How to get from Chicago to Lexington: connecting flights, about 5h 50m total

Flights from Chicago to Lexington

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Best fares from Chicago to Lexington

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $91 19 November 2026, nonstop Cheapest nonstop $91 19 November 2026, AA Cheapest month November 2026 tickets from $91

Where to connect

Options with one connection, fastest first

fastest, via Detroit: 5h 50m
connection option: 1
straight-line distance: 313 mi (504 km)

fastest

Via Detroit

5h 50m

with the connection

Chicago to Detroit flight 1h 28m

Connection of about 3h

Detroit to Lexington flight 1h 22m

One ticket or two

How the options are calculated and what to keep in mind at the connection

Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.

Nearest nonstop flights

The closest you can get without a connection

From Chicago to cities closest to Lexington

Chicago to Louisville Louisville: 70 mi (113 km) from Lexington, flight 1h 30m from $218 Chicago to Indianapolis Indianapolis: 150 mi (241 km) from Lexington, flight 1h 11m from $77 Chicago to Columbus Columbus: 155 mi (250 km) from Lexington, flight 1h 31m from $92 Chicago to Nashville Nashville: 180 mi (290 km) from Lexington, flight 1h 42m from $45 Chicago to Charlotte Charlotte: 280 mi (451 km) from Lexington, flight 2h 6m from $114 Chicago to Cleveland Cleveland: 282 mi (454 km) from Lexington, flight 1h 31m from $117

To Lexington from cities closest to Chicago

Detroit to Lexington Detroit: 237 mi (381 km) from Chicago, flight 1h 22m Charlotte to Lexington Charlotte: 587 mi (945 km) from Chicago, flight 1h 29m from $94 Atlanta to Lexington Atlanta: 589 mi (948 km) from Chicago, flight 1h 15m New York to Lexington New York: 711 mi (1,144 km) from Chicago, flight 2h 18m from $205 Orlando to Lexington Orlando: 986 mi (1,587 km) from Chicago, flight 2h 4m from $78

Frequently asked questions

Is there a nonstop flight from Chicago to Lexington?

There are no nonstop flights in the schedule. You will need a connection, the fastest is via Detroit.

What is the fastest way to fly from Chicago to Lexington?

Via Detroit: 1h 28m to the connection, 1h 22m after it, about 5h 50m in total with 3h for the connection.

How far is Lexington from Chicago?

313 mi (504 km) in a straight line between the cities.

How much time should I allow for the connection?

The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.