Highland Vacations from ￥353,707
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The Latest Highland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Wade
Downtown Chicago
Price was ￥455,390, price is now ￥353,707 per person
￥353,707
per person
Jul 15 - Jul 20
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,834 reviews)
The bathroom door is sliding and does not close completely and the extractor does not work. Excellent location, valet parking somewhat disorganized, staff 3.5/5 of kindness.
Reviewed on May 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥548,170, price is now ￥435,320 per person
￥435,320
per person
Jul 15 - Jul 20
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
Location, cleanliness, overall staff assistance and service and of course breakfast
Reviewed on May 26, 2026
The Emily Hotel
Downtown Chicago
Price was ￥565,608, price is now ￥456,772 per person
￥456,772
per person
Jul 30 - Aug 5
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Great vibes and it’s perfectly located to enjoy the west loop.
Reviewed on May 26, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥444,254, price is now ￥365,090 per person
￥365,090
per person
Jul 15 - Jul 20
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Great hotel. Loved the lobby and our room. Would definitely stay here again.
Reviewed on May 19, 2026
The Langham, Chicago
Downtown Chicago
Price was ￥566,982, price is now ￥473,232 per person
￥473,232
per person
Jul 15 - Jul 20
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
hands down one of the nicest hotels in the city - pool/gym/spa are all amazing. such a good 2nd floor lounge with great views. the staff is all so helpful, friendly
Reviewed on May 26, 2026
Find the Best Highland Vacation Packages
Highland Hotel Deals
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is ￥20,128 per night from Jun 14 to Jun 15
￥20,128
￥22,741 total
Jun 14 - Jun 15
includes taxes & fees
8.6/10 Excellent! (1,061 reviews)
"Always a nice stay."
Reviewed on May 23, 2026
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is ￥26,883 per night from Jun 7 to Jun 8
￥26,883
￥30,105 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (391 reviews)
"The hotel staff was amazing and the bartenders and staff at the Alto Restaurant on the rooftop were also fantastic! The only complaints I have are that the AC did not cool down as well as we would have liked. The lowest we could get it to was 70/71 and it was not comfortable for sleeping. Also, the ..."
Reviewed on May 25, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
The price is ￥25,270 per night from May 27 to May 28
￥25,270
￥29,664 total
May 27 - May 28
includes taxes & fees
6.8/10 (1,002 reviews)
"Nice staff, clean, nice spot. Definitely will stay here the next time I’m in Chicago"
Reviewed on May 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
