Compare Chicago Villas

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Featured Villas in Chicago

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

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

Chicago IL
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 a living plant wall.
Hot Tub
Kitchen
Relaxing Sauna: Hoffman Estates Villa in Elgin!

Relaxing Sauna: Hoffman Estates Villa in Elgin!

4 out of 5
Hoffman Estates IL
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
Washer
Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!

Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!

Chicago IL
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Elegant Riverwoods Escape w/ Private Sauna!

Elegant Riverwoods Escape w/ Private Sauna!

3 out of 5
Deerfield IL
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

    River Hotel

    River Hotel

    75 East Wacker Drive Chicago IL
    $186 nightly
    The price is $221 total per night from Oct 25 to Oct 26
    $221 total
    Oct 25 - Oct 26
    Total with taxes and fees
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue Chicago IL
    $157 nightly
    The price is $187 total per night from Oct 26 to Oct 27
    $187 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8/10 Very Good! (10,253 reviews)
    The Chicago Hotel Collection Ambassador Gold Coast

    The Chicago Hotel Collection Ambassador Gold Coast

    1301 N State Pkwy Chicago IL
    $179 nightly
    The price is $213 total per night from Oct 14 to Oct 15
    $213 total
    Oct 14 - Oct 15
    Total with taxes and fees
    8/10 Very Good! (2,363 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
4 Villas
Lowest Price
$187
Highest Price
$221
Popular accommodation
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12, Relaxing Sauna: Hoffman Estates Villa in Elgin!, Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!, Elegant Riverwoods Escape w/ Private Sauna!