Oregon Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,637, price is now CA $2,438 per person
CA $2,438
per person
Sep 12 - Sep 18
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,387, price is now CA $975 per person
CA $975
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,771, price is now CA $1,956 per person
CA $1,956
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Oregon Hotel Deals
Sleep Inn & Suites Oregon - Madison
1120 Park Street Oregon WI
Fully refundable
The price is CA $110 per night from Jul 12 to Jul 13
CA $110
CA $124 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (425 reviews)
"Air conditioning broke in room. Would not give me a receipt on check out."
Reviewed on Jun 28, 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 $168 per night from Jul 5 to Jul 6
CA $168
CA $194 total
Jul 5 - Jul 6
includes taxes & fees
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Jul 4 to Jul 5
CA $148
CA $170 total
Jul 4 - Jul 5
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Very pleasant staff"
Reviewed on Jun 27, 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.
Stay near popular Oregon attractions
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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.
