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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,049, price is now CA $760 per person
CA $760
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
Very nice rooms. Smaller casino but nice. No late night food options.

Reviewed on Jul 9, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,834, price is now CA $1,264 per person
CA $1,264
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Room was clean and large, staff were helpful and polite. Would definitely stay again!

Reviewed on Jul 10, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.

Reviewed on Jul 9, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,287, price is now CA $1,612 per person
CA $1,612
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on Jul 8, 2026

Ready to book your vacation to Oregon?

 

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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 $105 per night from Aug 9 to Aug 10
CA $105
CA $119 total
Aug 9 - Aug 10
includes taxes & fees
9.4/10 Exceptional! (433 reviews)
"Mostly a good place except spotty wifi service"

Reviewed on Jul 7, 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 $210 per night from Aug 2 to Aug 3
CA $210
CA $242 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (3,978 reviews)
"We have stayed here twice in the last 6 months mainly because of the front desk staff and because it’s downtown. That being said we stayed 4 nights supposedly on the 3rd day housekeeping is suppose to clean our room but they did not arrive for that until after 5pm. We were at that time getting ready ..."

Reviewed on Jul 10, 2026

The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 12 to Jul 13
CA $184
CA $213 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Room was very small and there were scratch marks all over the walls"

Reviewed on Jul 10, 2026

Best Western Plus InnTowner Madison
See all 499 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.
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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 top-notch restaurants 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 $760 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.

Explore a world of travel with Expedia

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