Oregon Vacation Packages 2026 from $495

Oregon flight + hotel vacation packages

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

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$495

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$667

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$628

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Holiday Inn Express & Suites Prospect Heights by IHG

Save 100% on your flight

$510

per person

Jul 13 - Jul 20

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$1,060

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

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 29 - Apr 30

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

$74 nightly

$81 total

Apr 29 - Apr 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

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

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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

Reserve now, pay when you stay

$96 nightly

$110 total

May 10 - May 11

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.

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

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 $495. 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.