Compare Southwest Side Villas

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Featured Villas in Southwest Side

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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 Southwest Side

    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $89 nightly
    The price is $105 total per night from Jan 5 to Jan 6
    $105 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,504 reviews)
    Silversmith Hotel Chicago Downtown

    Silversmith Hotel Chicago Downtown

    10 S Wabash Ave Chicago IL
    $127 nightly
    The price is $149 total per night from Jan 4 to Jan 5
    $149 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (2,133 reviews)
    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St Chicago IL
    $140 nightly
    The price is $160 total per night from Dec 28 to Dec 29
    $160 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.4/10 Very Good! (2,146 reviews)

Luxury Villas

Book luxury villas in Southwest Side
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Southwest Side. 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 Southwest Side, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Southwest Side
You won’t have a problem finding your own space in Southwest Side. 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 Southwest Side on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Southwest Side 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!

Southwest Side Villas essential information

Accommodation
2 Villas
Lowest Price
$105
Highest Price
$160
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

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