Oregon Vacation Packages
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Your Oregon Vacation
Uncover the very best of Oregon with a customized Oregon vacation package. From its lively atmosphere and progressive thinking to its spectacular views, you'll love getting to know this coastal city in your own way. Castle Rock State Park, Lowden State Park and Conover Square Mall are just a few of the many sights worth exploring during your trip to Oregon. No matter your travel plans or budget, organizing a tailored Oregon vacation is simple with Expedia.
Top Oregon Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,202, price is now CA $833 per person
CA $833
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that
Reviewed on Jun 12, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,919, price is now CA $1,261 per person
CA $1,261
per person
Sep 3 - Sep 7
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.
Reviewed on Jun 14, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,014, price is now CA $1,402 per person
CA $1,402
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (484 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,296, price is now CA $1,604 per person
CA $1,604
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
This is our second time staying at the sable and it was wonderful! The staff is amazing and friendly! The elevators were out and we got lost a couple times getting to our room, and every single staff member that we would run into each time was so helpful and kind in finding where we were supposed to go! One of the housekeepers even stopped what she was doing to walk us to our correct floor when she realized we were lost! She was so incredibly nice! The views are incredible, the location is incredible, and the staff is incredible! Will definitely be coming back on our next trip to Chicago/Navy Pier!
Reviewed on Jun 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $4,048, price is now CA $2,901 per person
CA $2,901
per person
Sep 1 - Sep 8
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
The fitness center & spa was top notch. The on site restaurant had amazing food and service.
Reviewed on Jun 12, 2026
Oregon Hotel Deals
Paddle Wheel Inn
1457 IL Rt 2 North Oregon IL
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Jun 16 to Jun 17
CA $117
CA $127 total
Jun 16 - Jun 17
includes taxes & fees
8.8/10 Excellent! (722 reviews)
"If you get a hot tub room, make sure you ask at the front desk for a shower mat. If you don’t and you try to take a shower without one, you will find yourself slipping all over the sloped hot tub floor. Not sure why this isn’t provided up front. Also, the room smelled a bit musty."
Reviewed on Jun 11, 2026
Chateau Lodge
1326 IL Route 2 N. Oregon IL
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Jun 17 to Jun 18
CA $90
CA $102 total
Jun 17 - Jun 18
includes taxes & fees
8/10 Very Good! (140 reviews)
"Very well kept and neat cool place"
Reviewed on Jun 1, 2026
ROCK RIVER HIDEAWAY
Oregon IL
9.8/10 Exceptional! (151 reviews)
"The property sits on the Rock River and you can watch the river flow from several locations inside and outside. Very calming and relaxing. Pet-friendly."
Reviewed on Jun 8, 2026
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.
Stay near popular Oregon attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
