Book Chicago Luxury Vacations

Best Luxury vacations in Chicago

Trump International Hotel & Tower Chicago
21c Museum Hotel Chicago
Hotel Arista
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Luxury vacation packages for 3 nights

Trump International Hotel & Tower Chicago
21c Museum Hotel Chicago
Fairmont Chicago at Millennium Park
Prices and availability subject to change. Additional terms may apply.

Luxury vacation packages for 4 nights

LondonHouse Chicago, Curio Collection by Hilton
Virgin Hotels Chicago
21c Museum Hotel Chicago
Prices and availability subject to change. Additional terms may apply.

Luxury vacation packages for 5 nights

LondonHouse Chicago, Curio Collection by Hilton
Congress Plaza Hotel
Trump International Hotel & Tower Chicago
Prices and availability subject to change. Additional terms may apply.

Luxury vacation packages for 6-7 nights

Congress Plaza Hotel
Palmer House a Hilton Hotel
Trump International Hotel & Tower Chicago
Prices and availability subject to change. Additional terms may apply.

Luxury hotels in Chicago

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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.

Book Chicago luxury vacations

You want the best of everything in life, and that includes when you travel. Get the full treatment on your next trip, with five-star service, delicious dining and tons of extra amenities to pamper you like royalty. With luxury Chicago vacations, “living the dream” isn’t just a saying. You really can make your dreams a reality—and then dream even bigger. You’ll never look at vacations the same way again.

Experience the ultimate luxury
With silky soft sheets and plush pillows, you’ve never slept better than you will in your luxury hotel room. But when the sun peeks through the curtains, you’ll jump out of bed. That’s because in Chicago, real life is even better than dreams. Grab yourself a gourmet coffee and get to the first task of the day—even if that just means a leisurely brunch, or getting to your spa appointment. On luxury vacations in Chicago, the day is yours. We’re just here to help you have your perfect 5-star getaway.

  • Live a life of luxury: We have tons of highly rated hotels, where you’ll find all the upscale amenities you want. You could find splendid spas, ritzy restaurants, deluxe bath products and more.
  • Bundles for your budget: You don’t have to be a big spender to find luxury vacation packages—but you can be if you want to. When you bundle your flight and hotel with Orbitz, you know you’re getting a great deal. 

Your luxury vacation starts now. Booking on Orbitz is so easy, you’ll feel like you have a personal assistant…and once you’re in Chicago, you just might. The only problem in your future: You won’t want to go home!

How much does it cost to fly to Chicago?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.