Oregon Vacation Packages
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Your Oregon Vacation
Book a Oregon vacation package and get ready to experience the highlights of this city. Consider staying in the neighborhood of Marquette, which is good for cycling, culture and fishing. Legend at Bergamont is among the big-ticket attractions to check off your itinerary during a trip to Oregon. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Oregon vacation is a walk in the park with Expedia.
Top Oregon Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
Price was CA $909, price is now CA $625 per person
CA $625
per person
Mar 28 - Apr 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
8/10 Very Good! (478 reviews)
Was an wonderful experience. The staff was very kind and helpful. The view was amazing. Highly recommend any time of the year!
Reviewed on Jan 12, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,332, price is now CA $857 per person
CA $857
per person
Apr 30 - May 3
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,120, price is now CA $795 per person
CA $795
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10
Reviewed on Feb 9, 2026
DoubleTree by Hilton Chicago - Alsip
Price was CA $998, price is now CA $732 per person
CA $732
per person
Mar 28 - Apr 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
Everything was perfect and the front desk was so nice
Reviewed on Feb 10, 2026
Aloft Chicago Downtown River North
Downtown Chicago
Price was CA $1,042, price is now CA $764 per person
CA $764
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Staff was great but next to fire station. Beware very noisy if staying city view
Reviewed on Feb 8, 2026
Oregon Hotel Deals
Sleep Inn & Suites Oregon - Madison
1120 Park Street Oregon WI
Fully refundable
The price is CA $99 per night from Mar 2 to Mar 3
CA $99
CA $112 total
Mar 2 - Mar 3
includes taxes & fees
9.2/10 Wonderful! (373 reviews)
Hotel was clean and very nice.
Reviewed on Jan 27, 2026
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Mar 13 to Mar 14
CA $233
CA $269 total
Mar 13 - Mar 14
includes taxes & fees
9.4/10 Exceptional! (3,477 reviews)
Great as always
Reviewed on Feb 3, 2026
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $77 per night from Mar 8 to Mar 9
CA $77
CA $89 total
Mar 8 - Mar 9
includes taxes & fees
8/10 Very Good! (1,159 reviews)
Great breakfast and all day coffee
Reviewed on Feb 3, 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.
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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.
