Oregon Vacations from ¥275,330

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    Save up to ¥109,000 when you book a flight and hotel together*
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The Latest Oregon Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago
¥275,330
per person
Oct 3 - Oct 6
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,775 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,235
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥309,912
per person
Oct 3 - Oct 6
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Love the place

Reviewed on Aug 30, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥285,588
per person
Oct 3 - Oct 6
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Beautiful view

Reviewed on Aug 30, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥305,031
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (159 reviews)

Find the Best Oregon Vacation Packages

Oregon Hotel Deals

Paddle Wheel Inn

Paddle Wheel Inn

1457 IL Rt 2 North Oregon IL
Fully refundableReserve now, pay when you stay
¥11,550
¥12,586 total
Aug 31 - Sep 1
includes taxes & fees
Paddle Wheel Inn
Chateau Lodge

Chateau Lodge

1326 IL Route 2 N. Oregon IL
Fully refundableReserve now, pay when you stay
¥11,017
¥12,486 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (158 reviews)
"The stay was really good, cute room and clean"

Reviewed on Aug 28, 2026

Chateau Lodge
ROCK RIVER HIDEAWAY

ROCK RIVER HIDEAWAY

Oregon IL
ROCK RIVER HIDEAWAY
See all 195 properties in Oregon
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.

Stay near popular Oregon attractions

Castle Rock State Park

8.8/10 (55 reviews)
Perched atop a sandstone bluff, Castle Rock State Park offers panoramic views of the Rock River and rolling hills. Hike the scenic trails in autumn to witness a breathtaking display of vibrant foliage.
See properties

Lowden State Park

8.8/10 (31 reviews)
Gaze up at the towering 48-foot Eternal Indian statue overlooking Rock River's scenic bluffs. Hike through hardwood forests or reserve a campsite to fully experience this tranquil Illinois retreat.
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Conover Square Mall

8.6/10 (16 reviews)
Once a piano factory, this historic mall houses specialty shops, antiques, and a model railroad exhibit. Wander through its charming maze of hallways to discover handcrafted treasures and nostalgic architectural details.
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Frequently asked questions

How much does an Oregon vacation package cost?
You can snap up a vacation package to this destination from ¥275,330 on Expedia. However, how much your vacation to Oregon costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Oregon?
December, January and February are great times to search for cheap Oregon vacation packages. Choosing to travel in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Oregon?
The ideal length of your Oregon vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you time to check out all the main sights and explore some hidden spots along the way.
Is it worth booking a vacation package to Oregon?
During your Oregon vacation, you can count on experiencing some excellent nature and culture. Leave enough time in your itinerary to discover major sights like Castle Rock State Park and Lowden State Park.
How to find the best Oregon package deals?
Use Expedia's filters to find some tempting Oregon package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Oregon package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Oregon vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Oregon vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Oregon?
If you're considering a spontaneous Oregon trip, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Oregon?
  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Oregon.
  2. Set a budget: Factor in costs like transportation, flights and meals when working out how much to put aside for your trip to Oregon. Then, choose a hotel that matches your budget, whether that's an affordable stay or a more luxurious retreat.
  3. Decide how long to go away for: Now that you're up to speed on Oregon, you can work out the ideal length of your vacation. Create a rough plan and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: Once you've settled on your travel dates and duration, book the perfect Oregon vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.