$263 Cheap Flights from Fort Leonard Wood (TBN) to Chicago (ORD)

Bundle Your Flight + Hotel & Save!

    Plan, book, fly with confidence
  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash

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

Prices were available within the past 7 days and start at $263 for one-way flights and $525 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Contour Airlines
Contour Airlines
Contour Airlines
Contour Airlines
Contour Airlines
Contour Airlines
Contour Airlines
Contour Airlines
Contour Airlines
Flights from Fort Leonard Wood (TBN) to Chicago (ORD)
Origin airport
St. Robert Regional
Destination airport
O'Hare Intl.
Roundtrip price
$525
Distance
369 mi

Fort Leonard Wood to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Fort Leonard Wood to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Fort Leonard Wood to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is $263 now!

Frequently asked questions

Is it cheaper to buy a plane ticket from Waynesville Regional Airport (TBN) to ORD last minute?
Booking your trip from TBN to ORD at the last minute could save you some dough if you’re lucky to find a terrific deal. However, tickets usually don’t get cheaper as the departure date nears. If you wait around, flights could also be sold out or the best seats gone (because no one wants the middle seat). If you’d rather play it safe, book well ahead of the date you want to leave. Remember that some of the most awesome deals can be found up to a year in advance. If your favorite carrier hasn’t released its airfares yet, check back regularly as deals are updated on Expedia constantly.
What airports do you fly into for Chicago from Rolla?
From Rolla, you can fly into Chicago via O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT). Research which terminal is right for you before making your decision. If you decide to land at O’Hare Intl. Airport (ORD), it’s roughly 16 mi northwest of the center of the city. Use the money you save when booking your ticket with Expedia to explore the city’s popular sights, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from Waynesville Regional Airport (TBN) to O'Hare Airport?
You can make changes to your Waynesville Regional Airport (TBN) to ORD ticket by logging in to the Expedia Trips portal. But before you begin, read over the rules and restrictions in your itinerary to see what you can do and if any charges apply. Some carriers have a change fee per person, in addition to any difference in fares. But if you booked in the last 24 hours, you may be able to cancel for free and arrange new flights. You can also head to our Customer Service portal for more advice and to chat with our Virtual Agent.
*Available to One Key members.