Highland Vacations from ₩1,569,114
Book a 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*
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The Latest Highland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ₩2,144,860, price is now ₩1,569,114 per person
₩1,569,114
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,912,014, price is now ₩1,792,229 per person
₩1,792,229
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Loved my stay her staff was very hospitable and met all our needs. The breakfast buffet was the best I have ever been to.
Reviewed on Mar 9, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩3,689,584, price is now ₩2,680,320 per person
₩2,680,320
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.
Reviewed on Mar 3, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ₩2,281,394, price is now ₩1,726,360 per person
₩1,726,360
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.
Reviewed on Mar 9, 2026
Arlo Chicago
Downtown Chicago
Price was ₩2,545,408, price is now ₩2,015,210 per person
₩2,015,210
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,993 reviews)
Very clean, small but beautiful updated rooms. Great location. Would stay again. Discounted parking close by.
Reviewed on Mar 9, 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 ₩150,845 per night from Mar 29 to Mar 30
₩150,845
₩170,423 total
Mar 29 - Mar 30
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
N/A
Reviewed on Mar 9, 2026
Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Fully refundableReserve now, pay when you stay
The price is ₩169,093 per night from Mar 16 to Mar 17
₩169,093
₩194,423 total
Mar 16 - Mar 17
includes taxes & fees
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is ₩225,719 per night from Mar 10 to Mar 11
₩225,719
₩252,764 total
Mar 10 - Mar 11
includes taxes & fees
9.4/10 Exceptional! (278 reviews)
Very clean inside and out.
Reviewed on Mar 7, 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.
