Oregon Holidays from £1,014

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Your Oregon Holiday

Uncover the very best of Oregon with a customised Oregon holiday 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, organising a tailored Oregon holiday is simple with Expedia.

Top Oregon Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) 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

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 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Loved the view from the room of Lake Michigan.

Reviewed on 25 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 21 hours 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 21 hours 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

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 21 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.4/10 Very Good! (1,011 reviews)
Bed was comfortable, breakfast good, room VERY small

Reviewed on 24 Aug 2025

Oregon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
3,600
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Castle Rock State Park, White Pines Forest State Park and Lowden State Park

Top hotels in Oregon

Paddle Wheel Inn

Paddle Wheel Inn

2 out of 5
1457 IL Rt 2 North, Oregon, IL
Fully refundableReserve now, pay when you stay
The price is £58 per night from 27 Aug to 28 Aug
£58
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (663 reviews)
"Beautiful view of the river."

Reviewed on 22 Aug 2025

Paddle Wheel Inn
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N., Oregon, IL
Fully refundableReserve now, pay when you stay
The price is £71 per night from 27 Aug to 28 Aug
£71
27 Aug - 28 Aug
includes taxes & fees
7.8/10 Good! (115 reviews)
"This was very good and clean."

Reviewed on 3 Jul 2025

Chateau Lodge
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

Oregon, IL
9.6/10 Exceptional! (124 reviews)
Family Getaway
"Plenty of room for family of 5. We enjoyed the outdoor deck space and fire pit."

Reviewed on 3 Aug 2025

Get rates
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
See all 176 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.
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Frequently asked questions

How much does an Oregon travel package cost?
Starting from an incredible £1,014, you can tailor your Oregon package the way you want. Simply combine flights, hotels and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Oregon travel package?
Plans can change unexpectedly, so yes. You may be able to cancel or amend your Oregon travel package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make the necessary changes, but your hotel, car rental company or airline may charge a fee. Looking for more information? Visit our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Oregon?
Bundle your bookings with Expedia to save on your next big adventure. With over 550 air carriers and 1,000,000 hotels globally, your Oregon travel package can be tailored exactly to suit your budget. With all that extra money, why not add one or two interesting tours and experiences? It's an easy way to unlock even more savings. Your dream holiday in Oregon is closer than you thought!
Does Expedia offer Book Now, Pay Later Oregon holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book an incredible getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying a little each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your trip across multiple transactions.
  • Low deposit holidays: When you want to grab an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Oregon?
With fascinating attractions like Castle Rock State Park and Lowden State Park in this area, look for a hotel positioned near either one. Conover Square Mall is another Oregon hot spot that visitors flock to.
What are the top hotels in Oregon?
Get your holiday off to a flying start by staying at Hyatt Regency Chicago. It's one of most popular hotels in Oregon. Another comfortable option is The Godfrey Hotel Chicago.
How far in advance should I book my Oregon holiday?
It can be tricky to know when is the perfect time to book your Oregon trip. But typically the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels nearly a year before your departure date. If you're thinking of a last-minute getaway, no need to fret! There are great bargains advertised on Expedia all the time.
What does an Expedia Oregon travel package include?
With Expedia, you can choose any combination of hotels, flights and car rentals to create your ideal Oregon travel package. Once you've made your booking, you can add on all the fun stuff like tours and experiences. Remember — the more you bundle, the more discounts you'll get!
What should I know before booking an Oregon travel package?
We already have low prices. However, you'll score even more savings if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a huge range of choice.
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 many choices, finding the perfect carrier to get 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.