Chicago Holiday Rentals

We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.

Destination
Dates
Guests
Search
  • Up-front pricing
  • No markup
  • Trusted partners

Compare Villas, Resorts, & Rentals in Chicago

8,068 villas and rentals
Sort by
See More Properties

About Casai's Private Villas and Holiday Rentals in Chicago

Discover more than 8068 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 760.17 ft², with nightly prices averaging US $383.

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


Chicago 6,368 Properties
Central Chicago 1,496 Properties
Downtown Chicago 1,403 Properties
West Side 764 Properties
The Loop 633 Properties
Near North Side 586 Properties
North Side 525 Properties
River North 351 Properties
Near West Side 315 Properties
Far North Side 310 Properties
West Town 307 Properties
South Loop 295 Properties

There are 8068 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 8068 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 1403
The Loop Vacation Rentals in Chicago, Illinois 633
Near North Side Vacation Rentals in Chicago, Illinois 586
River North Vacation Rentals in Chicago, Illinois 351
South Loop Vacation Rentals in Chicago, Illinois 295
Near South Side Vacation Rentals in Chicago, Illinois 276
Lakeview Vacation Rentals in Chicago, Illinois 225
West Loop Vacation Rentals in Chicago, Illinois 184
Lincoln Park Vacation Rentals in Chicago, Illinois 129
Hyde Park Vacation Rentals in Chicago, Illinois 72
Edgewater Vacation Rentals in Chicago, Illinois 60
Rogers Park Vacation Rentals in Chicago, Illinois 55
Logan Square Vacation Rentals in Chicago, Illinois 53
Wrigleyville Vacation Rentals in Chicago, Illinois 53
O'Hare Vacation Rentals in Chicago, Illinois 47
Gold Coast Vacation Rentals in Chicago, Illinois 38