Oregon Vacation Packages 2026 from $274

Oregon flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Illinois Beach Hotel

Save 100% on your flight

$274

per person

May 19 - May 23

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

$385

per person

May 17 - May 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$651

per person

May 29 - May 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$810

per person

Jul 4 - Jul 9

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

$511

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Top Oregon hotels deals

Paddle Wheel Inn

1457 IL Rt 2 North Oregon IL

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$89 total

Apr 17 - Apr 18

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

1326 IL Route 2 N. Oregon IL

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$69 total

Apr 19 - Apr 20

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

ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with a fee of 30.00 per night

Oregon IL

Get rates

This vacation home includes a garden and barbecue grills.

Kitchen

Pet friendly

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

Oregon IL

Get rates

This vacation home features barbecue grills.

Kitchen

Air conditioning

Cozy Cottage Near Town & Nature — Great for Long Stays

Oregon IL

Get rates

This cottage features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Riverview Inn & Suites, an Ascend Collection Hotel

700 W Riverside Blvd Rockford IL

Free Cancellation

$95 nightly

$109 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. 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

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

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.

Lowden State Park

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.

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.

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 $274. 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.