$282 Cheap flights to Oregon County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap flights to Oregon County from $282 One Way, $559 Round Trip

$559 return flights and $282 one-way flights to Oregon County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Nov 15 - Wed, Nov 18
ORD
Chicago
TBN
Fort Leonard Wood
$559 Roundtrip, found 14 hours ago
$559
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sun, Nov 15 from Chicago to Fort Leonard Wood, returning Wed, Nov 18, priced at $559 found 14 hours ago
Sun, Nov 15 - Wed, Nov 18
ORD
Chicago
TBN
Fort Leonard Wood
$565 Roundtrip, found 14 hours ago
$565
Roundtrip
found 14 hours ago
Select Delta flight, departing Sun, Nov 15 from Chicago to Fort Leonard Wood, returning Wed, Nov 18, priced at $565 found 14 hours ago
Sun, Nov 15 - Wed, Nov 18
ORD
Chicago
TBN
Fort Leonard Wood
$569 Roundtrip, found 14 hours ago
$569
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sun, Nov 15 from Chicago to Fort Leonard Wood, returning Wed, Nov 18, priced at $569 found 14 hours ago
Sun, Nov 15 - Wed, Nov 18
ORD
Chicago
TBN
Fort Leonard Wood
$570 Roundtrip, found 14 hours ago
$570
Roundtrip
found 14 hours ago
Select Delta flight, departing Sun, Nov 15 from Chicago to Fort Leonard Wood, returning Wed, Nov 18, priced at $570 found 14 hours ago
Sun, Nov 15 - Wed, Nov 18
ORD
Chicago
TBN
Fort Leonard Wood
$595 Roundtrip, found 14 hours ago
$595
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sun, Nov 15 from Chicago to Fort Leonard Wood, returning Wed, Nov 18, priced at $595 found 14 hours ago
Sun, Nov 15 - Wed, Nov 18
ORD
Chicago
TBN
Fort Leonard Wood
$646 Roundtrip, found 14 hours ago
$646
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sun, Nov 15 from Chicago to Fort Leonard Wood, returning Wed, Nov 18, priced at $646 found 14 hours ago
Loading

Deals For This Weekend's Flights

Find The Perfect Hotel For After Your Flight

Score Epic Oregon County Accommodation Deals

Holiday Inn Express & Suites West Plains Southwest by IHG

Holiday Inn Express & Suites West Plains Southwest by IHG

2.5 out of 5
1301 Preacher Roe Blvd West Plains MO
Fully refundable
$130 nightly
The price is $149 total per night from Oct 22 to Oct 23
$149 total
Oct 22 - Oct 23
Total with taxes and fees
Book a stay at this business-friendly hotel in West Plains. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (410 reviews)
"Everything was perfect!!! Thank you so much!!"

Reviewed on Oct 7, 2026

Opens in a new windowHoliday Inn Express & Suites West Plains Southwest by IHG
Cottonwood Inn

Cottonwood Inn

2.5 out of 5
360 Highway 62 East Salem AR
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $61 total per night from Nov 11 to Nov 12
$61 total
Nov 11 - Nov 12
Total with taxes and fees
Stay at this motel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews.
8/10 Very Good! (416 reviews)
"They need something indicating where their driveway is. They could fix damaged doors , main and bathroom. The air conditioner, heater had warped grating that I was afraid to use it."

Reviewed on Oct 12, 2026

Opens in a new windowCottonwood Inn
Baymont by Wyndham West Plains

Baymont by Wyndham West Plains

2.5 out of 5
1605 Imperial Drive West Plains MO
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $107 total per night from Oct 14 to Oct 15
$107 total
Oct 14 - Oct 15
Total with taxes and fees
Book a stay at this business-friendly hotel in West Plains. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowBaymont by Wyndham West Plains
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Quality Inn West Plains

Quality Inn West Plains

2.5 out of 5
220 Jan Howard Expy West Plains MO
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $118 total per night from Oct 15 to Oct 16
$118 total
Oct 15 - Oct 16
Total with taxes and fees
Book a stay at this business-friendly hotel in West Plains. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
8.6/10 Excellent! (770 reviews)
"Y"

Reviewed on Oct 12, 2026

Opens in a new windowQuality Inn West Plains
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Oregon County

Reach your destination without breaking your budget by booking your flights to Oregon County using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Oregon County Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Oregon County flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Oregon County. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Oregon County, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Oregon County flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

.

