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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $323, price is now $207 per person
$207
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,234, price is now $685 per person
$685
per person
Mar 2 - Mar 6
found 22 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $512, price is now $301 per person
$301
per person
Feb 14 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $446, price is now $287 per person
$287
per person
Mar 2 - Mar 6
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

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
$88 nightly
The price is $96 total per night
$96 total
Dec 14 - Dec 15
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
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N. Oregon IL
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $86 total per night
$86 total
Dec 29 - Dec 30
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. A garden, a picnic area, and barbecue grills are also on offer.
Parking included
Free WiFi
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
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 IL
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Pet friendly
WHOLE ISLAND TO YOURSELF, boat included. Sleeps 8 people.

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

2 out of 5
Oregon IL
Get rates
This cabin features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Holiday Inn Rockford by IHG

Holiday Inn Rockford by IHG

3 out of 5
7550 E State Street Rockford IL
Free Cancellation
$82 nightly
The price is $93 total per night
$93 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like a free area shuttle.
Pool
Free airport shuttle
Don't see what you're looking for?
See all available properties in Oregon
View all properties
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.

Popular places to visit

Castle Rock State Park

4.5/5(23 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.

Castle Rock State Park

Lowden State Park

4/5(13 reviews)

You can take time to visit Lowden State Park during your travels to Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.

Lowden State Park

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

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 $207. 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

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