$235+ Cheap flights from Midway (MDW) to Fort Leonard Wood (TBN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — TBN
Dec 9 — Dec 161
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Fort Leonard Wood with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Fort Leonard Wood
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to Fort Leonard WoodExplore the most affordable flight options available from Midway to Fort Leonard Wood. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 9, 2026.
Explore the most affordable flight options available from Midway to Fort Leonard Wood. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:20 pm -
1 stop23h 25m
Mon 11/234:15 pm -
2 stops15h 59m
Deal found 11/4![Multiple Airlines logo]()
$613
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:51 am -
1 stop26h 54m
Wed 11/254:15 pm -
2 stops15h 59m
Deal found 11/6![Multiple Airlines logo]()
$688
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:28 am -
1 stop27h 17m
Fri 11/271:05 pm -
1 stop18h 32m
Deal found 11/8![Multiple Airlines logo]()
$719
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
2 stops15h 03m
Sat 11/284:15 pm -
2 stops15h 59m
Deal found 11/9![Multiple Airlines logo]()
$1,222
Best flights from Midway to Fort Leonard WoodDiscover carefully curated flight deals from Midway to Fort Leonard Wood that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 9, 2026.
Discover carefully curated flight deals from Midway to Fort Leonard Wood that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 9, 2026.
This Mytrip deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:20 pm -
3 stops27h 25m
Mon 11/234:15 pm -
2 stops15h 59m
Deal found 11/4![Multiple Airlines logo]()
$683
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:51 am -
1 stop26h 54m
Wed 11/254:15 pm -
2 stops15h 59m
Deal found 11/6![Multiple Airlines logo]()
$688
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:28 am -
1 stop27h 17m
Fri 11/271:05 pm -
1 stop18h 32m
Deal found 11/8![Multiple Airlines logo]()
$719
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
2 stops15h 03m
Sat 11/284:15 pm -
2 stops15h 59m
Deal found 11/9![Multiple Airlines logo]()
$1,222
Last-minute flights from Midway to Fort Leonard WoodDiscover last-minute flight deals from Midway to Fort Leonard Wood. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Fort Leonard Wood. Data last updated November 9, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
2 stops15h 03m
Wed 11/254:15 pm -
2 stops15h 59m
Deal found 11/6![Multiple Airlines logo]()
$688
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:28 am -
1 stop27h 17m
Fri 11/271:05 pm -
1 stop18h 32m
Deal found 11/8![Multiple Airlines logo]()
$719
This Mytrip deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
2 stops15h 03m
Sat 11/284:15 pm -
2 stops15h 59m
Deal found 11/9![Multiple Airlines logo]()
$1,222
One-way flights from Midway to Fort Leonard WoodSearch for one-way flight options from Midway to Fort Leonard Wood. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
Search for one-way flight options from Midway to Fort Leonard Wood. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This Mytrip deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:01 am -
1 stop5h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:11 pm -
2 stops22h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:08 am -
2 stops29h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$362
Find flight deals from Midway to Fort Leonard Wood
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $613 (Kiwi.com) |
One-way from | $235 (Mytrip) |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Fort Leonard Wood that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 9, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Fort Leonard Wood that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoFort Leonard Wood
MDW Chicago Midway - TBN Fort Leonard Wood Waynesville Regional
MDWTBN
Chicago Midway
Mon 12/21
6:01 am-11:45 am
1 stop5h 44m
Fort Leonard Wood Waynesville Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
ChicagoFort Leonard Wood
MDW Chicago Midway - TBN Fort Leonard Wood Waynesville Regional
MDWTBN
Chicago Midway
Tue 11/17
6:08 am-11:45 am
2 stops29h 37m
Fort Leonard Wood Waynesville Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$362
ChicagoFort Leonard Wood
MDW Chicago Midway - TBN Fort Leonard Wood Waynesville Regional
MDWTBN
Chicago Midway
Thu 11/19
12:20 pm-3:45 pm
3 stops27h 25m
Fort Leonard Wood Waynesville Regional
Mon 11/23
4:15 pm-8:14 am
2 stops15h 59m
$683
ChicagoFort Leonard Wood
MDW Chicago Midway - TBN Fort Leonard Wood Waynesville Regional
MDWTBN
Chicago Midway
Sat 11/21
8:51 am-11:45 am
1 stop26h 54m
Fort Leonard Wood Waynesville Regional
Wed 11/25
4:15 pm-8:14 am
2 stops15h 59m
$688
ChicagoFort Leonard Wood
MDW Chicago Midway - TBN Fort Leonard Wood Waynesville Regional
MDWTBN
Chicago Midway
Mon 11/23
8:28 am-11:45 am
1 stop27h 17m
Fort Leonard Wood Waynesville Regional
Fri 11/27
1:05 pm-7:37 am
1 stop18h 32m
$719
ChicagoFort Leonard Wood
MDW Chicago Midway - TBN Fort Leonard Wood Waynesville Regional
MDWTBN
Chicago Midway
Tue 11/24
8:42 pm-11:45 am
2 stops15h 03m
Fort Leonard Wood Waynesville Regional
Sat 11/28
4:15 pm-8:14 am
2 stops15h 59m
$1,222
Sorted by cheapest first
Compare providers for flights from Midway to Fort Leonard Wood
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Fort Leonard Wood in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-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 Midway Airport-Fort Leonard Wood flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Fort Leonard Wood flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-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 Midway Airport-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 Midway to Fort Leonard Wood
Have a flexible travel schedule? Discover the best time to fly to Fort Leonard Wood from Midway with our price prediction graph.
MDW-TBN
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.
Related info for your journey
Find useful and relevant information for your journey from Midway 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.
Traveling to a place near Fort Leonard Wood?
Book flights to Fort Leonard Wood if you plan to visit one of these locationsOsage Beach
Rolla
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