Oregon Vacations from ￥340,688

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The Latest Oregon Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥413,758, price is now ￥340,688 per person
￥340,688
per person
Aug 25 - Aug 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
The staff was very friendly while providing excellent customer service. Our room and hotel were well maintained and clean. The daily breakfast and coffee provided was also very delicious

Reviewed on Jul 15, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥520,328, price is now ￥420,151 per person
￥420,151
per person
Aug 25 - Aug 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Overall very satisfied with the service. Location is top notch. Just a stone throw away from lots of activities.

Reviewed on Jul 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥516,279, price is now ￥430,770 per person
￥430,770
per person
Aug 25 - Aug 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on Jul 14, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥457,188, price is now ￥381,469 per person
￥381,469
per person
Aug 25 - Aug 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥438,092, price is now ￥373,984 per person
￥373,984
per person
Aug 25 - Aug 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Holes in the carpeting in living room. Door that enters unit doesn’t close without slamming it. Looks like wear and tear since we were there before.

Reviewed on Jul 14, 2026

Find the Best Oregon Vacation Packages

Oregon Hotel Deals

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

2.5 out of 5
1120 Park Street Oregon WI
Fully refundable
The price is ￥12,899 per night from Aug 12 to Aug 13
￥12,899
￥14,641 total
Aug 12 - Aug 13
includes taxes & fees
9.4/10 Exceptional! (438 reviews)
"Everything was quite good, especially considering the price. However, there were a couple of guys getting ice from the ice machine in the middle of the night, and it was incredibly loud for quite a long period of time. It was around 4–5 a.m. I was curious about what could be making such a huge noise ..."

Reviewed on Jul 14, 2026

Sleep Inn & Suites Oregon - Madison
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is ￥23,444 per night from Aug 2 to Aug 3
￥23,444
￥27,078 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (3,975 reviews)
"Great pool area"

Reviewed on Jul 15, 2026

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is ￥11,389 per night from Aug 4 to Aug 5
￥11,389
￥13,154 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very Good! (1,369 reviews)
"The walls are paper, thin, and you can hear everything. Which means they can hear everything. The people in the first room were extremely loud. The staff helped me move to a different room. That room was no better where the neighbors were just as loud at 2:00 AM. The Wi-Fi did not work. I was able ..."

Reviewed on Jul 15, 2026

Baymont by Wyndham Madison West/Middleton WI West
See all 496 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

Legend at Bergamont

Designed by two-time U.S. Open Champion Andy North, this championship course earned Golf Digest's "Top 10 New Courses" honor. Visitors enjoy resort amenities including pool, tennis, and panoramic clubhouse views.
See properties

Frequently asked questions

How much does an Oregon vacation package cost?
You'll find cheap prices from ￥340,688 on Expedia for your Oregon break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oregon costs.
What are the cheapest months to go to Oregon?
If you're hoping to score a cheap Oregon vacation package, consider traveling in January, July and November. You're likely to find lower prices on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Oregon?
The ideal duration for your Oregon vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to hit all the leading sights and discover some hidden treasures along the way.
How to find the best Oregon package deals?
Bagging a cheap Oregon package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oregon package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Oregon vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Oregon vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Oregon?
If you're considering an impromptu Oregon vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Oregon?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Oregon.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Oregon.
  3. Decide how long to go for: Now that you know more about Oregon, you can figure out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose an Oregon vacation package that brings all your bookings together.

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.