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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 3 airlines. Fly non-stop with Southwest Airlines or choose from 10 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 Indianapolis IND
1 stop with Southwest Airlines.
Begins in 5/8

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4h 25m

Begins in 5/8
Via Indianapolis IND
1 stop with Southwest Airlines.
4h 25m
Begins in 5/8
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Via Columbus CMH
1 stop with Southwest Airlines. 0-1 flights per day.

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4h 40m

Via Columbus CMH
1 stop with Southwest Airlines.
4h 40m
0-1 flights per day.
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Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.
Thu & Sun

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5h 02m

Thu & Sun
Via Atlanta ATL
1 stop with Frontier Airlines.
5h 02m
0-1 flights per day.
Thu & Sun
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Via Saint Louis STL
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 05m

Via Saint Louis STL
1 stop with Southwest Airlines.
5h 05m
0-1 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 5-6 flights per day.

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5h 16m

Via Atlanta ATL
1 stop with Delta Air Lines.
5h 16m
5-6 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 0-2 flights per day.
Fri,Sat & Sun

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5h 20m

Fri,Sat & Sun
Via Nashville BNA
1 stop with Southwest Airlines.
5h 20m
0-2 flights per day.
Fri,Sat & Sun
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Via Detroit DTW
1 stop with Delta Air Lines. 0-1 flights per day.
Only saturdays

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5h 27m

Only saturdays
Via Detroit DTW
1 stop with Delta Air Lines.
5h 27m
0-1 flights per day.
Only saturdays
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Via Pittsburgh PIT
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 38m

Via Pittsburgh PIT
1 stop with Southwest Airlines.
5h 38m
0-1 flights per day.
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Via Orlando MCO
1 stop with Southwest Airlines.
Begins in 5/8

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6h 00m

Begins in 5/8
Via Orlando MCO
1 stop with Southwest Airlines.
6h 00m
Begins in 5/8
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Via Kansas City MCI
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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6h 55m

Only sundays
Via Kansas City MCI
1 stop with Southwest Airlines.
6h 55m
0-1 flights per day.
Only sundays
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Via Baltimore BWI
1 stop with Southwest Airlines. 1-4 flights per day.

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7h 15m

Via Baltimore BWI
1 stop with Southwest Airlines.
7h 15m
1-4 flights per day.
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Via Detroit DTW
1 stop with Southwest Airlines.
Begins in 8/11

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7h 30m

Begins in 8/11
Via Detroit DTW
1 stop with Southwest Airlines.
7h 30m
Begins in 8/11
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Fort Myers to Chicago flights

There are over 11 airlines and as many as 103 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 Indianapolis, Columbus or any other of the 10 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 Indianapolis or Columbus.

With Frontier Airlines

If you fly from Fort Myers with Frontier Airlines you will do a stopover in Atlanta, ATL before reaching Chicago. This flight trip will take 5 hours and 2 minutes and you can fly every Thursday or Sunday with departures at 19 in the evening.

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

The shortest flight time between RSW and MDW is 2 hours and 55 minutes.

ViaTotal flight timeLayover timeDistance
Direct2h 55m-1113 miles (1791 km)
IND Indianapolis4h 25m2h 10m1115 miles (1794 km)
CMH Columbus4h 40m2h 25m1221 miles (1965 km)
STL Saint Louis5h 5m2h 50m1238 miles (1992 km)
ATL Atlanta5h 16m2h 22m1113 miles (1791 km)
BNA Nashville5h 20m55m1124 miles (1809 km)
DTW Detroit5h 27m1h 15m1322 miles (2127 km)
PIT Pittsburgh5h 38m1h 5m1376 miles (2214 km)
MCO Orlando6h 0m1h 25m1130 miles (1818 km)
MCI Kansas City6h 55m2h 35m1569 miles (2525 km)
BWI Baltimore7h 15m55m1538 miles (2475 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 2 hours and 55 minutes. If you travel with a connecting flight instead, for example via Indianapolis, the total flight time will be 4 hours and 25 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 2 hours and 55 minutes. 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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