Cheap flights from Chicago to Fort Myers from $140

In general, January 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 $225. If you are unable to visit Fort Myers during the month of January, then departing from Chicago during the month February is also very affordable. Most momondo users find prices during this month for around $238.

The cheapest day to depart from Chicago to Fort Myers is on a Wednesday when prices can be found for as low as $299. Flights from Chicago to Fort Myers on a Sunday will generally be more expensive and average around $363. 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 morning when flights can be purchased for as low as $322. Flights in the evening are often more expensive with an average ticket price of $372.

Fly from Chicago O'Hare Intl 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 $308 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 $267 on momondo.

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

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

United Airlines, Allegiant Air and American Airlines 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 35% of people opting to fly with this airline when traveling to Fort Myers. Keep in mind that there are 7 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 21% 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.

Thursday 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 August 2026, 13 flights take off from Chicago and land in Fort Myers each day. The most common flight departure time for this route is 7:00AM, with 73% of daily flights taking off at noon.

97 flights are operational weekly from Chicago to Fort Myers as of August 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.