Cheap flights from Chicago Midway Airport to Fort Myers from $137

In general, January is the cheapest month to fly from Chicago Midway Airport to Fort Myers. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $278. If you are unable to visit Fort Myers during the month of January, then departing from Chicago Midway Airport during the month September is also very affordable. Most momondo users find prices during this month for around $315.

The cheapest day to depart from Chicago Midway Airport to Fort Myers is on a Wednesday when prices can be found for as low as $330. Flights from Chicago Midway Airport to Fort Myers on a Sunday will generally be more expensive and average around $388. 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 $347. Flights in the evening are often more expensive with an average ticket price of $376.

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

You are more likely to see cheaper flights to Fort Myers from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Fort Myers for around $390 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 Midway Airport for as low as $309 on momondo.

There is only 1 cabin class available to choose from on Chicago Midway Airport to Fort Myers 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 11% on your flight if you consider stops on a Chicago Midway Airport to Fort Myers flight.

As of November 2026, prices for Chicago Midway Airport to Fort Myers flights are approximately 10% cheaper when compared to flights at the same time last year.

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

Southwest, Allegiant Air and Delta are the top three most popular airlines that fly to Fort Myers from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 80% of people opting to fly with this airline when traveling to Fort Myers. Keep in mind that there are 3 different airlines that fly to Fort Myers on a routine basis, so you have a few additional options to choose from.

1 flights are operational daily from Chicago Midway Airport to Fort Myers as of November 2026. The most popular departure time for this route is 5:00AM, with 40% of flights per day taking off in the afternoon.

As of November 2026, there are 13 flights per week flying from Chicago Midway Airport to Fort Myers. The most common day of the week flights depart is Mon, with 31% of flights taking off on this day.