Oregon Holidays

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    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Oregon

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Doorman was delightful! King room was spacious. Toilet flush was problematic. The pool was not open despite the advertisement on the Expedia websit. Lots of additional, non-negotiable charges once you get there.

Reviewed on 11 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
18 Sept - 22 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on 11 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
18 Sept - 22 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on 11 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
18 Sept - 22 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Beautiful hotel in great location. The food option at hotel are great with good food. It is walkable to surrounding attractions.

Reviewed on 10 Aug 2025

Top hotels in Oregon

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 €68 per night from 20 Aug to 21 Aug
€68
20 Aug - 21 Aug
includes taxes & fees
8.6/10 Excellent! (659 reviews)
"I loved our room with a balcony overlooking the river. Would like to come back to check out restaurants next to the motel."

Reviewed on 10 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 €82 per night from 21 Aug to 22 Aug
€82
21 Aug - 22 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.

Frequently asked questions

How much does an Oregon holiday package cost?
You can snap up a holiday package to this destination from €727 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.