$147 Find Cheap Flights from Lexington to Chicago - Compare and Save

Among airlines operating Lexington to Chicago flights:

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

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

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

• United Airlines
• American Airlines

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

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 Lexington to Chicago:

• Economy Class
• Business Class
• First Class

On this route, nonstop and layover fares are close on average, with nonstop at $291 round-trip and layover options via Atlanta Hartsfield-Jackson (ATL) at $298.

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.

One-stop flights from Lexington to Chicago most commonly connect through:

• Chicago O'Hare Intl (ORD) - 64% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 18% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 9% of one-stop connections
• Charlotte Douglas (CLT) - 9% of one-stop connections

Chicago O'Hare Intl (ORD) handles the largest share of one-stop connections on this route.

On the Lexington to Chicago route, being flexible with your departure day can save you up to 43%. Saturday is the cheapest day at $263 round-trip on average, while Sunday is the most expensive at $461: a $198 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Morning is the busiest departure period on Lexington to Chicago flights, with 63% of flights leaving in that window. Evening departures account for 25%, afternoon flights for 12%, and night flights for 0%.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

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

• Earliest: departs at 5:00 am and lands at 6:49 am
• Latest: departs at 10:10 pm and lands at 11:59 pm.

The flight takes about 1h 49m.

Last-minute fares on this route - booked within 2 weeks of departure - run 31% above the route average of $291. Book 25 weeks before departure for the lowest fares.

A nonstop flight from Lexington to Chicago takes 1h 49m, 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 $278 to $1,013. That means the highest observed fare was about 4x higher than the lowest one.

One-way fares from Lexington to Chicago are currently lower than usual. Average one-way flight prices are about $220, which is 26% below the typical average for this route.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 17m, compared with 4h 12m via Chicago O'Hare Intl (ORD) and 4h 33m via Atlanta Hartsfield-Jackson (ATL).

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

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Round-trip flights from Lexington to Chicago range from $249 to $381, with an average of $291 over the past 12 months. Anything below $249 counts as a good deal.

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