CHI to TBN, to Waynesville St. Robert Regional Airport Cheap Flights

Based on HopeGoo data, Contour Airlines offers one-way fares as low as US$82 on Cheapest nonstop routes (e.g. ORD to TBN on Thu, Apr 2), while Contour Airlines offers Cheapest nonstop round-trips from US$131 departing on Sun, Feb 15 and returning on Sun, Feb 22.

It takes about 1 hour 45 minutes to fly from Chicago to Fort Leonard Wood.

By analyzing data from all airlines on the HopeGoo flight calendar, it looks like the best time to book a flight from Chicago to Fort Leonard Wood is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

To find best deals on flights from Chicago to Fort Leonard Wood, you can use various tools on HopeGoo: · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Thu, Apr 2, with one-way flights priced at just US$82. · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Contour Airlines. · Set up price alerts to easily monitor ticket prices without having to check every day. · Check HopeGoo flight deals and promo codes frequently. · Avoid peak season unless you book very early. It seems the peak season for Fort Leonard Wood travel is around November. · Get exclusive promo codes for HopeGoo app users.

The cheapest months to fly from Chicago to Fort Leonard Wood is September, when demand for travel is lower.

After crunching the numbers on our February flight calendar, it's currently cheapest to fly from Chicago to Fort Leonard Wood on February 18, 2026 with Contour Airlines, with prices starting at US$131.

The time difference between Fort Leonard Wood and Chicago is 0h.

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