Oregon Vacations from $580

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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.

The Latest Oregon vacation packages

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

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $859, price is now $580 per person
$580
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Best location on Michigan Avenue

Reviewed on Jun 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,358, price is now $849 per person
$849
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Resort living in the city!

Reviewed on Jun 28, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,166, price is now $753 per person
$753
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!

Reviewed on Jun 25, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,067, price is now $713 per person
$713
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,134 reviews)
Hotel is phenomenal and location is beyond.

Reviewed on Jun 26, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,023, price is now $701 per person
$701
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.

Reviewed on Jun 28, 2026

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Stay near popular Oregon attractions

Legend at Bergamont

Designed by two-time U.S. Open Champion Andy North, this championship course earned Golf Digest's "Top 10 New Courses" honor. Visitors enjoy resort amenities including pool, tennis, and panoramic clubhouse views.
See properties

Oregon Hotel Deals

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

2.5 out of 5
1120 Park Street Oregon WI
Fully refundable
$75 nightly
The price is $86 total per night from Jul 26 to Jul 27
$86 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (425 reviews)
"Air conditioning broke in room. Would not give me a receipt on check out."

Reviewed on Jun 28, 2026

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
$139 nightly
The price is $161 total per night from Jul 5 to Jul 6
$161 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (3,905 reviews)
"nice hotel for a show at the orpheum"

Reviewed on Jun 28, 2026

The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $120 total per night from Jun 30 to Jul 1
$120 total
Jun 30 - Jul 1
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"Very pleasant staff"

Reviewed on Jun 27, 2026

Best Western Plus InnTowner Madison
See all 497 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.

Find the Best Oregon Vacation Packages

Oregon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Population
10,000
Top Sights
Henry Vilas Zoo, Overture Center for the Arts and Orpheum Theater

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Frequently asked questions

How much does an Oregon vacation package cost?
You'll find cheap prices from $580 on Expedia for your Oregon break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oregon costs.
What are the cheapest months to go to Oregon?
November, December and January are great times to look for cheap Oregon vacation packages. Traveling in quieter months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Oregon?
The ideal duration for your Oregon vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to tick off all the top attractions and discover some hidden treasures along the way.
How to find the best Oregon package deals?
Bagging a cheap Oregon package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oregon package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Oregon vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Oregon vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Oregon?
If you're considering an impromptu Oregon vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Oregon vacation packages?
Set off on your dream getaway to Oregon with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.