Cheap flights from Chicago to Fort Myers

One-way fares from $184 · CHI → FMY · prices found by travellers in the last 48 hours

Compare all dates Fort Myers → Chicago
Cheapest fare
$184

American Airlines · Fri, Nov 6

Cheapest month
November

from $184

Direct flights
Yes

American Airlines, United Airlines and Southwest Airlines

Flight time
2h 45m

1,770 km

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Cheapest month to fly from Chicago to Fort Myers

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

  1. November 2026 Cheapest $184

Cheapest dates in November 2026

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

American Airlines
Depart14:50 Fri, Nov 6ORD → RSW 3h 00m · Direct
$184one way, per person
View deal
American Airlines
Depart14:50 Tue, Nov 10ORD → RSW 3h 00m · Direct
$189one way, per person
View deal
Allegiant Air
Depart09:30 Thu, Nov 12RFD → RSW 7h 30m · 2 stops
$195one way, per person
View deal
American Airlines
Depart14:50 Mon, Nov 9ORD → RSW 3h 00m · Direct
$199one way, per person
View deal
United Airlines
Depart10:43 Sat, Nov 7ORD → RSW 3h 06m · Direct
$211one way, per person
View deal
jetBlue
Depart13:00 Wed, Nov 4ORD → RSW 6h 28m · 1 stop
$220one way, per person
View deal
Southwest Airlines
Depart05:05 Thu, Nov 5MDW → RSW 2h 45m · Direct
$227one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Fort Myers

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in Fort MyersCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in Fort MyersTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in Fort MyersPre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in Fort MyersCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Fort Myers

Chicago (CHI) and Fort Myers (FMY) are about 1,770 km apart. Direct flights take around 2h 45m, and recent direct fares were with American Airlines, United Airlines and Southwest Airlines. Over the next few months, one-way fares start from $184, and November 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 Chicago to Fort Myers?

The cheapest one-way fare we've seen recently is $184 with American Airlines, departing Friday, November 6, 2026.

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

November 2026 currently has the lowest fares, from $184 one way.

Are there direct flights from Chicago to Fort Myers?

Yes. Recent direct fares were with American Airlines, United Airlines and Southwest Airlines.

How long is the flight from Chicago to Fort Myers?

A direct flight takes about 2h 45m. Chicago and Fort Myers are around 1,770 km apart.

Which airlines fly from Chicago to Fort Myers?

Recent fares on this route were with American Airlines, Allegiant Air, United Airlines, jetBlue and Southwest Airlines.

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