Oregon Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,293, price is now CA $987 per person
CA $987
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Staff was great and the room was clean!

Reviewed on Oct 29, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,870, price is now CA $1,374 per person
CA $1,374
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $3,076, price is now CA $2,269 per person
CA $2,269
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
My only suggestions. The batteries in the rechargeable TV remotes die too quickly and the room service ordering software on the tablet was lacking pictures. Options for an omelet were red and unavailable to select. So unless they were out of eggs, that was an issue. And the bedside tablet nightlight is nice, but too bright. These were a struggle to come up with because the service was impeccable.

Reviewed on Oct 30, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,417, price is now CA $1,050 per person
CA $1,050
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,619, price is now CA $1,219 per person
CA $1,219
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Ready to book your vacation to Oregon?

 

Choose your dates

Oregon Hotel Deals

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

2.5 out of 5
1120 Park Street Oregon WI
Fully refundable
The price is CA $100 per night from Nov 22 to Nov 23
CA $100
CA $113 total
Nov 22 - Nov 23
includes taxes & fees
9.4/10 Exceptional! (475 reviews)
"Excellent"

Reviewed on Oct 27, 2026

Sleep Inn & Suites Oregon - Madison
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Nov 8 to Nov 9
CA $165
CA $191 total
Nov 8 - Nov 9
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Fully refundable
The price is CA $62 per night from Nov 10 to Nov 11
CA $62
CA $71 total
Nov 10 - Nov 11
includes taxes & fees
6.2/10 (1,059 reviews)
"They sold my room after I had booked it with Expedia and had my confirmation number. And when I called the staff was very rude and disrespectful"

Reviewed on Oct 28, 2026

Motel 6 Madison, WI - East
See all 531 properties in Oregon
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Stay near popular Oregon attractions

Legend at Bergamont

Enjoy a round of golf in Oregon at Legend at Bergamont. Attend a sporting event or simply enjoy the lively breweries while you're in the area.
See properties

Frequently asked questions

How much does a Oregon vacation package cost?
Offering great value package deals from CA $987 on Expedia, you'll be pleasantly surprised at how much a vacation to Oregon costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Oregon?
January, July and November are great times to search for cheap Oregon vacation packages. Travelling in less busy periods means you can usually find lower prices on accommodations and flights.
How many days is enough for Oregon?
Typically, a handful of days is enough to go to the major sights during your Oregon vacation. However, if you prefer to have time to kick back or go on day trips, think about extending your itinerary.
How to find the best Oregon package deals?
Begin your search for a Oregon package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Oregon package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oregon adventure underway.
Is it cheaper to book a Oregon vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights individually. Better still, you can customize your Oregon escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oregon?
If you're planning an impromptu Oregon vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Oregon?

  1. Pick your dates: The things you want to do in Oregon and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in expenses like flights, food and transportation when working out how much to set aside for your trip to Oregon. Then, select a property that fits your budget, whether that's an economical option or a lavish getaway.
  3. Decide your trip length: Think about how long you want to spend discovering Oregon. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Oregon vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.