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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $784, price is now $422 per person
$422
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,322, price is now $641 per person
$641
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $976, price is now $486 per person
$486
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Price was $2,047, price is now $1,078 per person
$1,078
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $841, price is now $458 per person
$458
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A terrace, a snack bar/deli, and a lobby fireplace are also on offer.

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
Aug 27 - Aug 28
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
$83 nightly
The price is $90 total per night
$90 total
Sep 21 - Sep 22
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.
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

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Pet friendly
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

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

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This vacation home features barbecue grills.
WHOLE ISLAND TO YOURSELF, boat included. Sleeps 8 people.

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

2 out of 5
Get rates
This cabin features a garden, laundry facilities, and barbecue grills.
2 Bedroom Cul De Sac Cottage in Town

2 Bedroom Cul De Sac Cottage in Town

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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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.

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 $422. 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