Oregon Vacations from ￥270,646
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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥467,216, price is now ￥279,560 per person
￥279,560
per person
May 1 - May 6
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The room was perfect for my birthday weekend my husband planned for me on our business trip turned celebration from Florida. The thoughtfulness and detail of the birthday gestures was so well executed. Kudos to the amazing staff. From being greeted at the door, bellhop service, and the wonderful hospitality team. Beautiful clean hotel and wonderful staff that takes pride in welcoming their guests. Also, you will not be disappointed with the breakfast buffet, they do it right. Thanks Hotel Riu Chicago! Hi Lester! Thanks for chatting with us at breakfast.
Reviewed on Feb 23, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥397,982, price is now ￥292,068 per person
￥292,068
per person
May 1 - May 6
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥495,740, price is now ￥371,432 per person
￥371,432
per person
May 1 - May 6
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
We had a great stay!
Reviewed on Feb 23, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥386,986, price is now ￥293,822 per person
￥293,822
per person
May 1 - May 6
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet
Reviewed on Feb 22, 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 ￥12,954 per night from Feb 24 to Feb 25
￥12,954
￥14,118 total
Feb 24 - Feb 25
includes taxes & fees
8.8/10 Excellent! (695 reviews)
Yes
Reviewed on Feb 16, 2026
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
Oregon IL
9.8/10 Exceptional! (146 reviews)
The host was super accommodating and had great communication. The home had everything we needed and was warm and cozy.
Reviewed on Dec 3, 2025
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
Oregon IL
10/10 Exceptional! (62 reviews)
Amazing cabin with plenty of beds if bringing a large family. Very quiet area. Which i loved
Reviewed on Nov 3, 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 Oregon
Castle Rock State Park
4.5/5(23 reviews)
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.
