Oregon Vacation Packages

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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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,357, price is now CA $849 per person
CA $849
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,883, price is now CA $1,120 per person
CA $1,120
per person
Oct 2 - Oct 7
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,964, price is now CA $1,182 per person
CA $1,182
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,638, price is now CA $1,054 per person
CA $1,054
per person
Nov 10 - Nov 17
found 18 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug. 26, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,450, price is now CA $934 per person
CA $934
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

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 $99 per night from Sep 1 to Sep 2
CA $99
CA $108 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (663 reviews)
"Beautiful view of the river."

Reviewed on Aug. 22, 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 CA $116 per night from Aug 31 to Sep 1
CA $116
CA $132 total
Aug 31 - Sep 1
includes taxes & fees
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)
"Had fun time with my family fishing place was very clean and inviting"

Reviewed on Aug. 10, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Oregon vacation package cost?
You'll find cheap prices from CA $849 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.