Title: Oregon Vacation Packages & Trips 2026 from CA $1,057 | 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. ![Harbor Shores on Lake Geneva](https://images.trvl-media.com/lodging/1000000/10000/4700/4614/3a08fccc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Harbor Shores on Lake Geneva CA $1,057 per person Jun 3 - Jun 9 found 10 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,318 reviews) During off season not as many activities Reviewed on Mar 16, 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 $1,451 per person May 7 - May 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 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 $1,176 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Clean room. Very friendly staff Reviewed on Mar 25, 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 $1,325 per person Jun 5 - Jun 8 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Rooms are nice, great view, valet parking is great Reviewed on Mar 24, 2026 ![Lodge Geneva National](https://images.trvl-media.com/lodging/1000000/900000/893400/893361/c30b4670_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lodge Geneva National CA $1,404 per person Jun 3 - Jun 9 found 10 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,366 reviews) It was ok rooms were noisy can here everything in hall and in next room Reviewed on Mar 23, 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 Apr 2 - Apr 3 includes taxes & fees 8.8/10 Excellent! (700 reviews) Key card system is a complete mess after hours. Reviewed on Mar 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%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=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=23526209&PinnedHotelID=23526209&HadPinnedHotel=true®ionId=55882) [](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%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 184 properties in Oregon](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%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