Oregon Vacations from $329
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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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $634, price is now $329 per person
$329
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,161, price is now $1,148 per person
$1,148
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Room exceptional well kept, staff extremely nice Ms Diana in the front desk and Luis in the concierge were superb
Reviewed on Nov 10, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $854, price is now $474 per person
$474
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special
Reviewed on Nov 11, 2025
Park Hyatt Chicago
Downtown Chicago
Price was $1,079, price is now $605 per person
$605
per person
Jan 22 - Jan 26
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
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 lively breweries while you're in the area.
Oregon Hotel Deals
Sleep Inn & Suites Oregon - Madison
1120 Park Street, Oregon, WI
Fully refundable
$82 nightly
The price is $93 total per night from Dec 9 to Dec 10
$93 total
Dec 9 - Dec 10
Total with taxes and fees
9.2/10 Wonderful! (326 reviews)
Quiet, clean and comfortable bed. Friendly Staff
Reviewed on Oct 28, 2025
The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
$139 nightly
The price is $161 total per night from Nov 16 to Nov 17
$161 total
Nov 16 - Nov 17
Total with taxes and fees
9.4/10 Exceptional! (3,280 reviews)
Dee and Zachary continue to provide excellent service! Rooms are clean and location can’t be beat
Reviewed on Nov 7, 2025
Best Western Plus InnTowner Madison
2424 University Avenue, Madison, WI
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $135 total per night from Nov 17 to Nov 18
$135 total
Nov 17 - Nov 18
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
The staff are very nice and helpful.
Reviewed on Nov 11, 2025
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
