
Pearl City Vacations from ¥368,190
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The Latest Pearl City Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Price was ¥495,657, price is now ¥368,190 per person
¥368,190
per person
May 28 - Jun 2
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (414 reviews)
This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back.
Reviewed on Mar 8, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥640,345, price is now ¥417,190 per person
¥417,190
per person
May 28 - Jun 2
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.
Reviewed on Mar 9, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥624,805, price is now ¥463,414 per person
¥463,414
per person
May 28 - Jun 2
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Every thing was amazing the staff was friendly and helpful shops and everything was close by I loved it thank you again
Reviewed on Mar 9, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥653,618, price is now ¥488,172 per person
¥488,172
per person
May 28 - Jun 2
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.
Reviewed on Mar 3, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥573,854, price is now ¥430,932 per person
¥430,932
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.
Reviewed on Mar 9, 2026
Find the Best Pearl City Vacation Packages
Pearl City Hotel Deals

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Pearl City IL
The price is ¥11,608 per night from Mar 11 to Mar 12
¥11,608
¥45,916 total
Mar 11 - Mar 12
includes taxes & fees

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is ¥15,920 per night from Mar 29 to Mar 30
¥15,920
¥17,668 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (869 reviews)
Clean rooms, comfortable bed, good breakfast on the morning. Great location with plenty of dining options close by.
Reviewed on Mar 2, 2026

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake
Apple River IL
9.8/10 Exceptional! (226 reviews)
Cabin was beautiful and the perfect getaway for our family ski trip at Chestnut Mountain. Comfortable beds and linens, hosts were very hospitable, and kitchen was well-stocked.
Reviewed on Feb 15, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
