Highwood Vacations from ￥176,152
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Highwood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was ￥218,096, price is now ￥176,152 per person
￥176,152
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,210 reviews)
Lovely hotel! Exceptionally clean and affordable!
Reviewed on Dec 14, 2025
Chicago luxury home suites
Downtown Chicago
Save 100% on your flight
Price was ￥564,895, price is now ￥393,365 per person
￥393,365
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on Nov 26, 2025
La Banque Hotel
Price was ￥243,452, price is now ￥191,074 per person
￥191,074
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.
Reviewed on Nov 30, 2025
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was ￥277,445, price is now ￥222,152 per person
￥222,152
per person
Feb 20 - Feb 25
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (137 reviews)
My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced.
Reviewed on Sep 5, 2025
Find the Best Highwood Vacation Packages
Highwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥31,813 per night from Jan 11 to Jan 12
￥31,813
￥37,347 total
Jan 11 - Jan 12, 2026
includes taxes & fees
8.2/10 Very Good! (2,182 reviews)
right next to the airport. if you stay here here, exit from the front door, take a left and walk to the end of the hotel, and cross the street with a crossing guard, and you are at the airport sliding doors. quick to catch a flight staying here. also, the hotel has a great Jazz bar with live performances. ...
Reviewed on Dec 9, 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥17,084 per night from Dec 18 to Dec 19
￥17,084
￥19,472 total
Dec 18 - Dec 19
includes taxes & fees
8.6/10 Excellent! (2,196 reviews)
Clean
Reviewed on Dec 12, 2025
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is ￥17,139 per night from Dec 19 to Dec 20
￥17,139
￥19,535 total
Dec 19 - Dec 20
includes taxes & fees
8.6/10 Excellent! (2,655 reviews)
Staff was alway polite and helpful, smiles all around, room was clean and everything worked as expected.
Reviewed on Dec 10, 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
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highwood
Wendella's 90-min Chicago River Architecture Tour
￥7,083
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,866
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
