Illinois Luxury Vacations
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Top Luxury vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥533,920, price is now ￥419,258 per person
￥419,258
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!
Reviewed on Mar 17, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥681,242, price is now ￥515,418 per person
￥515,418
per person
May 28 - Jun 2
found 18 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥547,652, price is now ￥442,049 per person
￥442,049
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans!
The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too!
The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well!
All and all it’s a wonderful place to experience!!!!🍍
Reviewed on Mar 18, 2026
5* Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥681,242, price is now ￥515,418 per person
￥515,418
per person
May 28 - Jun 2
found 18 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥638,444, price is now ￥613,331 per person
￥613,331
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful! Enjoyed a relaxing weekend.
Reviewed on Mar 18, 2026
3 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥436,672, price is now ￥395,214 per person
￥395,214
per person
Jun 7 - Jun 10
found 17 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans!
The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too!
The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well!
All and all it’s a wonderful place to experience!!!!🍍
Reviewed on Mar 18, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥448,707, price is now ￥397,403 per person
￥397,403
per person
Jun 7 - Jun 10
found 17 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
L7 Chicago by LOTTE
Downtown Chicago
Price was ￥459,184, price is now ￥419,918 per person
￥419,918
per person
Jun 7 - Jun 10
found 17 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (3,749 reviews)
Booked deluxe river view, but it was really a partial view from the side
Reviewed on Mar 16, 2026
4 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥398,086, price is now ￥332,476 per person
￥332,476
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!
Reviewed on Mar 17, 2026
Top Luxury Illinois Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
The price is ￥59,018 per night from Mar 25 to Mar 26
￥59,018
￥69,281 total
Mar 25 - Mar 26
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! (1,847 reviews)
Excellent
Reviewed on Mar 17, 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
The price is ￥71,537 per night from Apr 5 to Apr 6
￥71,537
￥83,975 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! (1,002 reviews)
yes
Reviewed on Mar 16, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
The price is ￥83,459 per night from Mar 23 to Mar 24
￥83,459
￥97,972 total
Mar 23 - Mar 24
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! (1,009 reviews)
Excellent in every way!
Reviewed on Mar 17, 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.
