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 Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
Price was ￥314,496, price is now ￥279,953 per person
￥279,953
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (1,226 reviews)
Great hotel at an affordable price
Reviewed on Jan 26, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥335,237, price is now ￥287,732 per person
￥287,732
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Clean shopping near by
Reviewed on Jan 18, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥546,483, price is now ￥469,544 per person
￥469,544
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥393,092, price is now ￥353,387 per person
￥353,387
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Excellent stay. The hotel is beautifully designed, with a perfect blend of historic character and modern comfort. The room was spotless, quiet, and very comfortable, with great attention to detail.
What really stood out was the staff — warm, professional, and genuinely helpful from check-in to check-out. The location is also ideal, close to everything yet calm and relaxing after a long day.
Reviewed on Jan 29, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥390,266, price is now ￥351,506 per person
￥351,506
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on Jan 23, 2026
5* Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥416,804, price is now ￥376,541 per person
￥376,541
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Room was great and staff very attebtive and kind
Reviewed on Jan 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥546,483, price is now ￥469,544 per person
￥469,544
per person
Apr 7 - Apr 13
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
3 Night Luxury vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥327,716, price is now ￥277,202 per person
￥277,202
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,208 reviews)
We got an upgrade to a king suite. Everything was fantastic
Reviewed on Jan 29, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥412,774, price is now ￥338,176 per person
￥338,176
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥344,189, price is now ￥289,346 per person
￥289,346
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on Jan 23, 2026
Top Luxury Illinois Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
The price is ￥45,562 per night from Feb 8 to Feb 9
￥45,562
￥53,486 total
Feb 8 - Feb 9
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! (1,827 reviews)
The room and the staff were wonderful!
Reviewed on Jan 22, 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
The price is ￥59,958 per night from Mar 1 to Mar 2
￥59,958
￥70,385 total
Mar 1 - Mar 2
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! (1,008 reviews)
Staff was wonderful.
Reviewed on Jan 25, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
The price is ￥72,742 per night from Feb 1 to Feb 2
￥72,742
￥85,393 total
Feb 1 - Feb 2
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 ...
9.6/10 Exceptional! (1,011 reviews)
Amazing staff. Sooooo clean. Top service
Reviewed on Jan 25, 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.
