Oregon Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.

Top Oregon Vacation Deals

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 7 - Jun. 10
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on Apr. 14, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 2 - Jun. 5
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 1 - Jul. 6
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on Apr. 15, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 2 - Jun. 5
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Every single person working at this facility was extremely polite and welcoming. I’ve stayed in so many hotels across the world and I have to say this was the best experience I’ve ever had staying at a hotel. Ordered food at 3am and it was fantastic. My cloths got folded in the short period of time my wife and I left the room and came back to a spotless room. Overall amazing experience. Will be staying here every time I come to Chicago.

Reviewed on Apr. 16, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 2 - Jun. 5
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar. 16, 2024

Prices and availability subject to change. Additional terms may apply.

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
The price is CA $94 per night from Apr. 29 to Apr. 30
CA $94
CA $102 total
includes taxes & fees
Apr 29 - Apr 30
8.6/10 Excellent! (553 reviews)
"Great location and very friendly staff. Wish they offered breakfast."

Reviewed on Mar. 26, 2024

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
The price is CA $98 per night from Apr. 21 to Apr. 22
CA $98
CA $107 total
includes taxes & fees
Apr 21 - Apr 22
8/10 Very Good! (87 reviews)
"Loved it"

Reviewed on Aug. 21, 2023

Chateau Lodge
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
Oregon
10/10 Exceptional! (23 reviews)
Perfect Cozy Cabin for Family Holiday Visit
"This is my second time staying at this Rock River cabin. Our first visit was this past summer, and of course it was great being outside and on the river. This visit was for a family Thanksgiving trip, and we took full advantage of the warm, cozy gas fireplace in the family room. It was fantastic! ..."

Reviewed on Nov. 28, 2023

Get rates
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
See all 156 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Oregon vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Oregon from just CA $708. And the more you bundle, the more cash you save. Your dream vacation has never been so affordable.
How do I get a cheap travel package to Oregon?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we’ve got it all. Pick and choose a combination that suits you and see your savings pile up. We know a package deal is never one-size-fits-all. That’s why Expedia offers over 550 airlines and 1,000,000 hotel options across the world, which lets you customize your Oregon adventure.
Where should I stay in Oregon?
Stay where the action is. Many people favor hotels within easy reach of popular attractions, like Castle Rock State Park, Lowden State Park and Conover Square Mall.
What are the top hotels in Oregon?
Secure a room at Rock River Hideaway Outdoor Activities. It’s one of this neighborhood’s most in-demand hotels. Another highly rated option in Oregon is Chateau Lodge.
How far in advance should I book my Oregon vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. A number of air carriers advertise tickets up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Oregon sometimes emerge just a few weeks before departure.
What does an Expedia Oregon travel package include?
Rental cars, flights and hotels, or any combination of them — the choice is yours. Whether you’re exploring Oregon with the kids or enjoying a solo break, there’s a package to suit every style and budget. Once you’ve made your booking, why not add on a couple of tours as well?
What should I know before booking an Oregon travel package?
Our prices are always low. However, you’ll enjoy even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you’ll get transparent pricing and tons of choice.
Can I choose my airline with an Oregon Expedia vacation package?
Yes, you’re in control. We have access to over 550 airlines globally, so you can customize your Oregon vacation according to your budget and style.
If I'm not able to travel, can I cancel my Oregon vacation package?
It’s good to know that you can cancel your Oregon booking if your plans have changed. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Oregon

Image for Castle Rock State Park

Castle Rock State Park

Explore the great outdoors at Castle Rock State Park, a lovely green space in Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.

Castle Rock State Park
Image for Lowden State Park

Lowden State Park

Explore the great outdoors at Lowden State Park, a lovely green space in Oregon. Stroll along the area's riverfront or simply enjoy its restaurants.

Lowden State Park
Image for Conover Square Mall

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

Other vacations you might like

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