Oregon Vacations from ￥313,997
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 Oregon Vacation Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
Price was ￥373,915, price is now ￥313,997 per person
￥313,997
per person
Feb 20 - Feb 23
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
The room was clean. Staff and bar was really nice.
Reviewed on Dec 18, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥471,930, price is now ￥365,182 per person
￥365,182
per person
Feb 20 - Feb 23
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Chicago Marriott Suites O'Hare
Price was ￥384,612, price is now ￥321,928 per person
￥321,928
per person
Feb 20 - Feb 23
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The staff were friendly and professional. The room was clean and as expected. Only drawback was the lack of amenities. Coffee was out of a machine in lobby and cost $4 - WiFi was not free and $15 a day.
Reviewed on Dec 28, 2025
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was ￥394,990, price is now ￥331,453 per person
￥331,453
per person
Feb 20 - Feb 23
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (2,558 reviews)
Elevators were ridiculously slow and full. Had to wait 10+ minutes to get on one.
Reviewed on Jan 6, 2026
Sonesta Chicago O'Hare Airport Rosemont
Price was ￥379,972, price is now ￥319,051 per person
￥319,051
per person
Feb 20 - Feb 23
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.6/10 Excellent! (1,633 reviews)
Very quiet considering proximity to the airport
Reviewed on Jan 7, 2026
Find the Best Oregon Vacation Packages
Oregon Hotel Deals
Paddle Wheel Inn
1457 IL Rt 2 North Oregon IL
Fully refundableReserve now, pay when you stay
The price is ￥13,085 per night from Jan 9 to Jan 10
￥13,085
￥14,261 total
Jan 9 - Jan 10
includes taxes & fees
8.6/10 Excellent! (686 reviews)
Very nice staff and room was nice and clean as well.
Reviewed on Jan 2, 2026
Chateau Lodge
1326 IL Route 2 N. Oregon IL
8/10 Very Good! (132 reviews)
Clean room
Reviewed on Dec 13, 2025
WHOLE ISLAND TO YOURSELF, boat included. Sleeps 8 people.
Oregon IL
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 Oregon
Castle Rock State Park
You can take time to visit Castle Rock State Park during your travels to Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.
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.
