Cheap flights from Nashville to Chicago from $109

The month of September is, on average, the cheapest month to fly to Chicago from Nashville, with most prices found around $127. If you’re not able to fly to Chicago in September, then July is your next best option. Flight prices from Nashville to Chicago during July average around $145.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $312. 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 Nashville to Chicago for around $783.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Nashville to Chicago during this time can be as low as $387. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $664.

Fly from Nashville Intl to Chicago Greater Rockford for the best Nashville Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Nashville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $215 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Nashville for as low as $117 on momondo.

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

No. A direct flight is the cheapest option for a flight between Nashville to Chicago.

As of February 2026, prices for Nashville to Chicago flights are approximately 33% cheaper when compared to flights at the same time last year.

Delta, Southwest, and United Airlines are the most popular carriers operating from Nashville Intl to Chicago

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from Nashville according to our data. American Airlines is the first choice among our users, with 32% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of February 2026, there are 45 flights per day flying from Nashville to Chicago. The most common time of day flights depart is 2:00PM, with 55% of flights taking off in the afternoon.

As of February 2026, 316 flights take off from Nashville and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.