Cheap flights from Louisville to Chicago from $101

The month of January is, on average, the cheapest month to fly to Chicago from Louisville, with most prices found around $67. If you’re not able to fly to Chicago in January, then December is your next best option. Flight prices from Louisville to Chicago during December average around $77.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $489. 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 Louisville to Chicago for around $630.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Louisville to Chicago during this time can be as low as $486. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $874.

Fly from Louisville Intl to Chicago Midway for the best Louisville Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Louisville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $295 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Louisville for as low as $95 on momondo.

You could potentially save up to 61% on your flight if you consider stops on a Louisville to Chicago flight.

As of May 2026, prices for Louisville to Chicago flights are approximately 103% more expensive when compared to flights at the same time last year.

American Airlines, Southwest, and Delta are the most popular carriers operating from Louisville Intl to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Louisville according to our data. United Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of May 2026, there are 39 flights per day flying from Louisville to Chicago. The most common time of day flights depart is 7:00PM, with 57% of flights taking off at noon.

275 flights are operational weekly from Louisville to Chicago as of May 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.