Oregon Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Oregon Flight & Hotel Packages

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

Hilton Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Beautiful hotel, quiet clean spacious rooms! Breakfast buffett to die for. Close to museums and Metro.

Reviewed on 24 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We had multiple issues with the locks on our door.

Reviewed on 24 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.

Reviewed on 20 Nov,2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Amazing boutique hotel located in downtown Chicago. The front desk staff were so helpful and considerate, as well as the restaurant on property offered multiple options for breakfast lunch dinner and cocktails!

Reviewed on 24 Nov,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Oregon

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 S$108 per night from 10 Dec to 11 Dec
S$108
includes taxes & fees
10 Dec - 11 Dec
9.2/10 Wonderful! (204 reviews)
Clean & Comfortable Hotel
"We were in town with our kids to visit friends and family for the weekend. The hotel was clean, beds were comfortable and the kids enjoyed the pool area. The front desk staff were pleasant and helpful. The kids and my husband said the free breakfast was good. Overall we enjoyed our stay and would ..."

Reviewed on 11 Nov,2024

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 S$173 per night from 1 Dec to 2 Dec
S$173
includes taxes & fees
1 Dec - 2 Dec
9.4/10 Exceptional! (2,104 reviews)
"Great customer service, clean, safe location."

Reviewed on 24 Nov,2024

The Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East
DoubleTree by Hilton Madison East
4 out of 5
4402 E Washington Ave, Madison, WI
Fully refundableReserve now, pay when you stay
The price is S$161 per night from 26 Nov to 27 Nov
S$161
includes taxes & fees
26 Nov - 27 Nov
9.2/10 Wonderful! (802 reviews)
"I arrived after dark so have rated the outsider grounds neutrally. The security provisions requiring cards for the elevator makes me feel more secure. Very clean and comfortable room!"

Reviewed on 21 Nov,2024

DoubleTree by Hilton Madison East
See all 486 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.

Frequently asked questions

How much does an Oregon holiday package cost?
Starting from only S$757, a package is your ticket to low-cost travel. Put together your Oregon getaway by choosing from our huge range of hotels, flights and rental cars.
How do I get a cheap travel package to Oregon?
Bundling your hotel and flight with Expedia won’t just save precious time — it’ll save you a nice amount too. An Oregon holiday package makes it easy to arrange your perfect trip. With more than 550 airlines throughout the world to pick from, finding convenient flights that suit your schedule won’t be hard. In addition to that, we have over 1,000,000 properties globally to take your pick of. Now that’s choice! No matter who you are, Expedia will help show you the world.
Where should I stay in Oregon?
Oregon is home to several terrific places to see, like Legend at Bergamont. Spend your evenings in a hotel near this attraction and make sightseeing easier.
What are the top hotels in Oregon?
When it comes to comfy and convenient places to stay in Oregon, you can’t beat Sleep Inn & Suites Oregon - Madison. Check out its deals and pick up a great price.
How far in advance should I book my Oregon holiday?
Reserving your flights early with Expedia means one less thing to worry about. Many air carriers advertise tickets up to 12 months in advance. Generally, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Oregon sometimes occur just a few weeks before departure.
What does an Expedia Oregon travel package include?
That mostly depends on you. You can pick from a range of Oregon bundles, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a rental car with a flight. Once you’ve made your booking, you can add the fun stuff like activities and experiences. Whatever your perfect Oregon holiday looks like, you’re sure to save!
What should I know before booking an Oregon travel package?
Our prices are always low. However, you’ll grab even more bargains when you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and lots of choice.
Can I choose my airline with an Oregon Expedia holiday package?
With a holiday package, you’re in control. Whether you’d prefer to fly to Oregon in economy or first class, simply select from the available airline options. Expedia has access to more than 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Oregon holiday package?
Whether it’s your hotel or flight, you can cancel or change it. Booked your Oregon holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings older than that, you may incur a fee from your hotel, airline or car rental company. For more information, look up our Customer Service Portal. We’ll help you each step of the way.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.