Cheap flights from Tennessee to Chicago from $66

The month of October is, on average, the cheapest month to fly to Chicago from Tennessee, with most prices found around $272. If you’re not able to fly to Chicago in October, then November is your next best option. Flight prices from Tennessee to Chicago during November average around $275.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $417. 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 Tennessee to Chicago for around $806.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Tennessee to Chicago during this time can be as low as $401. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,034.

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

You are more likely to see cheaper flights to Chicago from Tennessee when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $310 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Tennessee for as low as $238 on momondo.

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

Allegiant Air, Southwest, and United Airlines are the most popular carriers operating from Tennessee to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Tennessee according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of September 2026, 117 flights take off from Tennessee and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 44% of daily flights taking off at noon.

The number of flights available between Tennessee and Chicago is 825 per week as of September 2026. The most frequent departure day is Fri, with 19% of weekly flights leaving on this day.