Title: Oregon Vacation Packages & Trips 2026 from CA $829 | Expedia.ca [Hotels in Oregon](https://expedia.ca/Oregon-Hotels.d55882.Travel-Guide-Hotels)[Vacation Rentals in Oregon](https://expedia.ca/Oregon-Vacation-Rentals.d55882.Travel-Guide-VacationRentals)[Flights to Oregon](https://expedia.ca/Cheap-Flights-To-Oregon.d55882.Travel-Guide-Flights)[Oregon Car Rentals](https://expedia.ca/Car-Rentals-In-Oregon.d55882.Car-Rental-Guide) ![](https://images.trvl-media.com/place/55882/105b471e-875e-4b18-9a19-bab66db39bf8.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # 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](https://www.expedia.ca/Castle-Rock-State-Park-Illinois.d553248621532658449.Vacation-Attraction), [Lowden State Park](https://www.expedia.ca/Lowden-State-Park-Illinois.d553248621532658451.Vacation-Attraction) and [Conover Square Mall](https://www.expedia.ca/Conover-Square-Mall-Oregon.d626197998490935296.Vacation-Attraction) 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. ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/90cf0aed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel CA $829 per person May 25 - May 29 found 8 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (469 reviews) Room was amazing and beautiful and comfortable Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous Reviewed on Mar 1, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,207 per person May 18 - May 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago. Reviewed on Mar 14, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,051 per person May 18 - May 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Great stay! I will stay here again on my next trip back this summer! Reviewed on Mar 16, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $853 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Great stay! No complaints! Breakfast buffet was a great plus! Reviewed on Mar 15, 2026 ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/a75a4abb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $2,019 per person May 25 - May 29 found 8 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,006 reviews) Great location and property Reviewed on Mar 14, 2026 ## Ready to book your vacation to Oregon? Choose your dates ## Oregon Hotel Deals ![Paddle Wheel Inn](https://images.trvl-media.com/lodging/9000000/8960000/8958000/8957995/b6d97445_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Paddle Wheel Inn 1457 IL Rt 2 North Oregon IL Fully refundableReserve now, pay when you stay CA $115 CA $125 total Mar 22 - Mar 23 includes taxes & fees 8.8/10 Excellent! (697 reviews) a great last min accommodation. wonderful location, wonderful view. Reviewed on Mar 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=8957995&PinnedHotelID=8957995&HadPinnedHotel=true®ionId=55882) ![ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night](https://images.trvl-media.com/lodging/24000000/23530000/23526300/23526209/9acbfc95_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night Oregon IL 9.8/10 Exceptional! (146 reviews) The host was super accommodating and had great communication. The home had everything we needed and was warm and cozy. Reviewed on Dec 3, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=23526209&PinnedHotelID=23526209&HadPinnedHotel=true®ionId=55882) [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=23526209&PinnedHotelID=23526209&HadPinnedHotel=true®ionId=55882) ![Chateau Lodge](https://images.trvl-media.com/lodging/19000000/18750000/18742200/18742129/d3f1556a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chateau Lodge 1326 IL Route 2 N. Oregon IL Fully refundableReserve now, pay when you stay CA $88 CA $100 total Apr 8 - Apr 9 includes taxes & fees 8/10 Very Good! (132 reviews) Clean room Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=18742129&PinnedHotelID=18742129&HadPinnedHotel=true®ionId=55882) [See all 190 properties in Oregon](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F03%2F2026&endDate=18%2F03%2F2026®ionId=55882) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app