Oregon Vacation Packages
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- Plan, book, travel with confidence
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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
Downtown Chicago
CA $1,303
per person
Oct 23 - Oct 30
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Our shower head continually sprayed the bathroom floor. The shower curtain needed to be longer.
Reviewed on Aug 22, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,851
per person
Oct 23 - Oct 30
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Great staff and amenities. Beautiful pool, bbq area and more. Terrific room
Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day
As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them.
For the money your room key or a key pad should allow you in.
Reviewed on Aug 21, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $2,174
per person
Oct 23 - Oct 30
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
I absolutely loved my stay. It was in the perfect location. Walking distance to every site to see. Their customer customer service was great. As well as the in house dining. I definitely will stay here again the next time I visit Chicago
Reviewed on Aug 22, 2026
Ready to book your vacation to Oregon?
Oregon Hotel Deals
Paddle Wheel Inn
1457 IL Rt 2 North Oregon IL
Fully refundableReserve now, pay when you stay
CA $99
CA $108 total
Aug 27 - Aug 28
includes taxes & fees
8.8/10 Excellent! (747 reviews)
"Clean and quiet. The room was basic but worked for us. The only problem was the bathroom door didn't latch! Parking was easy and close. Well worth the cost."
Reviewed on Aug 20, 2026
Chateau Lodge
1326 IL Route 2 N. Oregon IL
Fully refundableReserve now, pay when you stay
CA $88
CA $100 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very good! (154 reviews)
"It was quite and clean."
Reviewed on Aug 12, 2026
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
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.
Lowden State Park
8.8/10 (31 reviews)
You can take time to visit Lowden State Park during your travels to Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.
Conover Square Mall
8.6/10 (16 reviews)
You can do some window-shopping at Conover Square Mall during your trip to Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.
Frequently asked questions
How much does a Oregon vacation package cost?
You'll find cheap prices from CA $1,303 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?
- 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.
- 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.
- 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.
- 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.
