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
Charming Retreat in the Heart of Des Plaines by RedAwning

Charming Retreat in the Heart of Des Plaines by RedAwning

Des Plaines IL
At this villa, guests have access to a gym, laundry facilities, and barbecue grills.
Washer
Dryer
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

3.5 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
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

    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue Chicago IL
    $135 nightly
    The price is $161 total per night from May 25 to May 26
    $161 total
    May 25 - May 26
    Total with taxes and fees
    8/10 Very Good! (10,134 reviews)
    Hotel Riu Plaza Chicago

    Hotel Riu Plaza Chicago

    150 East Ontario Street Chicago IL
    $156 nightly
    The price is $185 total per night from May 25 to May 26
    $185 total
    May 25 - May 26
    Total with taxes and fees
    9.4/10 Exceptional! (4,221 reviews)
    The Chicago Hotel Collection - Magnificent Mile

    The Chicago Hotel Collection - Magnificent Mile

    166 E Superior Street Chicago IL
    $123 nightly
    The price is $146 total per night from May 25 to May 26
    $146 total
    May 25 - May 26
    Total with taxes and fees
    7.8/10 Good! (1,466 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
6 Villas
Lowest Price
$146
Highest Price
$185
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!, Elegant Riverwoods Escape w/ Private Sauna!