Oregon Holidays from AU$2,911

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Your Oregon Holiday

Uncover the best parts of Oregon with a customised Oregon holiday package. From its lively atmosphere and progressive thinking to its spectacular views, you'll love discovering this coastal city on your own terms. Castle Rock State Park, Lowden State Park and Conover Square Mall are just some of the sights you'll want to check out during your trip to Oregon. Your ultimate Oregon holiday is only clicks away. Browse hotels, flights and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Oregon Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,586 reviews)
We had corner king room and it was very nice! We saw the city and the pool. The only thing I didn’t like was no complimentary water and cookies like most hotels. Sometimes the water be on point after walking and traveling. It’s thoughtful.

Reviewed on 12 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on 11 Aug. 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Location can’t be beat. Hotel is excellent!

Reviewed on 12 Aug. 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Everything was beautiful close to dining and shopping the beds were comfortable it was so relaxing looking out the window unto the ocean. Don’t hesitate book now

Reviewed on 11 Aug. 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
17 Oct - 24 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
It was exceptional all the way around

Reviewed on 10 Aug. 2025

Oregon Holiday

Oregon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
3,600
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Castle Rock State Park, White Pines Forest State Park and Lowden State Park

Our pick of the best 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
The price is AU$121 per night from 20 Aug to 21 Aug
AU$121
20 Aug - 21 Aug
includes taxes & fees
8.6/10 Excellent! (658 reviews)
"Beautiful area, clean place"

Reviewed on 8 Aug. 2025

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
The price is AU$146 per night from 13 Aug to 14 Aug
AU$146
13 Aug - 14 Aug
includes taxes & fees
7.8/10 Good! (115 reviews)
"This was very good and clean."

Reviewed on 3 Jul. 2025

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
9.6/10 Exceptional! (124 reviews)
Wonderful Stay
"we had such a peaceful weekend getaway here! the river views were absolutely stunning — seriously one of the best parts of the stay. the house itself was clean, cozy, and well-stocked, with everything we needed to relax. communication with the owner was super fast and smooth, which made the whole ..."

Reviewed on 14 Jul. 2025

Get rates
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
See all 177 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 holiday package cost?
You can snap up a holiday package to this destination from AU$2,911 on Expedia. However, how much your holiday 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 holiday packages. Choosing to travel in quieter months means you can generally find lower prices on accommodation and flights.
How many days is enough for Oregon?
The ideal length of your Oregon holiday 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 holiday package to Oregon?
During your Oregon holiday, 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 holiday package as soon as possible.
Is it cheaper to book an Oregon holiday as a package?
Expedia holiday 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 holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Oregon.
  2. 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.
  3. 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 holiday. Create a rough plan and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodation: Once you've settled on your travel dates and duration, book the perfect Oregon holiday package for you.

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