2613+ Private Villas and Holiday Rentals in Central Chicago |
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Central Chicago Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Central Chicago

Discover more than 2613 vacation rentals available in Central 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 Central Chicago.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Central 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 Central Chicago. On average, places to stay near Central Chicago offer 763.34 ft², with nightly prices averaging ZA R7,931.

With Casai, finding and comparing holiday rentals in Central 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 Central Chicago

Type Count
Holiday Apartments 1629
Vacation Homes 372
Villas 4

Use these Quick Filters to Find a Holiday Rental in Central 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 Central Chicago.

Weather in Central Chicago, IL

View the weather forecast for Central Chicago before booking your Central 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 Central Chicago, IL

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


Navy Pier
McCormick Place
Millennium Park
Soldier Field
Willis Tower
Art Institute of Chicago
Grant Park
John G. Shedd Aquarium
Chicago Theatre
Chicago Riverwalk
Field Museum of Natural History
John Hancock Center
Water Tower Place
House of Blues Chicago
Merchandise Mart
Chicago Children's Museum
Northwestern Memorial Hospital
Cloud Gate
Wintrust Arena
Aon Center

Other Places to Stay in Central Chicago, IL


Chicago 7,244 Properties
Chicago 4,211 Properties
Downtown Chicago 1,791 Properties
Near North Side 818 Properties
The Loop 775 Properties
River North 484 Properties
South Side 378 Properties
South Loop 372 Properties
Near South Side 360 Properties
Prairie District 256 Properties
Streeterville 202 Properties
Rush and Division 77 Properties

Frequently Asked Questions About Central Chicago?

What are the top holiday rentals in Central Chicago?

With numerous options available in Central Chicago, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Central Chicago:

How many holiday rentals have private pools in Central Chicago?

Discover a selection of holiday rentals with private pools near Central 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 Central Chicago are best for families?

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

How many Casai.co.za holiday rentals are available in Central Chicago?

As of 2025, Casai boasts over 2613 properties listed in the Central Chicago area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Central Chicago.

Nearby Neighborhood (16) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1791
Near North Side Vacation Rentals in Chicago, Illinois 818
The Loop Vacation Rentals in Chicago, Illinois 775
River North Vacation Rentals in Chicago, Illinois 484
South Loop Vacation Rentals in Chicago, Illinois 372
Near South Side Vacation Rentals in Chicago, Illinois 360
Near West Side Vacation Rentals in Chicago, Illinois 331
West Town Vacation Rentals in Chicago, Illinois 283
Streeterville Vacation Rentals in Chicago, Illinois 202
West Loop Vacation Rentals in Chicago, Illinois 198
Lincoln Park Vacation Rentals in Chicago, Illinois 143
Bronzeville Vacation Rentals in Chicago, Illinois 100
Old Town Vacation Rentals in Chicago, Illinois 53
River West Vacation Rentals in Chicago, Illinois 52
Gold Coast Vacation Rentals in Chicago, Illinois 39
Chinatown Vacation Rentals in Chicago, Illinois 3053

People Also Ask

There are 2613 Central Chicago, IL Holiday Rentals

Recently Booked Holiday Rentals in Central Chicago