Highland Park Vacations from ￥256,077
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- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Highland Park Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was ￥328,545, price is now ￥256,077 per person
￥256,077
per person
Dec 31 - Jan 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.
Reviewed on Nov 18, 2025
The Emily Hotel
Downtown Chicago
Price was ￥434,324, price is now ￥312,520 per person
￥312,520
per person
Dec 31 - Jan 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special
Reviewed on Nov 11, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥400,331, price is now ￥297,527 per person
￥297,527
per person
Dec 31 - Jan 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥344,924, price is now ￥268,894 per person
￥268,894
per person
Dec 31 - Jan 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
17.6/10 Exceptional! (3,098 reviews)
Yes, yes, and yes, everything was wonderful
Reviewed on Nov 18, 2025
Find the Best Highland Park Vacation Packages
Highland Park Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,481 per night from Dec 12 to Dec 13
￥30,481
￥35,782 total
Dec 12 - Dec 13
includes taxes & fees
8.2/10 Very Good! (2,166 reviews)
Clean and great service.
Reviewed on Nov 19, 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥21,619 per night from Nov 25 to Nov 26
￥21,619
￥24,641 total
Nov 25 - Nov 26
includes taxes & fees
8.6/10 Excellent! (2,128 reviews)
Friendly staff. Quick check-in
Reviewed on Nov 17, 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 ￥13,901 per night from Nov 26 to Nov 27
￥13,901
￥15,427 total
Nov 26 - Nov 27
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Awesome stay and amazing customer service
Reviewed on Nov 14, 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 Highland Park
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 Highland Park
Skydeck - Willis Tower Admission
￥6,717
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,749
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.
