Oregon Vacations from ￥295,012

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The Latest Oregon Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Price was ￥337,531, price is now ￥295,012 per person
￥295,012
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
There was a hair ball on the side of the toilet and a couple spiders came in the window the staff was bland with no reactions.

Reviewed on Jul 12, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥379,612, price is now ￥309,040 per person
￥309,040
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
My husband and I thoroughly enjoyed our stay at Londonhouse! It’s in a perfect location and walking distance to many CTA bus stops, which helped immensely with us being able to get around! Despite being in a heavy traffic area, there were no noise disturbances. The room and bathroom were super clean as well! Will definitely be staying here the next time we are in Chicago!

Reviewed on Jul 12, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was ￥366,988, price is now ￥312,042 per person
￥312,042
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,123 reviews)
Good value.

Reviewed on Jul 11, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was ￥370,063, price is now ￥321,758 per person
￥321,758
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,429 reviews)
Clean rooms and friendly staff!

Reviewed on Jul 12, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥348,343, price is now ￥305,115 per person
￥305,115
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,879 reviews)
Room was clean, with great city views. Long waits for elevator with lines due to multiple events happening. Otherwise, no complaints

Reviewed on Jul 12, 2026

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 ￥13,508 per night from Jul 19 to Jul 20
￥13,508
￥14,722 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (730 reviews)
"We stayed in a very small room with a double bed, and it was perfect! Price was very reasonable and staff was tremendous! Beautiful patio area overlooking the Rock River where we enjoyed morning coffee and watched the eagles overhead, friendly guests that chatted with us. All in all, a GREAT place ..."

Reviewed on Jul 11, 2026

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 ￥11,127 per night from Jul 26 to Jul 27
￥11,127
￥12,611 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very Good! (149 reviews)
"If you check in early they charge 40 dollars don't go here go t o the paddelwheel"

Reviewed on Jul 7, 2026

Chateau Lodge
ROCK RIVER HIDEAWAY

ROCK RIVER HIDEAWAY

Oregon IL
9.8/10 Exceptional! (154 reviews)
"Everything was exactly as described and we enjoyed a pleasant stay. We were able to fish right off the deck."

Reviewed on Jul 8, 2026

Get rates
ROCK RIVER HIDEAWAY
See all 192 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

Frequently asked questions

How much does an Oregon vacation package cost?
You can snap up a vacation package to this destination from ￥295,012 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.

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.