Cheap flights from Louisville to Chicago from $89

The month of November is, on average, the cheapest month to fly to Chicago from Louisville, with most prices found around $196. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Louisville to Chicago during October average around $225.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $501. 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 $656.

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 $492. 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 O'Hare Intl 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 $276 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 $141 on momondo.

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

You could potentially save up to 45% on your flight if you consider stops on a Louisville to Chicago flight.

As of March 2026, prices for Louisville to Chicago flights are approximately 24% cheaper when compared to flights at the same time last year.

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

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Louisville according to our data. American Airlines is the first choice among our users, with 43% 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 March 2026, there are 19 flights per day flying from Louisville to Chicago. The most common time of day flights depart is 7:00AM, with 48% of flights taking off at noon.

134 flights are operational weekly from Louisville to Chicago as of March 2026. The most popular departure day for this route is Sat, with 25% of flights per week taking off on this day.