Deals on vacations and trips to Oregon

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Oregon flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,332, price is now $826 per person
$826
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,649, price is now $1,167 per person
$1,167
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,452, price is now $1,046 per person
$1,046
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Downtown Chicago
Price was $1,274, price is now $927 per person
$927
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a terrace, and express check-out are also on offer.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,790, price is now $1,333 per person
$1,333
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and concierge services.

Top Oregon hotels deals

Paddle Wheel Inn

Paddle Wheel Inn

2 out of 5
1457 IL Rt 2 North Oregon IL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $83 total per night
$83 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a gym and a sauna. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.
Parking included
Free WiFi
ROCK RIVER HIDEAWAY

ROCK RIVER HIDEAWAY

Oregon IL
Get rates
This vacation home includes a garden and barbecue grills.
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N. Oregon IL
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $78 total per night
$78 total
Nov 1 - Nov 2
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and barbecue grills are also on offer.
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Oregon IL
Get rates
This vacation home features barbecue grills.
Kitchen
Air conditioning
Historic Cottage - Walk to Downtown & Trails

Historic Cottage - Walk to Downtown & Trails

Oregon IL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Riverview Inn & Suites, an Ascend Collection Hotel

Riverview Inn & Suites, an Ascend Collection Hotel

3 out of 5
700 W Riverside Blvd Rockford IL
Free Cancellation
$92 nightly
The price is $105 total per night
$105 total
Nov 1 - Nov 2
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Don't see what you're looking for?
See all available properties in Oregon
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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.

Stay near popular Oregon attractions

Castle Rock State Park

8.8/10 (55 reviews)
You can take time to visit Castle Rock State Park during your travels to Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.
See properties

Frequently asked questions

How much are vacation packages to Oregon?
Splash out on a fulfilling travel experience in Oregon with a vacation package starting at $826. Reserving hotels, flights and tours with Travelocity is simple. And even better, our vacation deals will leave you with more savings in your pocket for loads of fun activities.
How long should my Oregon vacation be?
If you're looking for some guidance, most travelers spend an average of 2 nights vacationing in Oregon. But to discover the true essence of this destination, stay a few extra nights. That way you can get to more attractions and really soak up the local culture.
Where can I get the best vacation package deals for Oregon?
Check out Travelocity. With access to 400 airlines and a massive 1,000,000 hotels around the world, creating the perfect Oregon package deal couldn't be simpler.
Why should I purchase my Oregon vacation package via Travelocity?
Because we believe in crafting unforgettable vacation experiences. From hotels and flights to car rentals and activities, our packages make it a breeze to save. Our customer care is available 24/7 to ensure you'll never roam alone. We also offer a Price Match Guarantee, so you can lock in your getaway knowing you've landed the best deal possible. Find a lower price and we'll match it!
Will I save money on my Oregon car rental if I bundle it with a hotel or flight?
Bundling your flight, hotel and car into an Oregon vacation package is the easiest way to score the best deal. Plus, having your own car rental gives you the freedom to find your way to all those big-name sights you can't wait to explore. Sitting 85 mi away from Oregon, Wrigley Field is one place that should have a place on your itinerary. Buckle up and make a day trip of it.
Which airport is best for Oregon?
Rockford, IL (RFD-Greater Rockford) is the best airport for those flying to Oregon. Once you touch down, you'll find yourself 18 mi northeast of downtown.
What is there to do in Oregon?
Oregon is teeming with places to discover, including Castle Rock State Park and Lowden State Park. These well-known attractions are at the top of most people's travel schedules.
Where should I stay when visiting Oregon?
The WHOLE ISLAND TO YOURSELF, boat included. Sleeps 10 people. is the first choice of many travelers. Book as soon as possible before it's too late.

Photos of local treasures

Browse Oregon vacation photos for more inspiration

A wooden bridge over a river surrounded by dense forest.
A large brick building with a prominent tower and arched windows.
A large stone statue of a woman standing in a park with a clear blue sky and lush green trees in the background.
A statue of a man holding a child in front of a building with a sign that reads "County."
A river with a rocky shore, surrounded by trees and mountains under a cloudy sky.

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