Oregon Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Your Oregon Vacation

Uncover the very best of Oregon with a customized Oregon vacation package. From its lively atmosphere and progressive thinking to its spectacular views, you'll love getting to know this coastal city in your own way. Castle Rock State Park, Lowden State Park and Conover Square Mall are just a few of the many sights worth exploring during your trip to Oregon. No matter your travel plans or budget, organizing a tailored Oregon vacation is simple with Expedia.

Top Oregon Vacation Deals

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 CA $1,164, price is now CA $795 per person
CA $795
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,858 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,642, price is now CA $1,029 per person
CA $1,029
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
It was lovely!!

Reviewed on Jul 29, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,678, price is now CA $1,168 per person
CA $1,168
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)
Comes with all the comforts of Home.

Reviewed on Jul 29, 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 CA $1,496, price is now CA $1,077 per person
CA $1,077
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Under construction, had to take the stairs for 4days, got my steps in :)

Reviewed on Jul 29, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,722, price is now CA $1,276 per person
CA $1,276
per person
Sep 25 - Sep 28
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,502 reviews)

Ready to book your vacation to Oregon?

 

Choose your dates

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 CA $102 per night from Aug 3 to Aug 4
CA $102
CA $111 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (738 reviews)
"n/a"

Reviewed on Jul 27, 2026

Paddle Wheel Inn
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N. Oregon IL
The price is CA $97 per night from Aug 12 to Aug 13
CA $97
CA $110 total
Aug 12 - Aug 13
includes taxes & fees
8.2/10 Very good! (152 reviews)
"If you’re looking for comfortable and affordable me lodging in the Oregon area, this is a great choice. The property and rooms are adorable and simple. Room meets your basic needs for visiting the area to enjoy the state parks and nature. This was a great value. Easy and short drive to all the parks ..."

Reviewed on Jul 26, 2026

Chateau Lodge
ROCK RIVER HIDEAWAY

ROCK RIVER HIDEAWAY

Oregon IL
9.8/10 Exceptional! (156 reviews)
"//"

Reviewed on Jul 21, 2026

Get rates
ROCK RIVER HIDEAWAY
See all 191 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.
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Stay near popular Oregon attractions

Castle Rock State Park

8.8/10 (55 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.
See properties

Frequently asked questions

How much does a Oregon vacation package cost?
You'll find cheap prices from CA $795 on Expedia for your Oregon escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Oregon costs.
What are the cheapest months to go to Oregon?
You can generally find lower prices and greater availability in December, January and February. Check out our cheap Oregon vacation packages and you could score some great off-season deals.
How many days is enough for Oregon?
The ideal length for your Oregon vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to hit all the major attractions and explore some hidden treasures along the way.
Is it worth booking a vacation package to Oregon?
Whether you're planning to explore attractions such as Castle Rock State Park and Lowden State Park, or want to experience its top-notch nature and culture, a Oregon vacation is sure to exceed your expectations. Book your getaway with Expedia and discover why Oregon is such a good vacation destination.
How to find the best Oregon package deals?
Finding a cheap Oregon package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most affordable Oregon package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Oregon vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations individually. Better still, you can tailor your Oregon escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oregon?
If you're considering a spontaneous Oregon adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Oregon?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Oregon.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will likely be the largest expense during your trip to Oregon.
  3. Decide how long to go away 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 to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Oregon vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.