Oregon Vacations from $863
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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.
The Latest Oregon vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,198
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go.
There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable.
We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles.
Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult.
The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.
Reviewed on Sep 28, 2026
Level Chicago Fulton Market
Downtown Chicago
$976
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.
Reviewed on Sep 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$870
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
This property was clean and comfy. We really enjoyed the sauna and steam room. The staff at the spa were super sweat and friendly.
Reviewed on Sep 28, 2026
Stay near popular Oregon attractions
Legend at Bergamont
Designed by two-time U.S. Open Champion Andy North, this championship course earned Golf Digest's "Top 10 New Courses" honor. Visitors enjoy resort amenities including pool, tennis, and panoramic clubhouse views.
Oregon Hotel Deals
Sleep Inn & Suites Oregon - Madison
1120 Park Street Oregon WI
Fully refundable
$77 nightly
$88 total
Oct 26 - Oct 27
Total with taxes and fees
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$150 nightly
$173 total
Oct 25 - Oct 26
Total with taxes and fees
9.4/10 Exceptional! (4,210 reviews)
"Great"
Reviewed on Sep 28, 2026
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
$139 nightly
$161 total
Oct 4 - Oct 5
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
"Very clean and friendly staff. Our room had a musty smell though and I was not a fan of the sliding bathroom door. Overall very happy with our stay. A great breakfast."
Reviewed on Sep 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.
Find the Best Oregon Vacation Packages
Oregon Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Dane County Regional Airport (MSN) |
Population | 10,000 |
Top Sights | Henry Vilas Zoo, Overture Center for the Arts and Orpheum Theater |
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Frequently asked questions
How much does an Oregon vacation package cost?
You'll find cheap prices from $863 on Expedia for your Oregon break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oregon costs.
What are the cheapest months to go to Oregon?
November, December and January are great times to look for cheap Oregon vacation packages. Traveling in quieter months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Oregon?
The ideal duration for your Oregon vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to tick off all the top attractions and discover some hidden treasures along the way.
How to find the best Oregon package deals?
Bagging a cheap Oregon package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oregon package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Oregon vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Oregon vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Oregon?
If you're considering an impromptu Oregon vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Oregon vacation packages?
Set off on your dream getaway to Oregon with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
