Cheap flights from Nashville to Chicago from $129

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 $366. 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 $670.

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 $352. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,023.

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 $268 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 $180 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 June 2026, prices for Nashville to Chicago flights are approximately 57% more expensive when compared to flights at the same time last year.

Allegiant Air, Southwest, and United Airlines 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 30% 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.

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $176.

Flights connecting via Quincy (UIN) have the shortest average one-way travel time: 3h 30m.

Quincy (UIN) has the shortest average layover time for this route: 0h 45m.

As of June 2026, there are 50 flights per day flying from Nashville to Chicago. The most common time of day flights depart is 10:00AM, with 56% of flights taking off at noon.

As of June 2026, 350 flights take off from Nashville and land in Chicago each week. The most common flight departure day for this route is Tue, with 21% of weekly flights taking off on this day.