Cheap flights from Fort Myers to Chicago from $142

The month of February is, on average, the cheapest month to fly to Chicago from Fort Myers, with most prices found around $193. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Fort Myers to Chicago during January average around $197.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $361. 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 Fort Myers to Chicago for around $497.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Fort Myers to Chicago during this time can be as low as $343. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $406.

Fly from Fort Myers SW Florida Intl to Chicago Midway for the best Fort Myers SW Florida Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Fort Myers when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $272 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Fort Myers for as low as $240 on momondo.

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

You could potentially save up to 7% on your flight if you consider stops on a Fort Myers to Chicago flight.

As of August 2026, prices for Fort Myers to Chicago flights are approximately 49% more expensive when compared to flights at the same time last year.

Southwest, Frontier, and JetBlue are the most popular carriers operating from Fort Myers SW Florida Intl to Chicago

United Airlines, American Airlines and Allegiant Air are the top three most popular airlines that fly to Chicago from Fort Myers according to our data. United Airlines is the first choice among our users, with 48% 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.

The number of flights available between Fort Myers and Chicago is 14 per day as of August 2026. The most frequent departure time is 4:00PM, with 51% of daily flights leaving at noon.

As of August 2026, 101 flights take off from Fort Myers and land in Chicago each week. The most common flight departure day for this route is Tue, with 19% of weekly flights taking off on this day.