Cheap flights from Lexington to Chicago from $131

The month of February is, on average, the cheapest month to fly to Chicago from Lexington, with most prices found around $238. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Lexington to Chicago during October average around $249.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $426. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Lexington to Chicago for around $803.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Lexington to Chicago during this time can be as low as $519. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $786.

Fly from Lexington Blue Grass to Chicago O'Hare Intl for the best Lexington Blue Grass - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Lexington when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $293 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Lexington for as low as $189 on momondo.

There are 4 cabin classes available to choose from on Lexington to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Delta, United Airlines, and Allegiant Air are the most popular carriers operating from Lexington Blue Grass to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Lexington according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

The number of flights available between Lexington and Chicago is 20 per day as of July 2026. The most frequent departure time is 5:00AM, with 36% of daily flights leaving in the afternoon.

The number of flights available between Lexington and Chicago is 144 per week as of July 2026. The most frequent departure day is Thu, with 19% of weekly flights leaving on this day.