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
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul. 21, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Accessibility to Wendella Tours, shopping and the ‘L’ to go sightseeing

Reviewed on Jul. 24, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
The hotel was fine. But between the bed being the hardest bed ever and the music from the roof top club we didn't get much sleep.

Reviewed on Jul. 23, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Close proximity to everything

Reviewed on Jul. 22, 2025

Ready to book your vacation to Oregon?

 

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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 $98 per night from Jul 28 to Jul 29
CA $98
CA $107 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (651 reviews)
"Overall it's not a bad place. We got in early and the staff let us check in. We needed to get ready for a wedding so that was really helpful. The air unit was a little noisy, but everything else was fine."

Reviewed on Jul. 9, 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 $121 per night from Aug 7 to Aug 8
CA $121
CA $137 total
Aug 7 - Aug 8
includes taxes & fees
7.8/10 Good! (115 reviews)
"This was very good and clean."

Reviewed on Jul. 3, 2025

Chateau Lodge
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Oregon
9.8/10 Exceptional! (53 reviews)
Hidden Gem
"If you are looking for the perfect spot for your group of 6-8, this is it! The wrap around deck, fire pit and outdoor grilling station are just part of why it is perfect. The indoor kitchen is perfect for a group cooking and serving. We had a great thunderstorm roll through and watched it from the ..."

Reviewed on Jul. 20, 2025

Get rates
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
See all 175 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

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Frequently asked questions

How much does a Oregon vacation package cost?
You'll find cheap prices from CA $619 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.