Oregon Vacations from ￥232,509

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The Latest Oregon Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
This property was right in the heart of downtown and right next to Northwestern - it's a perfect location, and was clean and comfortable!

Reviewed on Aug 11, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
Food options need more variety.

Reviewed on Aug 16, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Oct 9 - Oct 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Amazing view and nice stay! Clean & comfortable! Will come back again!

Reviewed on Aug 16, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on Aug 16, 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
per person
Oct 9 - Oct 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (2,778 reviews)
Excellent hotel in a great location.

Reviewed on Aug 16, 2025

Find the Best Oregon Vacation Packages

Oregon Hotel Deals

Paddle Wheel Inn

Paddle Wheel Inn

2 out of 5
1457 IL Rt 2 North, Oregon, IL
Fully refundableReserve now, pay when you stay
The price is ￥10,620 per night from Aug 25 to Aug 26
￥10,620
￥11,572 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (660 reviews)
"I loved our room with a balcony overlooking the river. Would like to come back to check out restaurants next to the motel."

Reviewed on Aug 10, 2025

Paddle Wheel Inn
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N., Oregon, IL
Fully refundableReserve now, pay when you stay
The price is ￥12,407 per night from Aug 17 to Aug 18
￥12,407
￥14,061 total
Aug 17 - Aug 18
includes taxes & fees
7.8/10 Good! (115 reviews)
"This was very good and clean."

Reviewed on Jul 3, 2025

Chateau Lodge
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

Oregon
9.6/10 Exceptional! (124 reviews)
Wonderful Stay
"we had such a peaceful weekend getaway here! the river views were absolutely stunning — seriously one of the best parts of the stay. the house itself was clean, cozy, and well-stocked, with everything we needed to relax. communication with the owner was super fast and smooth, which made the whole ..."

Reviewed on Jul 14, 2025

Get rates
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
See all 176 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.

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.

Castle Rock State Park

Frequently asked questions

How much does an Oregon vacation package cost?
You can snap up a vacation package to this destination from ￥232,509 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.