Cheap flights from Fort Myers to Chicago

One-way fares from $94 · FMY → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Fort Myers
Cheapest fare
$94

Frontier Airlines · Fri, Dec 4

Cheapest month
December

from $94

Direct flights
Yes

Frontier Airlines and Southwest Airlines

Flight time
2h 55m

1,770 km

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Cheapest month to fly from Fort Myers to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 $167
  2. December 2026 Cheapest $94
  3. January 2027 $194

Cheapest dates in December 2026

The lowest fares we've seen for each day, cheapest first.

Frontier Airlines
Depart20:31 Fri, Dec 4RSW → ORD 3h 18m · Direct
$94one way, per person
View deal
Frontier Airlines
Depart20:31 Thu, Dec 3RSW → ORD 3h 18m · Direct
$98one way, per person
View deal
Frontier Airlines
Depart21:57 Sat, Dec 19RSW → ORD 3h 21m · Direct
$106one way, per person
View deal
Southwest Airlines
Depart06:50 Sat, Dec 5RSW → MDW 2h 55m · Direct
$162one way, per person
View deal
See every date in December 2026 →

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About flights from Fort Myers to Chicago

Fort Myers (FMY) and Chicago (CHI) are about 1,770 km apart. Direct flights take around 2h 55m, and recent direct fares were with Frontier Airlines and Southwest Airlines. Over the next few months, one-way fares start from $94, and December 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Fort Myers to Chicago?

The cheapest one-way fare we've seen recently is $94 with Frontier Airlines, departing Friday, December 4, 2026. Over the coming months, the lowest fare in each month ranges from $94 to $194.

What is the cheapest month to fly from Fort Myers to Chicago?

December 2026 currently has the lowest fares, from $94 one way.

Are there direct flights from Fort Myers to Chicago?

Yes. Recent direct fares were with Frontier Airlines and Southwest Airlines.

How long is the flight from Fort Myers to Chicago?

A direct flight takes about 2h 55m. Fort Myers and Chicago are around 1,770 km apart.

Which airlines fly from Fort Myers to Chicago?

Recent fares on this route were with Frontier Airlines, United Airlines and Southwest Airlines.

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