Oregon Holidays from £1,267

Book a Hotel + Flight or Car together to unlock savings

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Your Oregon Holiday

Book a Oregon holiday package and get ready to experience the highlights of this city. Consider staying in the neighbourhood 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 holiday is a walk in the park with Expedia.

Top Oregon Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
Price was £1,907, price is now £1,267 per person
£1,267
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.4/10 Very Good! (1,011 reviews)
There was employee strike going on at the Hotel and lots of noise. Rooms are extremely small and not much choice for breakfast.

Reviewed on 26 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,303, price is now £1,465 per person
£1,465
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Perfect location! Friendly staff. Beautiful room overlooking skyline and water.

Reviewed on 26 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £2,172, price is now £1,399 per person
£1,399
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,020, price is now £1,307 per person
£1,307
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Great property. Clean and convenient. Only unsightly thing is that there was a dirty t shirt laying in the hallway that nobody seemed to pick up.

Reviewed on 26 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £3,518, price is now £2,330 per person
£2,330
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

Oregon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Population
10,000
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Henry Vilas Zoo, Overture Centre for the Arts and Orpheum Theatre

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 £68 per night from 15 Sept to 16 Sept
£68
15 Sept - 16 Sept
includes taxes & fees
9.2/10 Wonderful! (296 reviews)
"The front desk personelle was VERY attentive and helpful. Hot tub has option of indoor and outdoor. Nice dining options within walking distance. Nice shower. Comfortable beds. Overall a very nice hotel!"

Reviewed on 26 Aug 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
The price is £145 per night from 10 Sept to 11 Sept
£145
10 Sept - 11 Sept
includes taxes & fees
9.4/10 Exceptional! (3,006 reviews)
"Staff was so helpful and friendly. Everything was clean and looked great. Great location. Only place I stay when I come to Madison."

Reviewed on 23 Aug 2025

The Madison Concourse Hotel and Governor's Club
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is £69 per night from 7 Sept to 8 Sept
£69
7 Sept - 8 Sept
includes taxes & fees
AmericInn by Wyndham Madison West
See all 483 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oregon travel package cost?
Be ready to book, because a trip to Oregon starts from an enticing £1,267. When you combine your flights, hotels and more into a travel package, you'll score the lowest prices.
If I'm not able to travel, can I cancel my Oregon travel package?
Yes, you can. We understand that life happens, so we're here to help if you need to make changes to your Oregon travel package. It may be possible to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Oregon?
Book everything in the one place with our Oregon travel packages. You'll discover bargains on hotels, flights and more that'll keep your bank account happy and adventurous side satisfied. And, with more than 550 partner airlines and 1,000,000 properties worldwide to choose from, you'll have the flexibility to mix and match as you like.
Does Expedia offer Book Now, Pay Later Oregon holidays?
We do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in manageable instalments. Simply choose the payment plan that suits best during the checkout process and take the stress out of budgeting for your trip. Be sure to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your trip over multiple transactions.
  • Low deposit holidays: When you come across an awesome deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you secure your getaway.

Where should I stay in Oregon?
Oregon is home to several fascinating places to discover, such as Legend at Bergamont. Spend your nights in a hotel nearby and make sightseeing easier.
What are the top hotels in Oregon?
If this will be your first visit to Oregon, secure a room at Harbour Shores on Lake Geneva or Mt. Olympus Water & Theme Park Resort. Both offer friendly service and are popular options with many travellers.
How far in advance should I book my Oregon holiday?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers display prices up to 12 months prior to take off. Usually, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Oregon are still known to appear just a few weeks before departure.
What does an Expedia Oregon travel package include?
That depends on you. You can choose from a range of Oregon bundles, such as a hotel, rental car and flight. You can also book a hotel and a flight, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your dream Oregon escape looks like, you're sure to save!
What should I know before booking an Oregon travel package?
You'll land impressive savings when you bundle your flights, hotels and rental cars into a travel package. Not just that, booking everything in one place makes trip planning easier. So why waste your time or money? Whether you're putting together an upscale romantic escape or a low-cost family road trip, browse our travel packages today.
Can I choose my airline with an Oregon Expedia travel package?
Most definitely. Expedia has more than 550 airline partners to pick from worldwide. With so much choice, finding the right carrier to take you to Oregon will be a breeze.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.