Cheap flights from Fort Myers to Chicago from $104

The month of September is, on average, the cheapest month to fly to Chicago from Fort Myers, with most prices found around $30. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Fort Myers to Chicago during January 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 $284. 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 $426.

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 $190. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $371.

Fly from Fort Myers SW Florida Intl to Chicago O'Hare Intl 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 $238 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 $188 on momondo.

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

As of May 2026, prices for Fort Myers to Chicago flights are approximately 144% more expensive when compared to flights at the same time last year.

United Airlines, Southwest, and Delta are the most popular carriers operating from Fort Myers SW Florida Intl to Chicago

United Airlines, American Airlines and Spirit Airlines 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 38% 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 21 per day as of May 2026. The most frequent departure time is 11:00AM, with 45% of daily flights leaving in the afternoon.

As of May 2026, 151 flights take off from Fort Myers and land in Chicago each week. The most common flight departure day for this route is Fri, with 17% of weekly flights taking off on this day.