Compare Villas, Resorts, & Rentals in Chicago, Illinois, USA
About Casai's Private Villas and Holiday Rentals in Chicago
Discover more than 11547 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 741.88 ft², with nightly prices averaging CA $462.
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 in Chicago, IL
Frequently Asked Questions About Chicago?
What are the top holiday rentals in Chicago?
- The Sono Chicago
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 55th Floor Penthouse with Award-Winning Views
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- 51st Floor MagMile Penthouse Views Balcony Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- NEW LUXURY PENTHOUSE CONDO
How many Casai.ca holiday rentals are available in Chicago?
As of 2026, Casai boasts over 11547 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 | 1541 |
| The Loop Vacation Rentals in Chicago, Illinois | 711 |
| Near North Side Vacation Rentals in Chicago, Illinois | 613 |
| South Loop Vacation Rentals in Chicago, Illinois | 367 |
| Near South Side Vacation Rentals in Chicago, Illinois | 352 |
| River North Vacation Rentals in Chicago, Illinois | 329 |
| Lakeview Vacation Rentals in Chicago, Illinois | 267 |
| West Loop Vacation Rentals in Chicago, Illinois | 217 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 155 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 103 |
| Logan Square Vacation Rentals in Chicago, Illinois | 89 |
| Edgewater Vacation Rentals in Chicago, Illinois | 77 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 75 |
| O'Hare Vacation Rentals in Chicago, Illinois | 51 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 49 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 47 |