Frequently asked questions

Which airlines fly to Oregon County?
With 12 airlines waiting to help you get away to Oregon County, finding the perfect flight will be easy. Lock in your airfare with one of these top carriers with services to Lambert-St. Louis Intl. Airport (STL):

  • Air Canada - 35 flights to Oregon County per month
  • Frontier Airlines - 17 flights to Oregon County per month
  • Lufthansa - 3 flights to Oregon County per month

How much is a flight to Oregon County?
Return flight prices dropped as low as $559 this past week to Oregon County, and peaked at $646. Several lucky passengers departing Chicago (ORD) managed to snare one-way tickets from just $282.
How to book the cheapest flight to Oregon County?
Scoring cheap flights to Oregon County is as simple as booking your ticket with Orbitz. But if you'd like to make sure you're grabbing the best flight deals around, here are some suggestions to keep your wallet happy:

  • Consider departing from or arriving at nearby airports to save on your flight. Enter your preferred departure and arrival points in the form fields, then choose the 'Nearby airports' function below. It will list your options, if any.
  • If you're flexible with when you take off, click on the 'Show flexible dates' option. It'll show the flight deals for the days either side of your chosen departure. Ticket prices often vary depending on the day of the week.
  • Hit 'Show options' to narrow down your search results. You can choose your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • The early bird catches the biggest savings, so book as soon as you know your travel dates. The most affordable fares sell like hotcakes and prices generally increase as the departure date nears.
  • Make greater savings on your vacation by bundling your hotel, flights and car rental into an Orbitz package. Your budget will thank you for it.
  • Flying during busier seasons often means costly airfares. Try to vacation outside of popular dates, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Oregon County?
Generally speaking, January is the best month to book your plane ticket. This is followed by February and August. Keep this in mind while you look for a cheap flight to Oregon County.
What day of the week is the cheapest to book a flight to Oregon County?
Land a fantastic flight deal by booking on a Tuesday, Wednesday or Saturday. These are typically the best days of the week to score cheap airfares to Oregon County.
What is the cheapest day of the week to fly to Oregon County?
If you're on the hunt for cheap flights to Oregon County, depart at the start of the week. Orbitz data from 2020 shows Monday is the most affordable day to set off, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your wallet a favor.
What is the cheapest month to fly to Oregon County?
Get set to jet for less in August. This is generally the best month to take off if you're after cheap flights to Oregon County, based on Orbitz data. The least affordable time to fly is June, so try to avoid this month if you're on a budget.
Which airlines allow free cancellation?
When you search for flights on Orbitz, select "Filter by flexible change policies." This filter will quickly find all the airlines offering free cancellation within 24 hours of booking and no change fees. Relax knowing that if your travel dates change, your ticket can too.
What do I need for the flight to Oregon County?
Flying doesn't have to be a drag. In fact it can be a joy if you're well prepared! Make your trip a relaxing one with the following handy hints:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any issues during check-in, make sure that the name on your ticket is the same as on your government-issued photo ID.
  • To keep you busy on the short trip to Oregon County, download some new tunes or restock the audiobook library on your phone. Food can also be a nice distraction while in the air, so take a snack.
  • Whatever the temperature is doing outside, plane cabins can get a bit chilly. Take a light jacket on board to keep yourself cozy.

How do I get cheap first-class/business deals to Oregon County?
There are ways of booking first or business-class airfares to Oregon County that won't burn a hole through your budget. Grab a seat at the front of the plane for less with these handy tips:

  • Flexibility is important. By being open to other travel dates, you'll have better odds of picking up a great deal on your airfares.
  • Search for a low-cost airline that offers business-class seats. They usually come with more legroom and a glass of Champagne — but without the high price.
  • Take advantage of your airline's frequent flyer program and upgrade your seat. You can also bid for an upgrade in an online auction.

What is the best time to go to Oregon County?
Oregon County is an exciting getaway destination year-round, but the most popular months are March, May and June. If you love warmer weather, visit in summertime. Like most places in the Northern Hemisphere, the summer season kicks off June 20. Temperatures normally hover between 65 ºF and 90 ºF during the daytime.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.