There are most likely no direct flights on the Fort Myers — Chicago route
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A non-stop flight is the most convenient and comfortable way to fly from Fort Myers to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
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There are most likely no direct flights on the Fort Myers — Chicago route
Fort Myers — Chicago
12/04/2026
Departure
Direct flight
F92033
starting at $93
Fort Myers — Chicago
12/03/2026
Departure
Direct flight
F92033
starting at $97
Fort Myers — Chicago
12/19/2026
Departure
Direct flight
F92033
starting at $105
Fort Myers — Chicago
12/05/2026
Departure
Direct flight
WN2106
starting at $161
Fort Myers — Chicago
11/12/2026
Departure
Direct flight
AA669
starting at $181
Fort Myers — Chicago
01/04/2027
Departure
Direct flight
UA2066
starting at $330
Fort Myers — Chicago
01/05/2027
Departure
Direct flight
UA2420
starting at $348
Fort Myers — Chicago
01/03/2027
Departure
Direct flight
F92033
starting at $444
Fort Myers — Chicago
01/02/2027
Departure
Direct flight
UA2440
starting at $487
Fort Myers — Chicago
11/13/2026
Departure
Direct flight
AA1238
starting at $176
starting at $93
starting at $161
starting at $176
starting at $190
The route Fort Myers — Chicago is served by many carriers — 4 in total, including Frontier Airlines, Southwest Airlines, American Airlines, and United Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $93) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
The cheapest one-way flight from Fort Myers to Chicago departs on 12/04/2026, is operated by Frontier Airlines and costs $93
The cheapest roundtrip flight from Fort Myers to Chicago departs on 12/17/2026, is operated by Frontier Airlines and costs $285
Fastest flight from Fort Myers to Chicago takes 2h 55m
There are direct flights on this route 6 days a week: Su, Mo, Tu, Th, Fr, and Sa
The distance between Fort Myers and Chicago is 1773km (1099 miles). There are 24 direct flights from Fort Myers to Chicago. The time difference between Fort Myers and Chicago is 1h. Flights from Fort Myers begin at 6:35 AM. The latest flight from Fort Myers departs at 6:40 PM
In different months, ticket prices from Fort Myers to Chicago vary: minimum — $106 (December 2026), maximum — $421 (January 2027). Typically, the flight costs $263–$421.
The cheapest flight ticket from Fort Myers to Chicago according to data for the last 48 hours costs $93
Often the best time to buy tickets from Fort Myers to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Fort Myers to Chicago can be found flying in these months: December, January.
The fastest flights from Fort Myers to Chicago start from 2 hours 55 minutes in the air.
The following airlines operate direct flights on the route Fort Myers — Chicago: Frontier Airlines, Southwest Airlines, American Airlines
We couldn't find any special offers for flights from Fort Myers to Chicago