Illinois Luxury Vacations

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Top Luxury vacation packages in Illinois

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Waldorf Astoria Chicago
Park Hyatt Chicago
Fairmont Chicago at Millennium Park
The Peninsula Chicago
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5* Luxury vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Waldorf Astoria Chicago
The Peninsula Chicago
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See all available trips from Tokyo to Illinois
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3 Night Luxury vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
Park Hyatt Chicago
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4 Night Luxury vacations in Illinois

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton
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Top Luxury Illinois Hotels

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave, Chicago, IL
  • 10 min drive from Wrigley Field
The price is ¥65,921 per night from Nov 2 to Nov 3
¥65,921
¥77,386 total
Nov 2 - Nov 3
includes taxes & fees
Trump International Hotel & Tower Chicago is a lush 5-star boutique property where you can be treated to deep soaking bathtubs and pillowtop beds. The spa, indoor ...
9.4/10 Exceptional! (1,763 reviews)
The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home.

Reviewed on Oct 26, 2025

Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue, Chicago, IL
  • 10 min drive from Wrigley Field
The price is ¥76,468 per night from Nov 16 to Nov 17
¥76,468
¥89,766 total
Nov 16 - Nov 17
includes taxes & fees
Enjoy a posh stay at The Langham, Chicago, where you'll find deep soaking bathtubs and a champagne service. Deluxe amenities at this hotel include a spa, an ...
9.6/10 Exceptional! (1,016 reviews)
Great beds

Reviewed on Oct 14, 2025

The Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street, Chicago, IL
  • 9 min drive from Wrigley Field
The price is ¥87,436 per night from Nov 16 to Nov 17
¥87,436
¥102,642 total
Nov 16 - Nov 17
includes taxes & fees
Treat yourself to some luxurious accommodations at The Peninsula Chicago, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe ...
9.6/10 Exceptional! (1,019 reviews)
Great

Reviewed on Oct 22, 2025

The Peninsula Chicago
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.