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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.
Grand Royal Hotel O'Hare - Chicago
Pendry Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Hotel Riu Plaza Chicago
Hilton Chicago O'Hare Airport
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Discover the most popular places to visit in Oregon

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
$88 nightly
The price is $96 total per night from Jan 15 to Jan 16
$96 total
Jan 15 - Jan 16
Total with taxes and fees
8.6/10 Excellent! (688 reviews)
Awesome views, clean rooms, quiet area walking distance to two nice restaurants. Overall great experience will be back for future stays!

Reviewed on Jan 10, 2026

Paddle Wheel Inn
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N. Oregon IL
8/10 Very Good! (132 reviews)
Clean room

Reviewed on Dec 13, 2025

Chateau Lodge
WHOLE ISLAND TO YOURSELF, boat included. Sleeps 8 people.

WHOLE ISLAND TO YOURSELF, boat included. Sleeps 8 people.

2 out of 5
Oregon IL
WHOLE ISLAND TO YOURSELF, boat included. Sleeps 8 people.
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

Things to do in and around Oregon

Oregon, Illinois is perfect for outdoor and adventure lovers, boasting a variety of recreational areas and campgrounds. Enjoy outdoor fun with scenic spots ideal for sightseeing. Whether you're hiking, fishing, or just soaking in the beautiful landscapes, there’s something for everyone. Don’t forget to explore local shopping options to complete your visit, making it a well-rounded destination for an unforgettable vacation.

Shopping

In Oregon, visit Conover Square Mall for a mix of shopping and entertainment. If you're up for a drive, check out CherryVale Mall, offering a larger selection of stores and family-friendly vibes, located 24 miles away, or Pepper Creek Gift & Flower Shop, also 24 miles from Oregon.

Recreation

At White Pines Forest State Park, immerse yourself in nature with serene hiking trails and calming scenery, perfect for relaxation. Levings Park offers tranquil spaces for yoga and mindfulness, enhancing your wellness journey. Meanwhile, the Historic Dixon Theatre provides a cultural escape with entertaining performances for a vibrant evening.

Adventure

Experience the thrill of freefall at Chicagoland Skydiving Center, located 16 miles from Oregon, where adventure meets adrenaline. For a fun-filled day, visit Hurricane Harbor Rockford, 25 miles away, offering exhilarating water rides. Don't miss The Cherry Bowl, an arcade Adventure Zone 24 miles from Oregon, perfect for family fun.

Nightlife

Oregon's nightlife features cozy bars and friendly local pubs. Visit the White Pines Restaurant for a casual dinner and drinks, then head to the Oregon VFW for live music and dancing. Enjoy a laid-back atmosphere that showcases the charm of small-town nightlife.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Oregon

Oregon, Illinois, offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal vacation spot. Visitors can explore local attractions like the national state park, a railway museum, and urban parks. For those seeking cultural and family experiences, highlights include the Oregon Zoo, the Oregon Coast, and the Wonders of Oregon. These points of interest ensure a memorable trip filled with exploration and enjoyment.

  • Dillehay Park: A delightful urban park located 5 miles from Oregon, Dillehay Park offers a family-friendly atmosphere with plenty of outdoor activities. Enjoy picnicking, walking trails, and playgrounds surrounded by lush greenery, making it a perfect spot for relaxation and recreation.
  • Stillman's Defeat Memorial Site: Situated 10 miles from Oregon, this memorial site commemorates a significant historical event. It provides a cultural experience, allowing visitors to reflect on local history and the stories of those who fought in the conflict, making it a meaningful stop for history enthusiasts.
  • Rochelle Railroad Park: Located 15 miles away, this unique railway museum immerses visitors in the rich history of railroads. Explore exhibits showcasing vintage trains and learn about the impact of railroads on American culture, making it an engaging destination for families and history buffs alike.

Best time to go to Oregon

The best time to visit Oregon is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.2°F (-6.0°C)Light RainMostly CloudyModerately LowSlightly Low
February23.9°F (-4.5°C)Light RainMostly CloudyAverageSlightly Low
March37.6°F (3.1°C)Light RainMostly CloudyAverageAverage
April48.0°F (8.9°C)Light RainMostly CloudyAverageAverage
May60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
June69.4°F (20.8°C)Light RainMostly SunnyModerately HighSlightly High
July72.5°F (22.5°C)Light RainMostly SunnyModerately HighSlightly High
August71.1°F (21.7°C)Light RainMostly SunnyAverageSlightly High
September64.8°F (18.2°C)Light RainMostly SunnyModerately HighAverage
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November39.2°F (4.0°C)Light RainMostly SunnyModerately LowAverage
December29.3°F (-1.5°C)Light RainMostly CloudyModerately LowSlightly Low

Tips to save on your trip to Oregon

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Oregon during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $334 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.