Compare Chicago Villas

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Featured Villas in Chicago

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

Guests of this villa enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and barbecue grills.

Charming Retreat in the Heart of Des Plaines by RedAwning

At this villa, guests have access to a gym, laundry facilities, and barbecue grills.

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

At this villa, guests have access to a sauna, free WiFi in public areas, and an arcade/game room. A stay here includes free parking. This smoke-free villa also has barbecue grills.

Kitchen

Pet friendly

At this villa, guests have access to features like laundry facilities.

Washer

Dryer

Elegant Riverwoods Escape w/ Private Sauna!

Guests staying at this villa enjoy free WiFi in public areas, an arcade/game room, and barbecue grills. You can put free offsite parking to good use if you drive.

Pet friendly

Free WiFi

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Chicago

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

$92 nightly

$108 total

Dec 18 - Dec 19

Total with taxes and fees

8.4/10 Very Good! (5,366 reviews)

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

$106 nightly

$124 total

Dec 17 - Dec 18

Total with taxes and fees

8.8/10 Excellent! (3,435 reviews)

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

$127 nightly

$149 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

9.2/10 Wonderful! (2,109 reviews)

Luxury Villas

Book luxury villas in Chicago
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Chicago. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Chicago, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Chicago
You won’t have a problem finding your own space in Chicago. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Chicago on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Chicago rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Chicago Villas essential information

Accommodation	7 Villas
Lowest Price	$108
Highest Price	$149
Popular accommodation	HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12, Charming Retreat in the Heart of Des Plaines by RedAwning, Hot Tub & Sauna: Hoffman Estates Villa in Elgin!, ▌360° City Skyline Chicago ▌ , Elegant Riverwoods Escape w/ Private Sauna!