Illinois Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Luxury vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was ₩4,090,718, price is now ₩3,330,864 per person
₩3,330,864
per person
Jun 12 - Jun 17
found 1 hour ago
Roundtrip non-stop flight included
Honolulu (HNL) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
We were very pleased with The Gwen. Would definitely recommend!
Reviewed on Apr 17, 2026
L7 Chicago by LOTTE
Downtown Chicago
Price was ₩3,238,228, price is now ₩2,684,409 per person
₩2,684,409
per person
Jun 12 - Jun 17
found 1 hour ago
Roundtrip non-stop flight included
Honolulu (HNL) to Chicago (ORD)
9.6/10 Exceptional! (3,910 reviews)
Great location, lovely front desk staff and a fun popcorn and drinks situation in the early evening. The staff knew it was my son’s 18th birthday and also that we were in town for a college visit, and they surprised us with the sweetest note with cupcakes and balloons in our room. Above and beyond! Walkable to Millenium Park and centrally located downtown. Would absolutely stay again!
Reviewed on Apr 20, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ₩2,986,475, price is now ₩2,499,507 per person
₩2,499,507
per person
Jun 12 - Jun 17
found 1 hour ago
Roundtrip non-stop flight included
Honolulu (HNL) to Chicago (ORD)
9.4/10 Exceptional! (1,047 reviews)
Wonderful restaurant, amazing food.
Reviewed on Apr 18, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ₩3,127,111, price is now ₩2,634,636 per person
₩2,634,636
per person
Jun 12 - Jun 17
found 1 hour ago
Roundtrip non-stop flight included
Honolulu (HNL) to Chicago (ORD)
8.8/10 Excellent! (2,168 reviews)
One elevator was down the whole time we were there. So there was only one elevator working. Water pressure in the shower was terrible. Overall just an okay hotel
Reviewed on Apr 18, 2026
Top Luxury Illinois Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
The price is ₩684,506 per night from Apr 27 to Apr 28
₩684,506
₩803,592 total
Apr 27 - Apr 28
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! (1,853 reviews)
Great
Reviewed on Apr 19, 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
The price is ₩794,027 per night from May 21 to May 22
₩794,027
₩944,075 total
May 21 - May 22
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! (1,005 reviews)
.
Reviewed on Apr 20, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
The price is ₩766,647 per night from Apr 26 to Apr 27
₩766,647
₩900,022 total
Apr 26 - Apr 27
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! (1,007 reviews)
Great
Reviewed on Apr 20, 2026
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.
