Cheap flights from Chicago to Fort Myers from $67

In general, August is the cheapest month to fly from Chicago to Fort Myers. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $188. If you are unable to visit Fort Myers during the month of August, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $191.

The cheapest day to depart from Chicago to Fort Myers is on a Tuesday when prices can be found for as low as $255. Flights from Chicago to Fort Myers on a Sunday will generally be more expensive and average around $297. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

The cheapest time of day to fly to Fort Myers is in the afternoon when flights can be purchased for as low as $268. Flights at noon are often more expensive with an average ticket price of $294.

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

You are more likely to see cheaper flights to Fort Myers from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Fort Myers for around $264 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Fort Myers from Chicago for as low as $227 on momondo.

There are 4 cabin classes available to choose from on Chicago to Fort Myers SW Florida Intl 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 Chicago to Fort Myers.

As of April 2026, prices for Chicago to Fort Myers flights are approximately 33% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Allegiant Air are the top three most popular airlines that fly to Fort Myers from Chicago according to our data. United Airlines is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Fort Myers. Keep in mind that there are 8 different airlines that fly to Fort Myers on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% of flights between Chicago and Fort Myers have experienced a delay on any given week. The average delay length over the past 12 months has been 148 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 15% of their flights experiencing any sort of delay.

As of April 2026, 25 flights take off from Chicago and land in Fort Myers each day. The most common flight departure time for this route is 10:00AM, with 49% of daily flights taking off at noon.

176 flights are operational weekly from Chicago to Fort Myers as of April 2026. The most popular departure day for this route is Sun, with 16% of flights per week taking off on this day.