Oregon Vacation Packages

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Flight and hotel packages to Oregon

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

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Self parking, limo/town car service, and express check-out are also offered.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This smoke-free hotel features 2 restaurants, 4 beach bars, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.

Top Oregon hotel 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 $76 per night
$76
per night
May 21 - May 22
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
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

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

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This vacation home features barbecue grills.
Fireplace
Kitchen
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 $76 per night
$76
per night
Jun 10 - Jun 11
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.
Charming Victorian cottage near the Rock River

Charming Victorian cottage near the Rock River

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This cottage features barbecue grills.
2 Bedroom Cul De Sac Cottage in Town

2 Bedroom Cul De Sac Cottage in Town

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This vacation home includes a garden and barbecue grills.
Pet friendly
Outdoor Space
Econo Lodge

Econo Lodge

2 out of 5
7712 Potawatomi Trail, Rockford, IL
Free Cancellation
Reserve now, pay when you stay
The price is $59 per night
$59
per night
May 26 - May 27
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A computer station is provided and the front desk is staffed around-the-clock.
Breakfast included
Pet friendly
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See all available properties in Oregon
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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 in Oregon

Image for Castle Rock State Park

Castle Rock State Park

4.5/5(23 reviews)

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

4/5(13 reviews)

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

Frequently asked questions

How much are vacation packages to Oregon?
Your vacation daydreams can all come true in Oregon for as little as $535. Our affordable package deals include flights and hotels, so booking your trip will be a cinch. The only thing you’ll have to worry about is having a good time.
How long should my Oregon vacation be?
Typically, visitors stay 2 nights in Oregon. Although, that might not be nearly long enough for you. If you’re eager to discover some of the area’s hidden gems, how about adding another few nights to your travel schedule?
Where can I get the best vacation package deals for Oregon?
Travelocity has countless ways to score a sensational Oregon package deal. Take your pick of 400 partner airlines and 1,000,000 properties around the world and create a vacation package that’s perfect for you. With so much choice, you have inspiration galore for your next big escape.
Why should I purchase my Oregon vacation package with Travelocity?
The three S’s — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to round-the-clock support. With the Travelocity Price Match Guarantee, you know you’re getting the best deal available.
Can I save money on my Oregon car rental if I book it with a hotel or flight?
Combining your hotel, car and flight into an Oregon vacation package is the easiest way to land the best prices. Plus, having your own set of wheels gives you absolute freedom to make your way to all those amazing sights you can’t wait to explore. Sitting 85 mi away from Oregon, Wrigley Field is one place that should be on your must-do list. Top up the tank and make a day trip of it.
What is the best time of year to go to Oregon?
If funds are a bit tight, is a fantastic month to explore Oregon, whereas is the dearest time of the year. April, June and September is generally regarded as high season. If you’d prefer to dodge the crowds, January, October and December tend to be quieter.
Which airport is best for Oregon?
Rockford, IL (RFD-Greater Rockford) is around 18 mi northeast of downtown Oregon.
What is there to do in Oregon?
Conover Square Mall should be on your travel itinerary. After you’ve crossed off this top attraction, simply roam through the streets of Oregon and find out what makes this cool place tick.
Where should I stay when visiting Oregon?
If you’re after somewhere to spend your nights, take a look at the Rock River Hideawayoutdoor Activitiesgrillfire Pitsatellite Tv Pet Friendly. It’s the top pick for many travelers.