Hotel Reviews

Hilton Chicago
10/10 Excellent
Find out more about Chicago
Find out more about Chicago
Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:
- View our selection of featured holiday rentals in Chicago
- Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Chicago while they last
Look no further and take a look at our great range of rental properties in Chicago!