Cheap flights from Nashville to Chicago from $109

The month of October is, on average, the cheapest month to fly to Chicago from Nashville, with most prices found around $175. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Nashville to Chicago during September average around $206.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $405. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Nashville to Chicago for around $745.

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 $390. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,028.

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 $296 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 $231 on momondo.

There are 4 cabin classes available to choose from on Nashville 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 August 2026, prices for Nashville to Chicago flights are approximately 94% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Nashville according to our data. United Airlines is the first choice among our users, with 37% 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 August 2026, there are 63 flights per day flying from Nashville to Chicago. The most common time of day flights depart is 7:00AM, with 44% of flights taking off at noon.

As of August 2026, 443 flights take off from Nashville and land in Chicago each week. The most common flight departure day for this route is Fri, with 16% of weekly flights taking off on this day.