American AirlinesDepart21:15
Fri, Nov 13ORD → LEX
1h 33m · Direct
$94one way, per person
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- Cheapest fare
- $94
- Cheapest month
- November
- Direct flights
- Yes
- Flight time
- 1h 33m
American Airlines · Fri, Nov 13
from $94
American Airlines and United Airlines
500 km
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Cheapest month to fly from Chicago to Lexington
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in November 2026
The lowest fares we've seen for each day, cheapest first.
American Airlines
United AirlinesDepart07:40
Sun, Nov 8ORD → LEX
1h 33m · Direct
$231one way, per person
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About flights from Chicago to Lexington
Chicago (CHI) and Lexington (LEX) are about 500 km apart. Direct flights take around 1h 33m, and recent direct fares were with American Airlines and United Airlines. Over the next few months, one-way fares start from $94, and November 2026 is currently the cheapest month to fly.
These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
How much is a flight from Chicago to Lexington?
The cheapest one-way fare we've seen recently is $94 with American Airlines, departing Friday, November 13, 2026.
What is the cheapest month to fly from Chicago to Lexington?
November 2026 currently has the lowest fares, from $94 one way.
Are there direct flights from Chicago to Lexington?
Yes. Recent direct fares were with American Airlines and United Airlines.
How long is the flight from Chicago to Lexington?
A direct flight takes about 1h 33m. Chicago and Lexington are around 500 km apart.
Which airlines fly from Chicago to Lexington?
Recent fares on this route were with American Airlines and United Airlines.
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