Chicago Holiday Rentals

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Compare Villas, Resorts, & Rentals in Chicago

12,737 villas and rentals
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About Casai's Private Villas and Holiday Rentals in Chicago

Discover more than 12737 vacation rentals available in Chicago. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chicago.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chicago, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chicago. On average, places to stay near Chicago offer 747.62 ft², with nightly prices averaging US $361.

With Casai, finding and comparing holiday rentals in Chicago is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Other places to stay near the Chicago, IL


Cook County 4,863 Properties
Chicago 3,729 Properties
Central Chicago 1,480 Properties
Downtown Chicago 1,385 Properties
West Side 766 Properties
The Loop 620 Properties
Near North Side 580 Properties
Lake County 573 Properties
North Side 533 Properties
DuPage County 459 Properties
River North 345 Properties
Far North Side 315 Properties

There are 12737 Chicago, IL Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Chicago

Frequently Asked Questions About Chicago?

What are the top holiday rentals in Chicago?

With numerous options available in Chicago, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chicago:

How many Casai.com holiday rentals are available in Chicago?

As of 2026, Casai boasts over 12737 properties listed in the Chicago area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chicago.

Nearby Neighborhood (16)

NeighborhoodProperty Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1385
The Loop Vacation Rentals in Chicago, Illinois 620
Near North Side Vacation Rentals in Chicago, Illinois 580
River North Vacation Rentals in Chicago, Illinois 345
South Loop Vacation Rentals in Chicago, Illinois 295
Near South Side Vacation Rentals in Chicago, Illinois 276
Lakeview Vacation Rentals in Chicago, Illinois 230
West Loop Vacation Rentals in Chicago, Illinois 183
Lincoln Park Vacation Rentals in Chicago, Illinois 127
Hyde Park Vacation Rentals in Chicago, Illinois 76
Edgewater Vacation Rentals in Chicago, Illinois 63
Logan Square Vacation Rentals in Chicago, Illinois 56
Rogers Park Vacation Rentals in Chicago, Illinois 55
Wrigleyville Vacation Rentals in Chicago, Illinois 53
O'Hare Vacation Rentals in Chicago, Illinois 49
Wicker Park Vacation Rentals in Chicago, Illinois 39