Illinois Luxury Vacations
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Top Luxury vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was NT$21,634, price is now NT$17,955 per person
NT$17,955
per person
Apr 28 - May 1
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 2026/3/9
Hilton Chicago
Downtown Chicago
Price was NT$24,435, price is now NT$20,668 per person
NT$20,668
per person
Apr 28 - May 1
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on 2026/3/12
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was NT$20,701, price is now NT$18,548 per person
NT$18,548
per person
Apr 28 - May 1
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (1,016 reviews)
Lots of places to eat and shop nearby
Reviewed on 2026/3/12
L7 Chicago by LOTTE
Downtown Chicago
Price was NT$22,928, price is now NT$20,894 per person
NT$20,894
per person
Apr 28 - May 1
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.6/10 Exceptional! (3,713 reviews)
Excellent location-walkable to many restaurants, theatre, museums, and shopping. The room was very nice and valet parking was a convenient and easy.
Reviewed on 2026/3/13
3 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was NT$21,634, price is now NT$17,955 per person
NT$17,955
per person
Apr 28 - May 1
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 2026/3/9
Hilton Chicago
Downtown Chicago
Price was NT$24,435, price is now NT$20,668 per person
NT$20,668
per person
Apr 28 - May 1
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
It is a very old hotel that is very well maintained.
Room temperature is controlled by maintenance.
Reviewed on 2026/3/12
Top Luxury Illinois Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
The price is NT$11,807 per night from Mar 22 to Mar 23
NT$11,807
NT$13,861 total
Mar 22 - Mar 23
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! (1,848 reviews)
Room was perfect/staff was great
Reviewed on 2026/3/12
The Langham, Chicago
330 North Wabash Avenue Chicago IL
The price is NT$13,835 per night from Apr 5 to Apr 6
NT$13,835
NT$16,241 total
Apr 5 - Apr 6
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 ...
9.8/10 Exceptional! (1,000 reviews)
Room view was awful. Room was average
Reviewed on 2026/3/11
The Peninsula Chicago
108 East Superior Street Chicago IL
The price is NT$16,697 per night from Mar 15 to Mar 16
NT$16,697
NT$19,601 total
Mar 15 - Mar 16
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)
We had everything we needed and more! Great location for shopping and viewing a the beautiful city of Chicago.
Reviewed on 2026/3/13
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.
More Vacation Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
