Chicago Villa Rentals & Ski-in/Ski-out Homes

Find villas near Chicago - We found 10 exact matches

About Chicago Villa on SunSkiResorts

Explore a plethora of luxury villas offered by SunSki in the Chicago area. These rentals boast top-notch amenities like private swimming pools, WiFi, hot tubs, and more, ensuring a comfortable and delightful stay.

Whether you're traveling with friends, family, or planning a romantic escape, SunSki provides a variety of villa options to suit your needs in the Chicago area. Each rental features its own unique style and amenities.

SunSki's villas are situated in some of the most coveted destinations globally, including Chicago. Whether you prefer a beachfront, mountain, or seaside retreat, SunSki offers a diverse range of options, many of which include private pools, luxurious bedrooms, and additional amenities like tennis courts and fitness clubs.

With SunSki, finding and booking last-minute villa rentals in Chicago is effortless. Browse our selection of villas and seize special offers and deals on SunSki as well as other leading vacation rental platforms such as Airbnb and VRBO. Make your next holiday truly memorable with SunSki.

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Frequently Asked Questions About Chicago Rental Villas

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Chicago:

At SunSkiResorts, the average rental fee for standard villas in Chicago is $773 per night. SunSki has a large database of quality villas near Chicago that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Yes, here are the top villas rentals in Chicago that are pet friendly:See all pet-friendly vacation rentals in Chicago on SunSkiResorts
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Chicago to find what works for you.
Based on the 2026 data from our SunSkiResorts site, there are more than 10 private swimming pools or villas with indoor pools in or near Chicago.
There are 10 villas in or near Chicago that have hot tubs. The most popular places to stay with hot tubs include:See all holiday vacation rentals in Chicago on SunSkiResorts
Most definitely! There are many luxury villas in Chicago. Use our search filter to discover all of our luxury villas, and choose the one that matches your taste. Sorting by price is another way to find the most expensive villas in Chicago.