Highland Park Vacations from ￥358,974
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The Latest Highland Park Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥540,466, price is now ￥358,974 per person
￥358,974
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
St
Add very friendly, clean and great breakfast
Reviewed on Feb 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥647,042, price is now ￥463,177 per person
￥463,177
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
We had a great stay!
Reviewed on Feb 23, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥531,588, price is now ￥383,018 per person
￥383,018
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
From beginning to the end my stay was a 10/10. I only stayed one night but that one night was worth it.
Reviewed on Feb 24, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥576,142, price is now ￥415,219 per person
￥415,219
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Clean room, great staff.
Reviewed on Feb 25, 2026
Virgin Hotels Chicago
Downtown Chicago
Price was ￥538,122, price is now ￥391,416 per person
￥391,416
per person
Apr 14 - Apr 19
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Room was very clean, staff was very pleasant. Will definitely return
Reviewed on Feb 15, 2026
Find the Best Highland Park Vacation Packages
Highland Park Hotel Deals
Holiday Inn Chicago North-Evanston by IHG
1501 Sherman Ave Evanston IL
Fully refundable
The price is ￥13,485 per night from Mar 2 to Mar 3
￥13,485
￥15,438 total
Mar 2 - Mar 3
includes taxes & fees
8.6/10 Excellent! (1,799 reviews)
Reasonably priced, clean room, great service.
Reviewed on Feb 25, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,306 per night from Mar 20 to Mar 21
￥30,306
￥35,577 total
Mar 20 - Mar 21
includes taxes & fees
8.4/10 Very Good! (2,238 reviews)
Great staff
Reviewed on Feb 24, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,169 per night from Mar 16 to Mar 17
￥16,169
￥18,981 total
Mar 16 - Mar 17
includes taxes & fees
8.2/10 Very Good! (1,288 reviews)
Great location!
Reviewed on Feb 24, 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.
Discover the most popular places to visit in Highland Park
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highland Park
Chicago River: 1.5-Hour Guided Architecture Cruise
￥6,810
per adult
98% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
￥6,269
per adult
94% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
