Highwood Vacations from ₩589,714
Book a Hotel + Flight or Car together to unlock savings
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- Plan, book, travel with confidence
Better together
Save up to ₩234,741 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Highwood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was ₩961,022, price is now ₩589,714 per person
₩589,714
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on Oct 4, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,747,949, price is now ₩1,040,990 per person
₩1,040,990
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on Oct 6, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,623,004, price is now ₩983,945 per person
₩983,945
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.
Reviewed on Oct 10, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,012,408, price is now ₩625,567 per person
₩625,567
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on Oct 7, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,495,140, price is now ₩1,584,500 per person
₩1,584,500
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
We have stayed at every luxury property in Chicago and when coming to visit we always stay at the Park Hyatt. The rooms are spectacular!
Reviewed on Oct 10, 2025
Find the Best Highwood Vacation Packages
Highwood Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
The price is ₩205,415 per night from Oct 26 to Oct 27
₩205,415
₩234,133 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (2,048 reviews)
"a bit dated but great for catching an early morning fligjt"
Reviewed on Oct 9, 2025
Marriott Chicago O'Hare
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩217,041 per night from Oct 24 to Oct 25
₩217,041
₩254,783 total
Oct 24 - Oct 25
includes taxes & fees
8.4/10 Very Good! (1,161 reviews)
"The staff and service is wonderful! Room service food is delicious and always quick delivery."
Reviewed on Oct 8, 2025
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is ₩139,197 per night from Oct 19 to Oct 20
₩139,197
₩154,481 total
Oct 19 - Oct 20
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"I can’t complain. I was only there one night but the place was really clean and spacious for what I paid."
Reviewed on Oct 4, 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.
Discover the most popular places to visit in Highwood
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Grant Park
4.5/5(3,318 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
