Chicago, IL Holiday Rentals

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Compare Holiday Rentals, Villas & Resorts in Chicago

8,154 villas and rentals
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About Casai's Private Villas and Holiday Rentals in Chicago

Discover more than 8154 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 764.42 ft², with nightly prices averaging US $380.

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 6,551 Properties
Central Chicago 1,514 Properties
Downtown Chicago 1,428 Properties
West Side 791 Properties
The Loop 646 Properties
Near North Side 589 Properties
North Side 557 Properties
River North 355 Properties
Far North Side 338 Properties
Near West Side 329 Properties
West Town 314 Properties
South Loop 297 Properties

There are 8154 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.nz holiday rentals are available in Chicago?

As of 2026, Casai boasts over 8154 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 1428
The Loop Vacation Rentals in Chicago, Illinois 646
Near North Side Vacation Rentals in Chicago, Illinois 589
River North Vacation Rentals in Chicago, Illinois 355
South Loop Vacation Rentals in Chicago, Illinois 297
Near South Side Vacation Rentals in Chicago, Illinois 278
Lakeview Vacation Rentals in Chicago, Illinois 245
West Loop Vacation Rentals in Chicago, Illinois 192
Lincoln Park Vacation Rentals in Chicago, Illinois 133
Hyde Park Vacation Rentals in Chicago, Illinois 76
Edgewater Vacation Rentals in Chicago, Illinois 62
Rogers Park Vacation Rentals in Chicago, Illinois 58
Wrigleyville Vacation Rentals in Chicago, Illinois 56
Logan Square Vacation Rentals in Chicago, Illinois 55
O'Hare Vacation Rentals in Chicago, Illinois 46
Wicker Park Vacation Rentals in Chicago, Illinois 37