Book Exclusive Oregon Vacation Packages

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Oregon flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Morris

Super 8 by Wyndham Morris

2 out of 5
per person
Dec. 24 - Dec. 31
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly motel in Morris. Enjoy free breakfast, free WiFi, and free parking. Popular attractions AMC Classic Morris 10 and Echo Bowling Lanes are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Dec. 29 - Jan. 2
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Jan. 17 - Jan. 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Guesthouse Hotel

The Guesthouse Hotel

4 out of 5
Uptown
Save 100% on your flight
per person
Dec. 21 - Dec. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Dec. 23 - Dec. 25
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

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
The price is CA $101 per night
CA $101
CA $111 total
includes taxes & fees
18 Nov - 19 Nov
Book a stay at this business-friendly hotel in Oregon. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lowden State Park and Conover Square Mall are located nearby.
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
The price is CA $111 per night
CA $111
CA $121 total
includes taxes & fees
17 Nov - 18 Nov
Book a stay at this business-friendly motel in Oregon. Enjoy free WiFi, free parking, and room service. Popular attractions Lowden State Park and Conover Square Mall are located nearby.
Parking included
Free WiFi
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

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

Get rates
Stay at this vacation home in Oregon. Enjoy in-room jetted tubs, an in-room coffeemaker, and in-room fireplaces. Popular attractions Castle Rock State Park and Conover Square Mall are located nearby.
Kitchen
Air conditioning
Unique Victorian Cottage Close to Town

Unique Victorian Cottage Close to Town

Get rates
Stay at this cottage in Oregon. Enjoy free WiFi, a garden, and patios. Popular attractions Conover Square Mall and Lowden State Park are located nearby.
Kitchen
Washer
2 Bedroom Cul De Sac Cottage in Town

2 Bedroom Cul De Sac Cottage in Town

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Stay at this vacation home in Oregon. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Conover Square Mall and Lowden State Park are located nearby.
Kitchen
Washer
Holiday Inn Rockford, an IHG Hotel

Holiday Inn Rockford, an IHG Hotel

3 out of 5
7550 E State Street, Rockford, IL
Free cancellation
The price is CA $124 per night
CA $124
CA $141 total
includes taxes & fees
24 Nov - 25 Nov
Stay at this 3-star business-friendly hotel in Rockford. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rockford Casino and CoCo Key Water Resort are located nearby.
Pool
Free airport shuttle
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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

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

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

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

Oregon Vacations

It's always a good idea to know a bit about your destination before you hurry off on your vacation. Highlight Oregon on a map now and get set for a memorable adventure!

This town lies 13 miles (21 kilometers) northeast of Dixon. It's also 15 miles (24 kilometers) west of Rochelle.

Roughly 4,000 people live in this part of Illinois, so you'll have plenty of opportunities to make some new acquaintances.

Places to visit in Oregon

Hal Palmer Park is a green oasis amid the hustle and bustle of everyday life. Fling off your shoes and feel the cool grass below your feet or simply lie back and search for shapes in the clouds. Need more ideas? If you're bored of dining indoors, pick up some takeaway and enjoy a revitalizing lunch surrounded by the greenery of Dillehay Park. And that's not all. Are you looking to ease the stresses of urban life? Enjoy the fresh air as you take off on an adventure through Castle Rock State Park.

Where do you fly into for Oregon?

Coming in to land at Greater Rockford Airport (RFD)? Once you step off the aircraft, downtown Oregon is approximately 19 miles (31 kilometers) southwest away. Hail a cab and take a deep breath — your adventure has just begun!

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 CA $716. 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 137 kilometers 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 29 kilometers 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