Pearl City Vacations from ￥185,789
Book a Hotel + Flight or Car together to unlock savings
- 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
- Rest easyPlan, book, and manage your trip all in one place
The Latest Pearl City Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥221,032, price is now ￥185,789 per person
￥185,789
per person
Mar 4 - Mar 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.
Reviewed on Jan 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,704, price is now ￥319,797 per person
￥319,797
per person
Mar 15 - Mar 19
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥337,890, price is now ￥285,200 per person
￥285,200
per person
Mar 15 - Mar 19
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 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 ￥12,105 per night from Jan 26 to Jan 27
￥12,105
￥46,720 total
Jan 26 - Jan 27
includes taxes & fees
10/10 Exceptional! (3 reviews)
Best stay
Out of half a dozen or so cabin rentals, this one is the absolute best. It's clean, uncluttered, quiet, and huge! Water was hot, heater worked really well (it was a very cold week) and the kitchen worked well. Beds were comfy too. I can't say enough good things about this place!
Reviewed on Dec 5, 2024
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is ￥16,001 per night from Feb 6 to Feb 7
￥16,001
￥17,758 total
Feb 6 - Feb 7
includes taxes & fees
8.8/10 Excellent! (857 reviews)
Clean staff very courteous
Reviewed on Jan 13, 2026
Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is ￥16,458 per night from Feb 6 to Feb 7
￥16,458
￥18,265 total
Feb 6 - Feb 7
includes taxes & fees
8.6/10 Excellent! (452 reviews)
pool was nice, friendly staff,
Reviewed on Dec 29, 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.
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.
