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Flights from Fort Myers to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

RSW to MDW flights and routes map RSW to MDW – All flight route options from Southwest Florida International Airport, Florida, USA to Chicago Midway International, Illinois, USA. These flights are operated by 2 airlines. Fly non-stop with Southwest Airlines or choose from 11 different transit flights. The shortest flight time is 2 hours and 55 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA RSW Southwest Florida Airport Fort Myers, FL, USA
USA MDW Chicago Midway , IL, USA
RSW
Southwest Florida Airport
USAFort Myers, FL, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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12 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 2-3 flights per day.

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2h 55m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 55m
2-3 flights per day.
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1 stop route options with the same airline:

Duration

Via Saint Louis STL
1 stop with Southwest Airlines. 1-2 flights per day.

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4h 58m

Via Saint Louis STL
1 stop with Southwest Airlines.
4h 58m
1-2 flights per day.
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Via Atlanta ATL
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 25m

Via Atlanta ATL
1 stop with Southwest Airlines.
5h 25m
0-1 flights per day.
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Via Buffalo BUF
1 stop with Southwest Airlines.

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5h 30m

Via Buffalo BUF
1 stop with Southwest Airlines.
5h 30m
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Via Pittsburgh PIT
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 30m

Via Pittsburgh PIT
1 stop with Southwest Airlines.
5h 30m
0-1 flights per day.
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Via Columbus CMH
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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5h 33m

Only saturdays
Via Columbus CMH
1 stop with Southwest Airlines.
5h 33m
0-1 flights per day.
Only saturdays
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Via Detroit DTW
1 stop with Delta Air Lines. 0-2 flights per day.

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5h 46m

Via Detroit DTW
1 stop with Delta Air Lines.
5h 46m
0-2 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 4-8 flights per day.

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5h 54m

Via Atlanta ATL
1 stop with Delta Air Lines.
5h 54m
4-8 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 1-2 flights per day.

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5h 55m

Via Nashville BNA
1 stop with Southwest Airlines.
5h 55m
1-2 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.

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6h 00m

Via Kansas City MCI
1 stop with Southwest Airlines.
6h 00m
0-1 flights per day.
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Via Cleveland CLE
1 stop with Southwest Airlines. 0-1 flights per day.

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6h 35m

Via Cleveland CLE
1 stop with Southwest Airlines.
6h 35m
0-1 flights per day.
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Via Baltimore BWI
1 stop with Southwest Airlines. 2-3 flights per day.

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7h 20m

Via Baltimore BWI
1 stop with Southwest Airlines.
7h 20m
2-3 flights per day.
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Via Raleigh/Durham RDU
1 stop with Southwest Airlines. 0-1 flights per day.

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8h 35m

Via Raleigh/Durham RDU
1 stop with Southwest Airlines.
8h 35m
0-1 flights per day.
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Fort Myers to Chicago flights

There are over 12 airlines and as many as 90 flights every week to this destination. You can fly non-stop to Chicago (MDW) from Fort Myers (RSW) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Saint Louis, Buffalo or any other of the 11 alternatives with connectiing airports.

Fort Myers to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 5:00 am to 9:00 pm. You can also catch a transit flight via Saint Louis or Atlanta.

With Delta Air Lines

If you choose to fly with Delta Air Lines from Fort Myers to Chicago you can make a transit either via Detroit or via Atlanta. The route via Detroit is 8 minutes faster. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Southwest Florida International Airport to Midway International Airport

The shortest flight time between RSW and MDW is 3 hours.

ViaTotal flight timeLayover timeDistance
Direct3h 0m-1113 miles (1791 km)
STL Saint Louis4h 58m45m1238 miles (1992 km)
BUF Buffalo5h 30m1h 5m1621 miles (2608 km)
PIT Pittsburgh5h 30m45m1376 miles (2214 km)
CMH Columbus5h 33m2h 15m1221 miles (1965 km)
DTW Detroit5h 46m1h 56m1322 miles (2127 km)
ATL Atlanta5h 54m2h 8m1113 miles (1791 km)
BNA Nashville5h 55m50m1124 miles (1809 km)
MCI Kansas City6h 0m1h 15m1569 miles (2525 km)
CLE Cleveland6h 35m2h 30m1340 miles (2156 km)
BWI Baltimore7h 20m50m1538 miles (2475 km)
RDU Raleigh/Durham8h 35m2h 10m1307 miles (2103 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.RSW-MDW flight routesFort Myers to Chicago flight routes illustrated on a map.
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Fort Myers - Chicago route map and flight paths
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You can fly non-stop from Fort Myers (RSW) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 3 hours. If you travel with a connecting flight instead, for example via Saint Louis, the total flight time will be 4 hours and 58 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Southwest Airlines and Delta Air Lines is also an option.

The flight time between Southwest Florida Airport (RSW) and Chicago Midway International (MDW) is approximately 3 hours. The distance between the two airports is 1113 miles (or 1791 kilometers).

Yes, you can fly non-stop to MDW from RSW with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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