Oregon Vacations from $284

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Your Oregon Vacation

Uncover the very best of Oregon with a customized Oregon vacation package. From its lively atmosphere and progressive thinking to its spectacular views, you'll love getting to know this coastal city in your own way. Castle Rock State Park, Lowden State Park and Conover Square Mall are just a few of the many sights worth exploring during your trip to Oregon. No matter your travel plans or budget, organizing a tailored Oregon vacation is simple with Expedia.

The Latest Oregon vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
Price was $508, price is now $284 per person
$284
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,007 reviews)
It was a very nice place. I don’t agree with the parking fees and then the added on three dollar Eco fee when nursing to be parking right beside it that was the cities and didn’t seem like very of secure parking. It wasn’t fenced in or anything just I don’t understand the fee for the parking Other night. It was a stay

Reviewed on Aug 24, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $2,412, price is now $1,327 per person
$1,327
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug 10, 2025

Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $723, price is now $420 per person
$420
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,019 reviews)
Nice staff! Clean and cozy room.

Reviewed on Aug 28, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
Price was $655, price is now $381 per person
$381
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,306 reviews)
Clean safe quiet excellent shuttle service

Reviewed on Aug 29, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,055, price is now $617 per person
$617
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug 21, 2025

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Discover the most popular places to visit in Oregon

Conover Square Mall

You can do some window-shopping at Conover Square Mall during your trip to Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.

Conover Square Mall

Oregon Hotel Deals

Paddle Wheel Inn

Paddle Wheel Inn

2 out of 5
1457 IL Rt 2 North, Oregon, IL
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $83 total per night from Sep 1 to Sep 2
$83 total
Sep 1 - Sep 2
Total with taxes and fees
Paddle Wheel Inn
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N., Oregon, IL
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Sep 8 to Sep 9
$86 total
Sep 8 - Sep 9
Total with taxes and fees
Chateau Lodge
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

Oregon
Get rates
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
See all 176 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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Frequently asked questions

How much does an Oregon vacation package cost?
You can snap up a vacation package to this destination from $284 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?
If you're hoping to score a cheap Oregon vacation package, consider traveling in January, October and December. You'll usually find lower rates on flights and accommodations during these months — ideal for a budget-friendly break.
How many days is enough for Oregon?
Usually, a handful of days is enough to tick off the main attractions during your Oregon vacation. However, if you want to have more time to kick back or go on day tours, think about extending your itinerary.
Is it worth booking a vacation package to Oregon?
Whether you're planning to discover attractions such as Castle Rock State Park and Lowden State Park, or eager to experience its terrific culture and nature, an Oregon vacation is sure to exceed your expectations. Book your trip with Expedia and discover why Oregon is such a good vacation destination.
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.
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. No need to scrimp and save or wait until the next payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snap up bargains before they disappear.

Explore a world of travel with Expedia

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.