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.
Baymont by Wyndham Glenview
Price was CA $768, price is now CA $557 per person
CA $557
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,004 reviews)
Breakfast was there but not a lot
Look at moving in individuals using it as a home
Good location though nice area around the place
Reviewed on May 9, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $2,632, price is now CA $1,645 per person
CA $1,645
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
The view is fantastic. You can see the Chicago river on one side, abd skyscraper on tge other side. The small items that the hotel provides, makes the stay, pleasant and homely.
Reviewed on May 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,355, price is now CA $1,579 per person
CA $1,579
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,700, price is now CA $1,206 per person
CA $1,206
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Oregon Hotel Deals
Paddle Wheel Inn
1457 IL Rt 2 North Oregon IL
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from May 14 to May 15
CA $108
CA $118 total
May 14 - May 15
includes taxes & fees
8.8/10 Excellent! (715 reviews)
Front desk was closed when we arrived. We called the phone # left on a sign for guest that were locked out of their room but no answer. I called the next day and the female that answered the phone was rude and extremely condescending.
Reviewed on May 9, 2026
Chateau Lodge
1326 IL Route 2 N. Oregon IL
Fully refundableReserve now, pay when you stay
The price is CA $86 per night from May 18 to May 19
CA $86
CA $102 total
May 18 - May 19
includes taxes & fees
8/10 Very Good! (137 reviews)
No breakfast, clean and great for the price.
Reviewed on May 10, 2026
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with a fee of 30.00 per night
Oregon IL
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
