
Chicago Luxury Vacations
Luxury hotels in Chicago

Trump International Hotel & Tower Chicago

The Langham, Chicago

The Peninsula Chicago
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.
Hotel themes
- Hotels with WiFi in Chicago
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- Hotels with Free Parking in Chicago
- Hotels with Bar in Chicago
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- Hotels with Pool in Chicago
- Cheap Hotels in Chicago