Oregon Vacations from ￥58,476
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The Latest Oregon Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
￥58,476
per person
Nov 24 - Nov 27
found 21 hours ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
The staff was extremely accommodating, it was marathon week so I understand things can be tough, my issues were with the room as a whole. The shower would leak into the bathroom and completely cover the floor and when I informed staff I was having flooding problems they said oh it’s the shower curtain as if it’s a common issue. The wall paper in the bathroom was peeling off the wall. Tv guide didn’t work so you get to play channel roulette. On the plus side staff was great and they provided cold drinks in the morning, ac works really well
Reviewed on Oct 14, 2026
Swissotel - Chicago
Downtown Chicago
￥66,276
per person
Nov 24 - Nov 27
found 22 hours ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Beautiful location by Chicago river. We used parking with spot hero app and valet was very helpful,in showing us how to get to our parking location. Room was spacious and clean. Beds were comfortable. Staff was helpful
Reviewed on Oct 14, 2026
Find the Best Oregon Vacation Packages
Oregon Hotel Deals
Paddle Wheel Inn
1457 IL Rt 2 North Oregon IL
Fully refundableReserve now, pay when you stay
￥11,405
￥12,428 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (759 reviews)
"Spacious clean room, loved the sliding glass door out to our own patio, beautiful view of the river and Chief Blackhawk statue. The only thing needed is a non slip bath mat the bottom of the tub is very slippery. The staff were friendly and helpful. Would definitely come stay again."
Reviewed on Oct 14, 2026
Chateau Lodge
1326 IL Route 2 N. Oregon IL
Fully refundableReserve now, pay when you stay
￥10,879
￥12,330 total
Nov 2 - Nov 3
includes taxes & fees
8.2/10 Very Good! (160 reviews)
"Room was clean and well maintained. Just a little dated but overall very nice."
Reviewed on Sep 20, 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.
Stay near popular Oregon attractions
Castle Rock State Park
8.8/10 (55 reviews)
Perched atop a sandstone bluff, Castle Rock State Park offers panoramic views of the Rock River and rolling hills. Hike the scenic trails in autumn to witness a breathtaking display of vibrant foliage.
Lowden State Park
8.8/10 (31 reviews)
Gaze up at the towering 48-foot Eternal Indian statue overlooking Rock River's scenic bluffs. Hike through hardwood forests or reserve a campsite to fully experience this tranquil Illinois retreat.
Conover Square Mall
8.6/10 (16 reviews)
Once a piano factory, this historic mall houses specialty shops, antiques, and a model railroad exhibit. Wander through its charming maze of hallways to discover handcrafted treasures and nostalgic architectural details.
Frequently asked questions
How much does an Oregon vacation package cost?
You can snap up a vacation package to this destination from ￥58,476 on Expedia. However, how much your vacation to Oregon costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Oregon?
December, January and February are great times to search for cheap Oregon vacation packages. Choosing to travel in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Oregon?
The ideal length of your Oregon vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you time to check out all the main sights and explore some hidden spots along the way.
Is it worth booking a vacation package to Oregon?
During your Oregon vacation, you can count on experiencing some excellent nature and culture. Leave enough time in your itinerary to discover major sights like Castle Rock State Park and Lowden State Park.
How to find the best Oregon package deals?
Use Expedia's filters to find some tempting Oregon package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Oregon package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Oregon vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Oregon vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Oregon?
If you're considering a spontaneous Oregon trip, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Oregon?
- Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Oregon.
- Set a budget: Factor in costs like transportation, flights and meals when working out how much to put aside for your trip to Oregon. Then, choose a hotel that matches your budget, whether that's an affordable stay or a more luxurious retreat.
- Decide how long to go away for: Now that you're up to speed on Oregon, you can work out the ideal length of your vacation. Create a rough plan and allocate enough time to cover everything you want to do.
- Combine your airfare and accommodations: Once you've settled on your travel dates and duration, book the perfect Oregon vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
