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

Chicago Midway International Airport (MDW) is ADA-compliant. Travelers with reduced mobility flying through the airport can access several services and amenities, including wheelchair assistance, dedicated lanes, elevators, accessible restrooms, and accessible parking spaces. For wheelchair help, contact your airline at least 48 hours before your trip or when making a reservation.

Public bus Route 50, run by LeeTran, provides connections to Daniels Parkway and U.S. 41, where you can connect to other routes. The journey time is around 1h 4 min, including a layover time of around 17 minutes. Different rental companies are available onsite in the Ground Transportation area. You can also opt for a taxi or hotel shuttle.

For sustainable flights from Chicago Midway Airport to Fort Myers, you can book Southwest Airlines, which has a direct flight with reduced carbon emissions. It emits 6% less CO₂ than a typical flight on this route. The airline has adopted several sustainable practices in its operations to lower greenhouse gas emissions.

If you have a minor flying alone, consider booking Southwest Airlines, which offers an unaccompanied minor service on its direct flights at a fee. This service is mandatory for children aged 5 to 11. Your child will be escorted to the flight by a Southwest Airlines employee, receive the necessary assistance onboard, and be escorted to the person picking them up upon arrival.

Among airlines operating Chicago Midway Airport to Fort Myers flights:

• Southwest: offers free seat selection

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

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

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

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

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 Chicago Midway Airport to Fort Myers.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $332 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $395 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$91 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Airbus A321neo family is used most often on this route, operated mainly by United Airlines and Spirit Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

One-stop flights from Chicago Midway Airport to Fort Myers most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 79% of one-stop connections
• Nashville Intl (BNA) - 3% of one-stop connections
• Columbus (CMH) - 3% of one-stop connections
• Dallas Love Field (DAL) - 3% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

On the Chicago Midway Airport to Fort Myers route, being flexible with your departure day can save you up to 31%. Saturday is the cheapest day at $346 round-trip on average, while Sunday is the most expensive at $497: a $151 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Morning is the busiest departure period on Chicago Midway Airport to Fort Myers 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 Fort Myers are Lee Memorial Hospital, Terry Park Ballfield and Edison Mall. These are among the most viewed places in Fort Myers on KAYAK.

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

• Earliest: departs at 5:05 am and lands at 7:51 am
• Latest: departs at 8:55 pm and lands at 11:41 pm.

The flight takes about 2h 46m.

Last-minute fares on this route - booked within 2 weeks of departure - run 24% above the route average of $387. Book 18 weeks before departure for the lowest fares.

A nonstop flight from Chicago Midway Airport to Fort Myers takes 2h 46m, 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 $277 to $2,438. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Chicago Midway Airport to Fort Myers are currently lower than usual. Average one-way flight prices are about $155, which is 31% below the typical average for this route.

Flying via Nashville Intl (BNA) gives the shortest average 1-stop total travel time at 4h 29m, compared with 4h 39m via Columbus (CMH) and 4h 49m via Lambert-St Louis (STL).

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

Fort Myers SW Florida Intl Airport (RSW) hosts 5 major car rental companies, with daily rates starting from around $20 for economy cars. Top options include:
• Hertz
• Dollar
• Thrifty
• Fox
• Budget

Round-trip flights from Chicago Midway Airport to Fort Myers range from $308 to $499, with an average of $387 over the past 12 months. Anything below $308 counts as a good deal.