10867+ Private Villas and Holiday Rentals in Chicago |
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Chicago Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chicago

Discover more than 10867 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 790.35 ft², with nightly prices averaging US $369.

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.

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Top Accommodation Types in Chicago

Type Count
Holiday Apartments 5185
Vacation Homes 3241
Cottages 44
Villas 22

Use these Quick Filters to Find a Holiday Rental in Chicago

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chicago.

Weather in Chicago, IL

View the weather forecast for Chicago before booking your Chicago Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chicago, IL

Casai offers a large selection of top attractions around Chicago . Research things to do on your vacation before you visit Chicago.


Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field
Willis Tower
Art Institute of Chicago
Naval Base Great Lakes
United Center
Grant Park
John G. Shedd Aquarium
Chicago Museum of Science and Industry
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
Six Flags Great America
University of Chicago
Brookfield Zoo
Northwestern University

Other Places to Stay in Chicago, IL


Cook County 5,993 Properties
Chicago 4,568 Properties
Central Chicago 1,958 Properties
Downtown Chicago 1,766 Properties
Near North Side 822 Properties
West Side 812 Properties
The Loop 745 Properties
North Side 697 Properties
Lake County 560 Properties
DuPage County 537 Properties
River North 481 Properties
Far North Side 414 Properties

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 holiday rentals have private pools in Chicago?

Discover a selection of holiday rentals with private pools near Chicago with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Chicago are best for families?

If you're searching for a family-friendly holiday home in Chicago, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chicago:

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

As of 2025, Casai boasts over 10867 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) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1766
Near North Side Vacation Rentals in Chicago, Illinois 822
The Loop Vacation Rentals in Chicago, Illinois 745
River North Vacation Rentals in Chicago, Illinois 481
South Loop Vacation Rentals in Chicago, Illinois 401
Near South Side Vacation Rentals in Chicago, Illinois 389
Lakeview Vacation Rentals in Chicago, Illinois 301
West Loop Vacation Rentals in Chicago, Illinois 199
Lincoln Park Vacation Rentals in Chicago, Illinois 163
Hyde Park Vacation Rentals in Chicago, Illinois 124
Logan Square Vacation Rentals in Chicago, Illinois 79
Rogers Park Vacation Rentals in Chicago, Illinois 73
O'Hare Vacation Rentals in Chicago, Illinois 69
Edgewater Vacation Rentals in Chicago, Illinois 65
Wicker Park Vacation Rentals in Chicago, Illinois 51
Wrigleyville Vacation Rentals in Chicago, Illinois 50

People Also Ask

There are 10867 Chicago, IL Holiday Rentals

Recently Booked Holiday Rentals in Chicago