$140 Find Cheap Flights from Chicago to Lexington - Compare and Save

Among airlines operating Chicago to Lexington flights:

• United Airlines: offers extra legroom; offers free seat selection
• American Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

2 airlines operate flights between Chicago and Lexington. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flights from Chicago to Lexington may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Lexington Blue Grass (LEX).

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in Economy Class
• American Airlines: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Three cabin classes are available on flights from Chicago to Lexington:

• Economy Class
• Business Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $187 round-trip via Chicago O'Hare Intl (ORD), compared to $347 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Connecting flights from Chicago to Lexington most commonly pass through:

• Detroit Metropolitan Wayne County (DTW) - 67% of one-stop connections
• Chicago O'Hare Intl (ORD) - 33% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

On the Chicago to Lexington route, being flexible with your departure day can save you up to 44%. Saturday is the cheapest day at $264 round-trip on average, while Monday is the most expensive at $468: a $204 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Morning is the busiest departure period on Chicago to Lexington flights, with 38% of flights leaving in that window. Afternoon departures account for 25%, night flights for 25%, and evening flights for 12%.

These are the earliest and latest flight times available from Chicago to Lexington:

• Earliest: departs at 6:50 am and lands at 8:27 am
• Latest: departs at 11:55 pm and lands at 1:32 am.

The flight takes about 1h 37m.

Last-minute fares on this route - booked within 2 weeks of departure - run 27% above the route average of $347. Book 17 weeks before departure for the lowest fares.

A nonstop flight from Chicago to Lexington takes 1h 37m, covering 310 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $279 to $925. That means the highest observed fare was about 3x higher than the lowest one.

One-way fares from Chicago to Lexington are currently lower than usual. Average one-way flight prices are about $188, which is 41% below the typical average for this route.

Flying via Chicago O'Hare Intl (ORD) gives the shortest average 1-stop total travel time at 4h 10m, compared with 5h 48m via Detroit Metropolitan Wayne County (DTW).

Lexington is 1 hour ahead of Chicago (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Lexington Blue Grass Airport (LEX) hosts 5 major car rental companies, with daily rates starting from around $30 for economy cars. Top options include:
• Dollar
• Hertz
• Alamo
• Budget
• Enterprise Rent-A-Car

Round-trip flights from Chicago to Lexington range from $253 to $464, with an average of $347 over the past 12 months. Anything below $253 counts as a good deal.

American Airlines is the only airline on the Chicago to Lexington route offering in-flight Wi-Fi. Pricing depends on fare class.