Private charter · MDW → LEX
Chicago to Lexington
308 miles, about 1 hr 45 min in a Cirrus SR20. One price for the whole airplane.
Price your flight from Chicago to Lexington
The trip
Chicago to Lexington, door to door faster.
Trade about 7 hours on the road for about 1 hr 45 min in the air. Littlebird flies you direct from Chicago Midway International Airport in Chicago to Blue Grass Airport in Lexington, 308 miles in a Cirrus SR20. You get the whole airplane for one price, with every fee and tax shown before you book.
- Distance
- 308 mi
- Flight
- 1 hr 45 min
- Driving
- 7 hours
- Passengers
- Up to 5
Flight time by aircraft
- Cirrus SR20 · up to 3 passengers1 hr 45 min
- Cirrus Vision Jet · up to 5 passengers55 min
Planned times in the air. Your quote shows exact departure and arrival times.
Departing Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
KIGQ
Regional airportLansing Municipal Airport
Chicago
- From downtown
- 25 mi
- Longest runway
- 4,002 ft
K05C
Regional airportGriffith-Merrillville Airport
Griffith
- From downtown
- 28 mi
- Longest runway
- 4,900 ft
Arriving Lexington
Airports in Lexington
LEX
Commercial airportBlue Grass Airport
Lexington · KLEX
- From downtown
- 6 mi
- Longest runway
- 7,004 ft
FFT
Regional airportCapital City Airport
Frankfort · KFFT
- From downtown
- 24 mi
- Longest runway
- 5,006 ft
KIOB
Regional airportMount Sterling Montgomery County Airport
Mount Sterling
- From downtown
- 28 mi
- Longest runway
- 5,000 ft
K27K
Regional airportGeorgetown-Scott County Regional Airport
Georgetown
- From downtown
- 13 mi
- Longest runway
- 5,498 ft
K0I8
Regional airportCynthiana-Harrison County Airport
Cynthiana
- From downtown
- 25 mi
- Longest runway
- 3,850 ft
When you land
Things to do in Lexington
Lexington sits at the heart of the Bluegrass region, where limestone-rich soil has nurtured some of the world’s finest thoroughbreds for more than two centuries. Hundreds of horse farms surround the city, and Keeneland’s race meets and horse auctions bring owners, breeders and buyers from around the world. The University of Kentucky and UK HealthCare are the city’s largest employers, Toyota’s largest manufacturing plant anywhere is in nearby Georgetown, and the region’s bourbon distilleries add both industry and tourism.
- 01
Keeneland
This historic racetrack holds race meets in April and October and some of the world’s most important thoroughbred auctions, and visitors can watch morning workouts on the training track.
- 02
Kentucky Horse Park
A working horse farm and equestrian center north of town, the park includes the International Museum of the Horse, daily breed presentations and the grave of Man o’ War.
- 03
Horse Farm Tours
Guided tours take visitors behind the stone fences of famous thoroughbred farms to see retired champions and stallions, with tours booked through local operators and individual farms.
- 04
Woodford Reserve Distillery
Near Versailles, this National Historic Landmark distillery offers tours of its limestone buildings and copper pot stills set among horse country.
- 05
Ashland, the Henry Clay Estate
The home of the 19th-century statesman, rebuilt by his son on the original foundations, is open for tours and surrounded by gardens and wooded grounds.
- 06
Shaker Village of Pleasant Hill
About 30 miles southwest near Harrodsburg, the restored 19th-century Shaker community offers overnight lodging, a farm-to-table restaurant, trails and riverboat rides on the Kentucky River.
Questions
Chicago to Lexington flights
How long is a private flight from Chicago to Lexington?
About 1 hr 45 min in a Cirrus SR20, for 308 miles direct. Driving the same trip takes about 7 hours.
Which airports do flights from Chicago to Lexington use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Blue Grass Airport (LEX), Capital City Airport (FFT), or Mount Sterling Montgomery County Airport (KIOB). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Lexington cost?
The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.
Can I book a round trip between Chicago and Lexington?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Lexington back to Chicago are priced the same way.
Return flight
Lexington to Chicago
More flights from Chicago
More flights to Lexington
Explore Chicago private charter and Lexington private charter, airports and things to do. Arriving at Blue Grass Airport (LEX).
Chicago to Lexington, on your schedule
Choose your departure time and see an instant price for the whole airplane. Bring up to 5 passengers for the same price.
Get an instant price