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Best Luxury vacations in Chicago

Luxury vacation packages for 3 nights

Luxury vacation packages for 4 nights

Luxury vacation packages for 5 nights

Luxury vacation packages for 6-7 nights

Luxury hotels in Chicago

The Langham, Chicago
The Langham, Chicago
5.0 out of 5.0 330 North Wabash Avenue, Chicago, IL
Free Cancellation
$278
4.9/5 (73 reviews)

Very accessible and classy. Spa and restaurant options a plus.

Reviewed on Dec 2, 2019
LuxurySpaDining
The Peninsula Chicago
The Peninsula Chicago
5.0 out of 5.0 108 East Superior Street, Chicago, IL
Free Cancellation
$399
4.9/5 (88 reviews)

What's not to like, one of the best hotels in the world.

Reviewed on Nov 19, 2019
LuxurySpaFitness Center
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
5.0 out of 5.0 401 N Wabash Ave, Chicago, IL
Free Cancellation
$260
4.7/5 (121 reviews)

The most beautiful hotel I ever seen , we were upgraded to a suite and it was spectacular !

Reviewed on Aug 19, 2019
LuxuryConciergeRoomservice
Thompson Chicago
Thompson Chicago
4.5 out of 5.0 21 East Bellevue, Chicago, IL
Free Cancellation
$143
4.7/5 (123 reviews)

Loved the location. But the safe in the room didn't work. It was very loud air conditioner.

Reviewed on Jul 1, 2019
LuxuryBarDining
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 out of 5.0 20 E Chestnut St, Chicago, IL
Free Cancellation
$119
4.6/5 (209 reviews)

Perfect location. Everything was within a shirt walk, and the hotel itself is absolutely beautiful

Reviewed on Nov 26, 2019
LuxuryConciergeDining
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 out of 5.0 521 North Rush Street, Chicago, IL
Free Cancellation
$134
4.2/5 (21 reviews)

The location was fantastic. Plenty of shops and restaurants within walking distance.

Reviewed on Apr 16, 2019
LuxuryBarConcierge

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!

Luxury hotels with recent reviews

Recently booked Luxury hotels

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.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.