$149 Find Cheap Flights from Fort Myers to Chicago Midway Airport - Compare and Save

Among airlines operating Fort Myers to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Fort Myers and Chicago Midway Airport.

Flights from Fort Myers to Chicago Midway Airport usually depart from Fort Myers SW Florida Intl (RSW) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• JetBlue: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Fort Myers to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $337 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $359 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and American Airlines. Other aircraft seen on the route include Boeing 737 MAX 9 variants.

Most connecting flights from Fort Myers to Chicago Midway Airport pass through Atlanta Hartsfield-Jackson (ATL), which handles 100% of one-stop traffic on this route. Other layover airports each see under 5%.

Yes. Being flexible with your travel dates can save you up to 17% on the Fort Myers to Chicago Midway Airport route. Tuesday is the cheapest departure day at $326 round-trip on average, while Sunday is the most expensive at $392, a difference of $66. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Fort Myers to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from Fort Myers to Chicago Midway Airport:

• Earliest: departs at 5:50 am and lands at 8:44 am
• Latest: departs at 9:45 pm and lands at 12:39 am.

The flight takes about 2h 54m.

Last-minute fares on this route - booked within 2 weeks of departure - run 31% above the route average of $357. Book 24 weeks before departure for the lowest fares.

A nonstop flight from Fort Myers to Chicago Midway Airport takes 2h 54m, covering 1,106 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $283 to $2,619. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Fort Myers to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $151, which is 37% below the typical average for this route.

Chicago Midway Airport is 1 hour behind Fort Myers (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Fort Myers to Chicago Midway Airport range from $300 to $444, with an average of $357 over the past 12 months. Anything below $300 counts as a good deal.

JetBlue is the only airline on the Fort Myers to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.