Highwood Vacations from ￥89,632
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Save 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥150,367, price is now ￥96,985 per person
￥96,985
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Our stay was absolutely excellent! The room was spotless and stylish, but what really stood out was the rooftop — breathtaking views, great ambiance, and the perfect spot to unwind. The concierge team was phenomenal — attentive, knowledgeable, and made every recommendation feel personalized. From check-in to check-out, everything felt seamless and top-tier. Truly a 5-star experience worth repeating!
Reviewed on Oct 28, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,720, price is now ￥300,282 per person
￥300,282
per person
Dec 7 - Dec 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home.
Reviewed on Oct 26, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥119,932, price is now ￥97,155 per person
￥97,155
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Easy check-in, friendly staff, beautiful building with nice amenities.
Reviewed on Oct 27, 2025
The Emily Hotel
Downtown Chicago
Price was ￥120,398, price is now ￥98,470 per person
￥98,470
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Excellent stay. The hotel staff is very courteous and helpful, and the location is great!
Reviewed on Oct 28, 2025
Find the Best Highwood Vacation Packages
Highwood Hotel Deals
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 ￥13,401 per night from Nov 9 to Nov 10
￥13,401
￥14,874 total
Nov 9 - Nov 10
includes taxes & fees
8/10 Very Good! (1,068 reviews)
Cooperative staff at front desk
Reviewed on Oct 27, 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2, Rosemont, IL
Fully refundable
The price is ￥16,130 per night from Nov 27 to Nov 28
￥16,130
￥18,650 total
Nov 27 - Nov 28
includes taxes & fees
8.8/10 Excellent! (2,515 reviews)
Got stuck in Chicago so needed a place to stay. The staff was friendly, they offer a free shuttle service, have a large restaurant on site, and everything was clean. Would recommend!
Reviewed on Oct 27, 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is ￥17,956 per night from Nov 26 to Nov 27
￥17,956
￥20,466 total
Nov 26 - Nov 27
includes taxes & fees
8.6/10 Excellent! (2,106 reviews)
I give the hotel 10 out 10, I enjoyed the stay & the breakfast was really good. I enjoyed it!
Reviewed on Oct 27, 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
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.
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.
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
Skydeck - Willis Tower Admission
￥6,612
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,691
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.
