8072+ 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 8072 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 788.96 ft², with nightly prices averaging $389.

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 5310
Vacation Homes 1430
Villas 12
Cottages 4

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


Chicago 7,554 Properties
Central Chicago 1,877 Properties
Downtown Chicago 1,694 Properties
West Side 799 Properties
Near North Side 765 Properties
The Loop 725 Properties
North Side 674 Properties
River North 430 Properties
South Side 404 Properties
South Loop 397 Properties
Far North Side 390 Properties
Near South Side 385 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 8072 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 1694
Near North Side Vacation Rentals in Chicago, Illinois 765
The Loop Vacation Rentals in Chicago, Illinois 725
River North Vacation Rentals in Chicago, Illinois 430
South Loop Vacation Rentals in Chicago, Illinois 397
Near South Side Vacation Rentals in Chicago, Illinois 385
Lakeview Vacation Rentals in Chicago, Illinois 290
West Loop Vacation Rentals in Chicago, Illinois 204
Lincoln Park Vacation Rentals in Chicago, Illinois 159
Hyde Park Vacation Rentals in Chicago, Illinois 123
Logan Square Vacation Rentals in Chicago, Illinois 72
Rogers Park Vacation Rentals in Chicago, Illinois 68
O'Hare Vacation Rentals in Chicago, Illinois 60
Edgewater Vacation Rentals in Chicago, Illinois 56
Wrigleyville Vacation Rentals in Chicago, Illinois 49
Wicker Park Vacation Rentals in Chicago, Illinois 48

People Also Ask

There are 8072 Chicago, IL Holiday Rentals

Recently Booked Holiday Rentals in Chicago