Oregon Vacations from $233

Book a Hotel + Flight or Car together to unlock savings

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $435, price is now $233 per person
$233
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
Clean room, free wine bottle and water bottles were provided daily. Great location! Everything within 15-20 minute walk. Omar, the bartender was excellent and super friendly! Had great suggestions on where to go to eat and entertainment and made great drinks! I would stay there again and great price too!

Reviewed on Sep 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $897, price is now $506 per person
$506
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
The rooftop wss amazing and very friendly front desk. Even delivered birthday card and chocolates for the hubby.

Reviewed on Sep 28, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,006, price is now $570 per person
$570
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe

Reviewed on Sep 27, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,141, price is now $683 per person
$683
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September. Rooms were clean modern and had loads of desk space but no dressers or nightstands. Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily. We would stay there again.

Reviewed on Sep 26, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $413, price is now $249 per person
$249
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Always a pleasure to stay here!

Reviewed on Sep 27, 2025

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Discover the most popular places to visit in Oregon

Legend at Bergamont

Enjoy a round of golf in Oregon at Legend at Bergamont. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Legend at Bergamont

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
$85 nightly
The price is $97 total per night from Oct 14 to Oct 15
$97 total
Oct 14 - Oct 15
Total with taxes and fees
9.2/10 Wonderful! (311 reviews)
Great staff!!
"It was a great stay and the staff was incredible as she went and retrieved then held an item I left behind."

Reviewed on Sep 24, 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
$139 nightly
The price is $161 total per night from Oct 5 to Oct 6
$161 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (3,129 reviews)
"Every time we come to Madison we stay at this hotel. Perfect location and excellent service. My only complaint this time is that we requested service for the room on Sunday, left at noon, returned at around 8pm and room was not cleaned. This is the first time that had ever happened so I assume there ..."

Reviewed on Sep 24, 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
$71 nightly
The price is $82 total per night from Oct 6 to Oct 7
$82 total
Oct 6 - Oct 7
Total with taxes and fees
8/10 Very Good! (1,027 reviews)
"Nice place, would stay again."

Reviewed on Sep 24, 2025

Baymont by Wyndham Madison West/Middleton WI West
See all 480 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 an Oregon vacation package cost?
You'll find cheap prices from $233 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.