Chicago Villa Rentals & Homes
Find villas near Chicago - We found 13 exact matches
About Chicago Villa Rentals on Ski Hotels
Ski Hotels has more than 13 villas near Chicago. These rentals have all the luxury accoutrements to give you comfort, including amenities such as - private swimming pools, WIFI, spas, hot tubs, and more.
Ski Hotels has a wide range of villa rentals near Chicago, and there are different options for families, friends, or even couples. These rentals come in unique styles or sizes that would definitely suit your needs.
Ski Hotels offers expectational rental villas that are out of the ordinary and not found elsewhere, whether you are traveling on a beachfront, seaside, mountain, or any destination. Ski Hotels is an all-in-one travel platform that matches you with the perfect rental villa in Chicago for your dream vacation, including top travel locations in the USA & the Rest of the World. Many have private pools, luxury bedrooms, and even features like tennis courts, beach volleyball, spas, fitness clubs & more.
Ski Hotels Villas are available for last-minute bookings and may include special offers for Airbnb, VRBO & Ski Hotels-style villas. So find your last-minute getaway today with Ski Hotels in Chicago, and get ready to enjoy maximum comfort on your next holiday.
Frequently Asked Questions About Chicago Villa Rentals
What is the rate per night for renting a villa near Chicago?
At Skihotels, the average rental fee for standard villas in Chicago is $812 per night. Skihotels 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.
Do you have a villa in Chicago that allows pets?
Yes, here are the top villas rentals in Chicago that are pet friendly:
- HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
- City Villa Sleeps 10-20 Free TV & Parking
- Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!
- Villa D' Citta
Are there any rental villas in Chicago that are suitable for families?
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.
Do your rental villas in Chicago have indoor swimming pools?
Based on the 2026 data from our Skihotels site, there are more than 13 private swimming pools or villas with indoor pools in or near Chicago.
Do the villas in Chicago have hot tubs?
There are 13 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 Skihotels