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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,134, price is now CA $821 per person
CA $821
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,039, price is now CA $1,462 per person
CA $1,462
per person
Dec 9 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,315 per person
CA $1,315
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,001, price is now CA $2,200 per person
CA $2,200
per person
Dec 16 - Dec 21
just found
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Very good service

Reviewed on Nov 9, 2026

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 $109 per night from Nov 10 to Nov 11
CA $109
CA $118 total
Nov 10 - Nov 11
includes taxes & fees
8.8/10 Excellent! (764 reviews)
"I took a river view room and it was fantastic. I didn't give a 5 star because, in early November with extreme low the occupancy, the hotel probably could not afford to offer service. There was no hot coffee in the morning and no staff around. I don't blame them though."

Reviewed on Nov 8, 2026

Paddle Wheel Inn
ROCK RIVER HIDEAWAY

ROCK RIVER HIDEAWAY

Oregon IL
9.6/10 Exceptional! (164 reviews)
"Great place on the river..as advertised. Would stay again."

Reviewed on Oct 27, 2026

Get rates
ROCK RIVER HIDEAWAY
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 CA $92 per night from Nov 11 to Nov 12
CA $92
CA $104 total
Nov 11 - Nov 12
includes taxes & fees
8/10 Very good! (166 reviews)
"Dead bugs in the shower, the photos of rooms must be A.I. enhanced as they looked decent online but dingy and sketchy in person. We wound up not staying the night and booked accommodations elsewhere. Staff were in the office when we arrived, but they keep the door locked. So we felt it may not be ..."

Reviewed on Nov 8, 2026

Chateau Lodge
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 $821 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.