Oregon Vacation Packages 2026 from $413

Oregon flight + hotel vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$413

per person

May 21 - May 24

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 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$608

per person

May 21 - May 24

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

$475

per person

Apr 30 - May 3

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.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$539

per person

May 21 - May 24

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. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$519

per person

May 21 - May 24

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 hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Top Oregon hotels deals

Paddle Wheel Inn

1457 IL Rt 2 North Oregon IL

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$96 total

Feb 28 - Mar 1

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 Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

Oregon IL

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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

Oregon IL

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This vacation home features barbecue grills.

Kitchen

Air conditioning

Unique Victorian Cottage Close to Town

Oregon IL

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

Kitchen

Washer

Holiday Inn Rockford by IHG

7550 E State Street Rockford IL

Free Cancellation

$107 nightly

$122 total

Mar 15 - Mar 16

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

Embassy Suites by Hilton Rockford Riverfront

416 S Main Street Rockford IL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$177 total

Mar 22 - Mar 23

Total with taxes and fees

This hotel features 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at one of the 2 bars/lounges and enjoy the free buffet breakfast each morning.

Pool

Breakfast included

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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.

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.

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 $413. 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.