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Fort Leonard Wood

Cheap flights from Chicago (CHI) to Fort Leonard Wood (TBN)

CHI — TBN
May 2 — May 91
Sat 5/2
Sat 5/9
1 adult, Economy
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Find flight deals from Chicago to Fort Leonard Wood

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Fort Leonard Wood (TBN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Good round-trip deal

$153 or less
Provider with most accurate pricing for Chicago (CHI)-Fort Leonard Wood Waynesville Regional flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Fort Leonard Wood Waynesville Regional flights.
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Price to beat on a round-trip flight from Chicago (CHI) to Fort Leonard Wood Waynesville Regional.
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  • Most accurate provider: When it comes to deals on Chicago-Fort Leonard Wood flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Fort Leonard Wood flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Fort Leonard Wood flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Fort Leonard Wood flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Fort Leonard Wood flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Fort Leonard Wood

Have a flexible travel schedule? Discover the best time to fly to Fort Leonard Wood from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Fort Leonard Wood

What is the cheapest month to book a flight from Chicago to Fort Leonard Wood?

Currently, July is the cheapest month in which you can book a flight from Chicago to Fort Leonard Wood (average of $163). Flying from Chicago to Fort Leonard Wood in August is currently the most expensive (average of $219). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to TBN?

Find hourly flight availability from Chicago to Fort Leonard Wood. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 2, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Fort Leonard Wood as you normally would.

Reviews of airlines servicing Fort Leonard Wood

Get insights into the airlines that provide service to Fort Leonard Wood. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Fort Leonard Wood. Reviews last updated April 2, 2026.
See what other customers who have flown with Contour from Chicago to Fort Leonard Wood have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Contour
7.6
Good
42 reviews

Comfort

7.3

Overall

7.6

Boarding

7.6

Crew

7.9

Food

6.8

Entertainment

6.1

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo
Contour
7.6
Good
42 reviews
Contour
7.6
Good
42 reviews

Comfort

7.3

Overall

7.6

Boarding

7.6

Crew

7.9

Food

6.8

Entertainment

6.1

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo

Related info for your journey

Find useful and relevant information for your journey from Chicago to Fort Leonard Wood. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Fort Leonard Wood from Chicago?

    Fort Leonard Wood Waynesville Regional (TBN) is the airport you will fly into if you book a flight from Chicago to Fort Leonard Wood. You should not have trouble finding flights to Waynesville Regional from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Fort Leonard Wood airport from Chicago. It is only a 2.6 mi journey from Waynesville Regional (TBN) to Fort Leonard Wood’s city center.

  • Can I find deals for flights from Chicago to Fort Leonard Wood that include hotel bookings?

    Yes. In addition to deals on Chicago to Fort Leonard Wood flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Fort Leonard Wood?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Fort Leonard Wood.

  • Can I find deals for business class flights from Chicago to Fort Leonard Wood?

    Yes. Cheapflights offers flight deals from Chicago to Fort Leonard Wood by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Fort Leonard Wood?

    Currently, July is the cheapest month in which you can book a flight from Chicago to Fort Leonard Wood (average of $163). Flying from Chicago to Fort Leonard Wood in August is currently the most expensive (average of $219). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Fort Leonard Wood?

Book flights to Fort Leonard Wood if you plan to visit one of these locations
Rolla
Osage Beach
Lake Ozark

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