Chicago Holiday Rentals

Compare Villas, Resorts, & Rentals in Chicago, Illinois, USA

10.0 (2 Reviews)
1 Bedroom 2 Guests
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10.0 (20 Reviews)
1 Bedroom 2 Guests
10.0 (2 Reviews)
2 Bedrooms 2 Guests
10.0 (6 Reviews)
1 Bedroom 5 Guests
10.0 (1 Review)
1 Bedroom 3 Guests
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10.0 (16 Reviews)
1 Bedroom 2 Guests
From CA $267 per night
2.0 (1 Review)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
9.8 (17 Reviews)
2 Bedrooms 4 Guests
From CA $161 per night
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10.0 (12 Reviews)
1 Bedroom 4 Guests
9.8 (15 Reviews)
2 Bedrooms 5 Guests
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10.0 (10 Reviews)
3 Bedrooms 10 Guests
9.4 (6 Reviews)
1 Bedroom 3 Guests
From CA $370 per night
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10.0 (6 Reviews)
3 Bedrooms 8 Guests
8.0 (3 Reviews)
3 Bedrooms 4 Guests
From CA $1,003 per night
10.0 (6 Reviews)
4 Bedrooms 8 Guests
From CA $534 per night
New
1 Bedroom 1 Guest
From CA $155 per night
10.0 (6 Reviews)
2 Bedrooms 6 Guests
From CA $361 per night
New
1 Bedroom 2 Guests
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10.0 (5 Reviews)
1 Bedroom 2 Guests
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10.0 (5 Reviews)
1 Bedroom 2 Guests
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10.0 (4 Reviews)
3 Bedrooms 6 Guests
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10.0 (4 Reviews)
4 Bedrooms 15 Guests
New
2 Bedrooms 5 Guests
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10.0 (4 Reviews)
3 Bedrooms 7 Guests
10.0 (4 Reviews)
2 Bedrooms 4 Guests
From CA $191 per night
New
1 Bedroom 2 Guests
From CA $338 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
New
2 Bedrooms 5 Guests
From CA $2,184 per night
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10.0 (3 Reviews)
13 Bedrooms 32 Guests
From CA $258 per night
10.0 (47 Reviews)
2 Bedrooms 6 Guests
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10.0 (3 Reviews)
3 Bedrooms 8 Guests
From CA $278 per night
10.0 (46 Reviews)
2 Bedrooms 4 Guests
From CA $383 per night
10.0 (44 Reviews)
2 Bedrooms 5 Guests
From CA $196 per night
10.0 (37 Reviews)
1 Bedroom 3 Guests
10.0 (31 Reviews)
2 Bedrooms 8 Guests
From CA $490 per night
10.0 (20 Reviews)
2 Bedrooms 4 Guests
10.0 (17 Reviews)
1 Bedroom 2 Guests
9.8 (15 Reviews)
2 Bedrooms 7 Guests
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10.0 (3 Reviews)
6 Bedrooms 20 Guests
9.8 (10 Reviews)
1 Bedroom 2 Guests
From CA $431 per night
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10.0 (3 Reviews)
1 Bedroom 4 Guests
From CA $333 per night
New
1 Bedroom 2 Guests
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10.0 (3 Reviews)
2 Bedrooms 6 Guests
New
3 Bedrooms 10 Guests
10.0 (3 Reviews)
3 Bedrooms 6 Guests
From CA $404 per night
10.0 (3 Reviews)
2 Bedrooms 2 Guests
9.6 (19 Reviews)
2 Bedrooms 6 Guests
|
10.0 (2 Reviews)
5 Bedrooms 10 Guests
9.6 (13 Reviews)
2 Bedrooms 6 Guests
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10.0 (2 Reviews)
3 Bedrooms 8 Guests
9.6 (4 Reviews)
1 Bedroom 4 Guests
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
9.4 (29 Reviews)
2 Bedrooms 6 Guests
|
10.0 (2 Reviews)
4 Bedrooms 10 Guests

About Casai's Private Villas and Holiday Rentals in Chicago

Discover more than 10573 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 754.96 ft², with nightly prices averaging CA $500.

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.

Frequently Asked Questions About Chicago?

What are the top holiday rentals in Chicago?

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

As of 2025, Casai boasts over 10573 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 1794
Near North Side Vacation Rentals in Chicago, Illinois 818
The Loop Vacation Rentals in Chicago, Illinois 776
River North Vacation Rentals in Chicago, Illinois 486
South Loop Vacation Rentals in Chicago, Illinois 375
Near South Side Vacation Rentals in Chicago, Illinois 363
Lakeview Vacation Rentals in Chicago, Illinois 247
West Loop Vacation Rentals in Chicago, Illinois 200
Lincoln Park Vacation Rentals in Chicago, Illinois 147
Hyde Park Vacation Rentals in Chicago, Illinois 86
Logan Square Vacation Rentals in Chicago, Illinois 76
Rogers Park Vacation Rentals in Chicago, Illinois 67
O'Hare Vacation Rentals in Chicago, Illinois 66
Edgewater Vacation Rentals in Chicago, Illinois 55
Wrigleyville Vacation Rentals in Chicago, Illinois 46
Wicker Park Vacation Rentals in Chicago, Illinois 42