Is there a direct flight from Chicago to Fort Leonard Wood?

Yes — you can fly nonstop from Chicago (ORD) to Fort Leonard Wood (TBN) on Contour.

Which airlines fly nonstop from Chicago to Fort Leonard Wood?

Contour flies nonstop between Chicago (ORD) and Fort Leonard Wood (TBN).

There is about 1 nonstop departure per day (roughly 7 per week) from Chicago to Fort Leonard Wood.

Fort Leonard Wood is about 369 miles from Chicago by air.

Popular things to do include Ozark Caverns, Lake of the Ozarks State Park, Montauk State Park, Gourd Creek Cave, and more.

Fort Leonard Wood · Missouri

Nonstop service from ORD to TBN on Contour. Here's the schedule at a glance — plus what to do once you land.

Airlines

Contour

Nonstop flights

~1/day

Distance

369 mi

Flight time

~1h 15mgate to gate

Elevation

1,159 ft479 ft higher than your departure

Days operated

Daily (all week)

This is a rare nonstop: only 2 cities fly direct to Fort Leonard Wood, and Chicago is one of them. From anywhere else you'd be connecting.

1h 15m in the air, 369 miles: short enough that a single night in Fort Leonard Wood is worth it, and a day trip is not absurd.

St. Robert, a city of 5,200 (2020) city in Central Missouri, is a gateway community to the US Army base at Fort Leonard Wood.

Summary from Wikivoyage (CC BY-SA).

Ozark Caverns
Ozark Caverns is an unlit cave located within the south side of Lake of the Ozarks State Park. It is part of a large group of "wild" caves in Missouri.
Lake of the Ozarks State Park
Lake of the Ozarks State Park is a public recreation area on the Grand Glaize Arm of the Lake of the Ozarks; it is the largest state park in Missouri.
Montauk State Park
Montauk State Park is a public recreation area occupying nearly 3,000 acres (1,200 ha) at the headwaters of the Current River, fifteen miles (24 km) southwest of Salem, Missouri.
Gourd Creek Cave
The Gourd Creek Cave is an archaeological site in Phelps County in the Ozarks of Missouri, United States.

Attraction descriptions from Wikipedia (CC BY-SA); place data from Wikidata (CC0).

How long to stay: A long weekend is plenty of time to see Fort Leonard Wood, including Ozark Caverns, Lake of the Ozarks State Park, and Montauk State Park.

Is there a direct flight from Chicago to Fort Leonard Wood?: Yes — you can fly nonstop from Chicago (ORD) to Fort Leonard Wood (TBN) on Contour.
Which airlines fly nonstop from Chicago to Fort Leonard Wood?: Contour flies nonstop between Chicago (ORD) and Fort Leonard Wood (TBN).
How many nonstop flights are there from Chicago to Fort Leonard Wood?: There is about 1 nonstop departure per day (roughly 7 per week) from Chicago to Fort Leonard Wood.
How far is Fort Leonard Wood from Chicago?: Fort Leonard Wood is about 369 miles from Chicago by air.
What is there to do in Fort Leonard Wood?: Popular things to do include Ozark Caverns, Lake of the Ozarks State Park, Montauk State Park, Gourd Creek Cave, and more.

The closest other departure airports to Chicago — each opens up more nonstop destinations.