Oregon Vacation Packages

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Your Oregon Vacation

Book a Oregon vacation package and get ready to experience the highlights of this city. Consider staying in the neighborhood of Marquette, which is good for cycling, culture and fishing. Legend at Bergamont is among the big-ticket attractions to check off your itinerary during a trip to Oregon. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Oregon vacation is a walk in the park with Expedia.

Top Oregon Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Oct 6 - Oct 10
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul. 27, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 25 - Sep 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
The location of the hotel right off Michigan Avenue was perfect. Public parking right across the street. The hotel is fresh and new. Many staff available to assist. Do not skip the complimentary breakfast! I would easy pay $20 for that breakfast as it had everything from fresh fruit, real eggs, pastries, even a coffee cream warmer/frother machine for the great coffee!

Reviewed on Aug. 6, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (3,055 reviews)
Had a lovely stay during the weekend and would likely stay here again in the near future. Staff always greeted me when leaving or entering the building every day and wished me well.

Reviewed on Aug. 4, 2025

Ready to book your vacation to Oregon?

 

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Oregon Hotel Deals

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

2.5 out of 5
1120 Park Street, Oregon, WI
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Aug 24 to Aug 25
CA $110
CA $125 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (282 reviews)
"It was very close to our event with family."

Reviewed on Aug. 2, 2025

Sleep Inn & Suites Oregon - Madison
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Aug 10 to Aug 11
CA $172
CA $199 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (2,933 reviews)
"Great hotel and location!"

Reviewed on Aug. 3, 2025

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Sep 2 to Sep 3
CA $92
CA $107 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,015 reviews)
"I can’t say enough great things about my stay at the Baymont Hotel West in Madison! From the moment I arrived, every staff member I encountered went above and beyond to make me feel welcome and taken care of. Their customer service is truly top-notch, friendly, professional, and always eager to help ..."

Reviewed on Aug. 4, 2025

Baymont by Wyndham Madison West/Middleton WI West
See all 481 properties in Oregon
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.
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Frequently asked questions

How much does a Oregon vacation package cost?
Offering great value package deals from CA $1,051 on Expedia, you'll be pleasantly surprised at how much a vacation to Oregon costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Oregon?
January, July and November are great times to search for cheap Oregon vacation packages. Travelling in less busy periods means you can usually find lower prices on accommodations and flights.
How many days is enough for Oregon?
Typically, a handful of days is enough to go to the major sights during your Oregon vacation. However, if you prefer to have time to kick back or go on day trips, think about extending your itinerary.
How to find the best Oregon package deals?
Begin your search for a Oregon package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Oregon package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oregon adventure underway.
Is it cheaper to book a Oregon vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights individually. Better still, you can customize your Oregon escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oregon?
If you're planning an impromptu Oregon vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Oregon?

  1. Pick your dates: The things you want to do in Oregon and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in expenses like flights, food and transportation when working out how much to set aside for your trip to Oregon. Then, select a property that fits your budget, whether that's an economical option or a lavish getaway.
  3. Decide your trip length: Think about how long you want to spend discovering Oregon. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Oregon vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.