Flights Fort Myers → Chicago
RSW → MDW
How long is the flight from Fort Myers to Chicago?
The flight from Fort Myers (RSW) to Chicago (MDW) takes about 2h 39m. This is an estimate based on the distance between the two airports: the real time depends on the aircraft, wind and any stops.
Route overview
The flight route from Fort Myers to Chicago operates with a Boeing 717 and has an on-time performance rate of 67%, with average delays of 20.6 minutes per flight. Over the course of a year, this route sees approximately 377 flights serving one of the busiest airports in terms of passenger traffic, handling nearly 19.9 million passengers annually.
Your rights on this US flight (DOT)
US flights have no statutory cash compensation for delays. Under the US DOT rules, if your flight is cancelled or significantly changed and you decline rebooking, you're owed an automatic refund of the unused ticket. The tarmac-delay limit is 3 hours (domestic) / 4 hours (international). Amenities for controllable delays depend on each airline's contract of carriage.
US flight refund rules & checker →General information, not legal advice.
The Fort Myers (RSW) → Chicago (MDW) route is operated by Southwest Airlines. Across 749 flights monitored in recent months, 67% arrived on time (within 15 min of schedule), with an average delay of 20 minutes. The cancellation rate is 2.27%. FlightGuard's average computed risk is 26/100 (medium), updated in real time from weather, ATC delays, strikes, NOTAMs, fuel and flight history. At Chicago the average ATFM delay is 5.5 minutes (main cause: atfm). Departing from Fort Myers the average ATFM delay is 5.5 minutes.
Heading to Chicago: what to expect in this direction
Flying from Fort Myers (RSW) to Chicago (MDW) heads north for about 1,782 km, a flight time of roughly 2h 39m.
Departures from Fort Myers on this leg cluster in the morning window: about 36% of RSW-MDW flights take off then.
Air-traffic congestion: departing Fort Myers the average ATFM delay is 5.5 min (atfm); arriving into Chicago it is 5.5 min (atfm).
Across 749 tracked RSW-MDW flights, 67% left on time with an average delay of 20 min and a 2.3% cancellation rate.
Route facts
Flights on this route
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Airline punctuality on this route
| Airline | On-time | Average delay | Cancellations |
|---|---|---|---|
| Southwest Airlines (WN) | 75% | 5 min | 0.3% |
Airlines operating RSW-MDW
Airports
Frequently asked questions about RSW-MDW
The flight from Fort Myers (RSW) to Chicago (MDW) takes about 2h 39m. This is an estimate based on the distance between the two airports: the real time depends on the aircraft, wind and any stops.
On the Fort Myers (RSW) -> Chicago (MDW) route, on-time performance is 67% with an average delay of 20 minutes, based on 749 tracked flights.
The cancellation rate on Fort Myers-Chicago is 2.27% across 749 monitored flights.
The route is operated by 1 airline: Southwest Airlines.
Enter your flight number on FlightGuard for a real-time analysis based on 9 factors: weather at Chicago, ATC delays, strikes, NOTAMs, fuel, airline punctuality and recent trends.
US flights have no statutory cash compensation for delays. Under US DOT rules, if the airline cancels or significantly changes your flight and you decline rebooking, you're owed an automatic refund of the unused ticket. The tarmac-delay limit is 3 hours (domestic) / 4 hours (international). Meals or hotels for controllable delays depend on each airline's contract of carriage.
