Illinois Luxury Vacations
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Top Luxury vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
found 3 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
5* Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
found 3 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
3 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
4 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Oct 9 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
Top Luxury Illinois Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
The price is ￥69,754 per night from Aug 18 to Aug 19
￥69,754
￥81,885 total
Aug 18 - Aug 19
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 ...
9.2/10 Wonderful! (1,652 reviews)
"Just a great property- really a 5 star experience-great location"
Reviewed on Jul 20, 2025
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
The price is ￥77,679 per night from Aug 10 to Aug 11
￥77,679
￥91,187 total
Aug 10 - Aug 11
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! (1,003 reviews)
A touch of Class
"We had an absolutely wonderful time from the moment we were greeted to the moment we were escorted to our car. It will be our go to place when we visit Chicago in November. Thank you for a wonderful stay!"
Reviewed on Jul 14, 2025
The Peninsula Chicago
108 East Superior Street, Chicago, IL
The price is ￥93,006 per night from Aug 10 to Aug 11
￥93,006
￥109,179 total
Aug 10 - Aug 11
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 ...
9.8/10 Exceptional! (1,003 reviews)
"Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed."
Reviewed on Jul 15, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.