Oregon Holidays from £1,308

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,959, price is now £1,308 per person
£1,308
per person
4 Sept - 11 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,703, price is now £1,644 per person
£1,644
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!

Reviewed on 13 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,642, price is now £1,672 per person
£1,672
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Clean rooms, nice pool, location great

Reviewed on 12 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was £2,363, price is now £1,503 per person
£1,503
per person
13 Sept - 20 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Great location and amazing AC in the room

Reviewed on 12 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,733, price is now £1,806 per person
£1,806
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Booked this stay for my husband Birthday. Wanted to make sure he enjoyed himself as well as me. I spent over $800 for the corner room, check in is at 4pm and we arrived about 430ish. Got to the room and the Amenities I purchased wasn’t there which was $100(they stated it would be at 4pm) which is why I want to arrive later. I noticed that the bed sheets were ripped, small stains on the couch in front of bed and the seat in the corner by the window that creeped me out. So we left and via Hilton app I contacted the Hotel to find out why my paid Amenities wasn’t there and they sat them in there while we were gone to dinner. We got back and the chocolate covered strawberries were melted. The best part about the stay was the firework show. My husband and I enjoyed ourselves as best we could after noticing these issues it was disgusting seeing the stains and the ripped sheets especially paying what was over $1000 for one night

Reviewed on 13 Jul 2026

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 refundable
The price is £67 per night from 12 Aug to 13 Aug
£67
12 Aug - 13 Aug
includes taxes & fees
9.4/10 Exceptional! (437 reviews)
"The hot tub is amazing"

Reviewed on 12 Jul 2026

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 £125 per night from 2 Aug to 3 Aug
£125
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (3,999 reviews)
"Great stay! The room was clean, comfortable, and quiet. The hotel was in a fantastic location, making it easy to walk to restaurants and explore downtown Madison. The staff was friendly and helpful, and everything was well maintained. We’d definitely stay here again!"

Reviewed on 12 Jul 2026

The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is £117 per night from 31 Jul to 1 Aug
£117
31 Jul - 1 Aug
includes taxes & fees
9.2/10 Wonderful! (1,020 reviews)
"Very nice and clean"

Reviewed on 11 Jul 2026

Best Western Plus InnTowner Madison
See all 499 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

Stay near popular Oregon attractions

Legend at Bergamont

Designed by two-time US Open Champion Andy North, this championship course earned Golf Digest's "Top 10 New Courses" honour. Visitors enjoy resort amenities including pool, tennis, and panoramic clubhouse views.
See properties

Frequently asked questions

How much does an Oregon travel package cost?
Be ready to book, because a trip to Oregon starts from an enticing £1,308. 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.

Explore a world of travel with Expedia

* 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.