Chicago Holiday Rentals

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Compare Holiday Rentals, Villas & Resorts in Chicago

8,043 villas and rentals
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About Casai's Private Villas and Holiday Rentals in Chicago

Discover more than 8043 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 757.71 ft², with nightly prices averaging R6,324.

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 in Chicago, IL


Chicago 6,199 Properties
Central Chicago 1,446 Properties
Downtown Chicago 1,352 Properties
West Side 760 Properties
The Loop 613 Properties
Near North Side 556 Properties
North Side 504 Properties
River North 324 Properties
Near West Side 314 Properties
West Town 308 Properties
Far North Side 300 Properties
South Loop 295 Properties

There are 8043 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.co.za holiday rentals are available in Chicago?

As of 2026, Casai boasts over 8043 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 1352
The Loop Vacation Rentals in Chicago, Illinois 613
Near North Side Vacation Rentals in Chicago, Illinois 556
River North Vacation Rentals in Chicago, Illinois 324
South Loop Vacation Rentals in Chicago, Illinois 295
Near South Side Vacation Rentals in Chicago, Illinois 276
Lakeview Vacation Rentals in Chicago, Illinois 211
West Loop Vacation Rentals in Chicago, Illinois 183
Lincoln Park Vacation Rentals in Chicago, Illinois 125
Edgewater Vacation Rentals in Chicago, Illinois 61
Logan Square Vacation Rentals in Chicago, Illinois 55
Rogers Park Vacation Rentals in Chicago, Illinois 54
Hyde Park Vacation Rentals in Chicago, Illinois 52
Wrigleyville Vacation Rentals in Chicago, Illinois 49
O'Hare Vacation Rentals in Chicago, Illinois 49
Wicker Park Vacation Rentals in Chicago, Illinois 38