Oregon Vacations from $176

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $341, price is now $176 per person
$176
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
I had the pleasure of staying with this hotel during a recent work trip. They were as lovely as can be, the hotel and room were very clean, and the included breakfast buffet exceeded all my expectations. The area had a lot to see and was easily walkable. Looking forward to my next Chicago trip so I can stay here again.

Reviewed on Oct 28, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $738, price is now $379 per person
$379
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
We loved the Pendry!

Reviewed on Oct 27, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $805, price is now $422 per person
$422
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Excellent stay. The hotel staff is very courteous and helpful, and the location is great!

Reviewed on Oct 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $828, price is now $454 per person
$454
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Easy check-in, friendly staff, beautiful building with nice amenities.

Reviewed on Oct 27, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $560, price is now $312 per person
$312
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 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 Nov 2 to Nov 3
$83 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (678 reviews)
👍

Reviewed on Oct 25, 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
$64 nightly
The price is $69 total per night from Nov 12 to Nov 13
$69 total
Nov 12 - Nov 13
Total with taxes and fees
7.8/10 Good! (125 reviews)
Quaint budget hotel
Everything worked as it should. Cute, golf themed room that was clean and comfortable. Good location and easy parking. Staff/owners were very friendly. Bathroom is a little dated, but very hot water with good pressure.

Reviewed on Oct 20, 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! (128 reviews)
Great location. Plenty of parking. Right on the Rock River. Very clean. Lots of outside seating on the decks. Lots of towels, though we couldn’t find them at first. They were in the dining room credenza. The house is pretty well stocked with supplies. The host is very friendly and responsive. Would ...

Reviewed on Sep 11, 2025

Get rates
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
See all 175 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.

Find the Best Oregon Vacation Packages

Oregon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
3,600
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Castle Rock State Park, White Pines Forest State Park and Lowden State Park

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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 $176 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.

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