$69 Cheap Flights from Chicago (ORD) to Fort Leonard Wood (TBN)

View $69 flight on Sun, Jul 20, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Fort Leonard Wood (ORD-TBN)

Prices were available within the past 7 days and start at $69 for one-way flights and $139 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Wed, Jul 16 - Fri, Aug 1
ORD
Chicago
TBN
Fort Leonard Wood
$139 Roundtrip, found 9 hours ago
$139
Roundtrip
found 9 hours ago
Select Contour Airlines flight, departing Wed, Jul 16 from Chicago to Fort Leonard Wood, returning Fri, Aug 1, priced at $139 found 9 hours ago
Contour Airlines
Wed, Jul 16 - Wed, Aug 6
ORD
Chicago
TBN
Fort Leonard Wood
$148 Roundtrip, found 9 hours ago
$148
Roundtrip
found 9 hours ago
Select Contour Airlines flight, departing Wed, Jul 16 from Chicago to Fort Leonard Wood, returning Wed, Aug 6, priced at $148 found 9 hours ago
Contour Airlines
Thu, Jul 24 - Fri, Aug 8
ORD
Chicago
TBN
Fort Leonard Wood
$158 Roundtrip, found 9 hours ago
$158
Roundtrip
found 9 hours ago
Select Contour Airlines flight, departing Thu, Jul 24 from Chicago to Fort Leonard Wood, returning Fri, Aug 8, priced at $158 found 9 hours ago
Contour Airlines
Wed, May 7 - Wed, May 14
ORD
Chicago
TBN
Fort Leonard Wood
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Wed, May 7 from Chicago to Fort Leonard Wood, returning Wed, May 14, priced at $168 found 2 days ago
Contour Airlines
Wed, May 7 - Sun, May 11
ORD
Chicago
TBN
Fort Leonard Wood
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Wed, May 7 from Chicago to Fort Leonard Wood, returning Sun, May 11, priced at $178 found 1 day ago
Contour Airlines
Thu, Jul 17 - Wed, Aug 6
ORD
Chicago
TBN
Fort Leonard Wood
$189 Roundtrip, found 9 hours ago
$189
Roundtrip
found 9 hours ago
Select Contour Airlines flight, departing Thu, Jul 17 from Chicago to Fort Leonard Wood, returning Wed, Aug 6, priced at $189 found 9 hours ago
Contour Airlines
Thu, Jul 10 - Sun, Jul 27
ORD
Chicago
TBN
Fort Leonard Wood
$198 Roundtrip, found 9 hours ago
$198
Roundtrip
found 9 hours ago
Select Contour Airlines flight, departing Thu, Jul 10 from Chicago to Fort Leonard Wood, returning Sun, Jul 27, priced at $198 found 9 hours ago
Contour Airlines
Wed, May 7 - Tue, May 13
ORD
Chicago
TBN
Fort Leonard Wood
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Wed, May 7 from Chicago to Fort Leonard Wood, returning Tue, May 13, priced at $203 found 2 days ago
Contour Airlines
Wed, May 7 - Sun, May 11
ORD
Chicago
TBN
Fort Leonard Wood
$208 Roundtrip, found 10 hours ago
$208
Roundtrip
found 10 hours ago
Select Contour Airlines flight, departing Wed, May 7 from Chicago to Fort Leonard Wood, returning Sun, May 11, priced at $208 found 10 hours ago
American Airlines
Tue, May 20 - Thu, Jun 5
ORD
Chicago
TBN
Fort Leonard Wood
$218 Roundtrip, found 6 days ago
$218
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, May 20 from Chicago to Fort Leonard Wood, returning Thu, Jun 5, priced at $218 found 6 days ago
Flights from Chicago (ORD) to Fort Leonard Wood (TBN)
Origin airport
O'Hare Intl.
Destination airport
St. Robert Regional
Airlines serving
Contour Airlines
Roundtrip price
$138
Distance
369 mi

Chicago to Fort Leonard Wood Flights

The cheapest times to fly from Chicago to Fort Leonard Wood

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Fort Leonard Wood are during the month of July. You can find some of the cheapest flights from Chicago to Fort Leonard Wood with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Fort Leonard Wood

Sunday is one of the best days to book for cheap flights from Chicago to Fort Leonard Wood: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Fort Leonard Wood

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Fort Leonard Wood in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Fort Leonard Wood flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Fort Leonard Wood airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN) cost?
Cheap return fares from O’Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN) start from $139. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Contour Airlines flight leaving ORD on May 16 2025 and touching down at TBN. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from ORD to TBN?
The cheapest flights from ORD to TBN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN)?
Board a direct flight with Contour Aviation and fly straight from O’Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN).
What is the cheapest airline that flies from ORD to TBN?
At the moment, the cheapest airline offering one-way flights from ORD to TBN is Contour Airlines. You can take off on this route from $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on June 12 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN)?
On average, you can take your pick of 5 direct flights flying from O’Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN) each week. If you can’t see one that fits your travel plans, think about taking a flight with a layover. Customize your search results on Expedia to include one stop or more and select the next best alternative.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN)?
Flights between ORD and TBN are their busiest at 11 AM. If you’d like a quieter trip and possibly cheaper fares, look for a time when demand is lower.
What day of the week has the most flights from ORD to TBN?
Sunday offers the most flights from O’Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN). Consider taking off on this day and you’ll have the best chance of finding a departure that fits your plans.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN)?
The earliest flight departing from O’Hare Intl. Airport (ORD) is at around 11:45AM UTC-6. Board this plane and you’ll arrive at Waynesville Regional Airport (TBN) at approximately 1:25PM UTC-6. The total travel time is 1h 40m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN)?
The average flight time from ORD to TBN is 1 hour and 40 minutes, covering a total distance of 370 mi.
What airline has the least delays from ORD to TBN?
United Airlines has the best performance for on-time direct flights from O’Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN), with an on-time score of 83%. Use the Expedia App to view your flight schedule before you leave and get real-time alerts about any changes.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN) route, aim to travel before 3 PM. Flights after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Waynesville from O'Hare Intl. Airport (ORD)?
If you’ve booked a direct flight from O’Hare Intl. Airport (ORD) to Waynesville, Waynesville Regional Airport (TBN) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN) last-minute?
Booking your plane ticket from ORD to TBN right before your journey is typically more expensive. However, if you’re flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book an ORD to TBN flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to TBN flight and hotel package with Expedia could lead to significant savings. What’s more, managing everything in one place will take the hassle out of planning your trip. Just pick your flights and choose from our extensive range of stays, then personalize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Waynesville Regional Airport (TBN)?
In most cases, you can reschedule or cancel your ORD to TBN flight. However, there may be additional charges, especially if you made your booking over 24 hours ago. Check your itinerary for the airline’s fees and guidelines on flight changes, or if you want further information, visit our Customer Service portal.

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*Available to One Key members.