Chicago Luxury Vacations
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Top Luxury vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥473,515, price is now ￥400,650 per person
￥400,650
per person
Nov 30 - Dec 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
Everything about this Hotel was top tier and prestigious. Highly recommended. Rooms were extremely clean, Staff super friendly and the Breakfast was delicious. You have to try the pancakes and French toast
Reviewed on Oct 27, 2025
Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Price was ￥451,932, price is now ￥390,510 per person
￥390,510
per person
Nov 30 - Dec 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,736 reviews)
Clean, quick check in, helpful and speedy valet
Reviewed on Oct 30, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Price was ￥424,685, price is now ￥373,019 per person
￥373,019
per person
Nov 30 - Dec 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,015 reviews)
Rooms are clean. It’s an iconic building in Chicago. It’s also close by many amenities in downtown and loop area.
Reviewed on Oct 29, 2025
5* Luxury vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
3 Night Luxury vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ￥247,973, price is now ￥232,853 per person
￥232,853
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,583 reviews)
We wish they had bidet for the toilet.
Noise from all-day long sirens on the roads , very annoying.
Reviewed on Oct 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥335,652, price is now ￥281,290 per person
￥281,290
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥254,966, price is now ￥236,630 per person
￥236,630
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,994 reviews)
One person at front desk during checkin in the afternoon. Rooms are dates and not well maintained. Bathrooms lights are sunk in, reciept from previous guest shoved in. Toilet paper stuffed in peep hole.
Reviewed on Oct 27, 2025
4 Night Luxury vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was ￥260,574, price is now ￥233,896 per person
￥233,896
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,496 reviews)
Very well located, great bed and shower.
Reviewed on Oct 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
Top Luxury Chicago Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
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! (1,766 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
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
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 Peninsula Chicago
108 East Superior Street, Chicago, IL
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! (1,022 reviews)
Everything was superb. The only “complaint “ I have, is that I paid for a city view room, but actually looked at the side of one building. Other than that, we lived the stay.
Reviewed on Oct 24, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
