Oregon Holidays from £1,042

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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.
Chicago Marriott Southwest at Burr Ridge

Chicago Marriott Southwest at Burr Ridge

4 out of 5
Price was £1,296, price is now £1,042 per person
£1,042
per person
11 Sept - 17 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Close to a shopping and restaurant area , loved it .

Reviewed on 28 Jun 2026

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was £1,766, price is now £1,328 per person
£1,328
per person
11 Sept - 17 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (1,041 reviews)
Great hotel. Checked in and staff were friendly. The star of this hotel are the manager Maya!!! She was amazing to speak to and had a warm presence. There was a breakfast attendant we had on our second day that was also very nice but I cant remember her name. Will definitely stay here again as the hotel is very secure and clean.

Reviewed on 25 Jun 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
Price was £1,974, price is now £1,536 per person
£1,536
per person
31 Jul - 4 Aug
found 1 hour ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.

Reviewed on 28 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,822, price is now £1,437 per person
£1,437
per person
31 Jul - 4 Aug
found 1 hour ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
Very nice hotel in a central and safe location

Reviewed on 27 Jun 2026

Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Price was £1,944, price is now £1,556 per person
£1,556
per person
31 Jul - 5 Aug
found 4 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
No reviews

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 £69 per night from 5 Jul to 6 Jul
£69
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (727 reviews)
"Very nice place for a good price."

Reviewed on 22 Jun 2026

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 £55 per night from 2 Jul to 3 Jul
£55
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very good! (143 reviews)
"Nice, comfortable, clean place near town and places to spend a night or 2 chillaxing."

Reviewed on 28 Jun 2026

Chateau Lodge
ROCK RIVER HIDEAWAY

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 8 Jun 2026

Get rates
ROCK RIVER HIDEAWAY
See all 191 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

Castle Rock State Park

8.8/5 (55 reviews)
Perched atop a sandstone bluff, Castle Rock State Park offers panoramic views of the Rock River and rolling hills. Hike the scenic trails in autumn to witness a breathtaking display of vibrant foliage.
See properties

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.