Cheap flights from Lexington to Chicago

One-way fares from $116 · LEX → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Lexington
Cheapest fare
$116

American Airlines · Fri, Nov 13

Cheapest month
November

from $116

Direct flights
Yes

American Airlines

Flight time
1h 45m

500 km

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Cheapest month to fly from Lexington to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $116

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

American Airlines
Depart05:14 Fri, Nov 13LEX → ORD 1h 45m · Direct
$116one way, per person
View deal
See every date in November 2026 →

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About flights from Lexington to Chicago

Lexington (LEX) and Chicago (CHI) are about 500 km apart. Direct flights take around 1h 45m, and recent direct fares were with American Airlines. Over the next few months, one-way fares start from $116, 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 Lexington to Chicago?

The cheapest one-way fare we've seen recently is $116 with American Airlines, departing Friday, November 13, 2026.

What is the cheapest month to fly from Lexington to Chicago?

November 2026 currently has the lowest fares, from $116 one way.

Are there direct flights from Lexington to Chicago?

Yes. Recent direct fares were with American Airlines.

How long is the flight from Lexington to Chicago?

A direct flight takes about 1h 45m. Lexington and Chicago are around 500 km apart.

Which airlines fly from Lexington to Chicago?

Recent fares on this route were with American Airlines.

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