
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.

Level Chicago - River North
Downtown Chicago
per person
Oct 6 - Oct 10
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on Jul. 27, 2025

The Peninsula Chicago
Downtown Chicago
per person
Sep 25 - Sep 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!
Reviewed on Jul. 26, 2025


Hotel Riu Plaza Chicago
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
The location of the hotel right off Michigan Avenue was perfect. Public parking right across the street. The hotel is fresh and new. Many staff available to assist. Do not skip the complimentary breakfast! I would easy pay $20 for that breakfast as it had everything from fresh fruit, real eggs, pastries, even a coffee cream warmer/frother machine for the great coffee!
Reviewed on Aug. 6, 2025

Eurostars Magnificent Mile
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (3,055 reviews)
Had a lovely stay during the weekend and would likely stay here again in the near future. Staff always greeted me when leaving or entering the building every day and wished me well.
Reviewed on Aug. 4, 2025
Oregon Hotel Deals

Sleep Inn & Suites Oregon - Madison
1120 Park Street, Oregon, WI
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Aug 24 to Aug 25
CA $110
CA $125 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (282 reviews)
"It was very close to our event with family."
Reviewed on Aug. 2, 2025

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 $172 per night from Aug 10 to Aug 11
CA $172
CA $199 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (2,933 reviews)
"Great hotel and location!"
Reviewed on Aug. 3, 2025

Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Sep 2 to Sep 3
CA $92
CA $107 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,015 reviews)
"I can’t say enough great things about my stay at the Baymont Hotel West in Madison! From the moment I arrived, every staff member I encountered went above and beyond to make me feel welcome and taken care of. Their customer service is truly top-notch, friendly, professional, and always eager to help ..."
Reviewed on Aug. 4, 2025
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.