
Oregon Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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
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



theWit Chicago, a Hilton Hotel
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
Oregon Hotel Deals

Paddle Wheel Inn
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

Chateau Lodge
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

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
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.
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.