Oregon Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Timothy Kilkenny
- 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
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.
Arlo Chicago
Downtown Chicago
Price was CA $1,302, price is now CA $820 per person
CA $820
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
Very clean and the staff were extremely professional and punctual!
Reviewed on Sep. 8, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,903, price is now CA $1,148 per person
CA $1,148
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Location, cleanliness, and friendly staff
Reviewed on Sep. 7, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,352, price is now CA $827 per person
CA $827
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
The staff were very friendly and helpful, and the location in the city is excellent. My only complaint is that the walls are quite thin, so you can easily hear noise from the surrounding rooms.
Reviewed on Sep. 8, 2025
Level Chicago - River North
Downtown Chicago
Price was CA $1,759, price is now CA $1,142 per person
CA $1,142
per person
Oct 24 - Oct 29
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (679 reviews)
Rooms could be updated. Staff was under trained. Amenities very nice, used family room daily with our toddler. Pool deck very modern and new
Reviewed on Sep. 8, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,051, price is now CA $1,357 per person
CA $1,357
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Oregon Hotel Deals
Sleep Inn & Suites Oregon - Madison
1120 Park Street, Oregon, WI
The price is CA $112 per night from Sep 15 to Sep 16
CA $112
CA $127 total
Sep 15 - Sep 16
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
The price is CA $173 per night from Sep 14 to Sep 15
CA $173
CA $200 total
Sep 14 - Sep 15
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from Sep 22 to Sep 23
CA $89
CA $103 total
Sep 22 - Sep 23
includes taxes & fees
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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
