Cheap flights from Nashville to Chicago from $135

The month of November is, on average, the cheapest month to fly to Chicago from Nashville, with most prices found around $34. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Nashville to Chicago during October average around $36.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $335. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Nashville to Chicago for around $685.

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 $326. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $949.

Fly from Nashville Intl to Chicago Midway 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 $241 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 $138 on momondo.

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

As of May 2026, prices for Nashville to Chicago flights are approximately 82% more expensive when compared to flights at the same time last year.

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

American Airlines, United Airlines and Southwest 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 33% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 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 71 flights per day flying from Nashville to Chicago. The most common time of day flights depart is 2:00PM, with 44% of flights taking off in the afternoon.

As of May 2026, 503 flights take off from Nashville and land in Chicago each week. The most common flight departure day for this route is Wed, with 16% of weekly flights taking off on this day.