Fort Myers to Chicago: what the flight costs
In the last 60 days we checked this route 6 times. The typical round trip was $592 per person and the lowest $494, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | $494 |
| Typical (median) | $592 |
| Price checks, 60 days | 6 |
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Trips we picked on this route
$592 $494 per person, round trip, taxes and fees included You save $98 (17%)
the typical fare on this route
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| Oct 12, 2026 | Oct 23–25, 2026 | $600 | F9 | with a stop | 38h 7m | Kiwi.com |
| Oct 12, 2026 | Oct 23–25, 2026 | $494 | Frontier | with a stop | 10h 54m | Google Flights |
| Oct 12, 2026 | Oct 16–18, 2026 | $735 | UA | with a stop | 9h 45m | Kiwi.com |
| Oct 12, 2026 | Oct 16–18, 2026 | $494 | Frontier | with a stop | 10h 54m | Google Flights |
| Oct 12, 2026 | Oct 23–25, 2026 | $709 | UA | with a stop | 8h 55m | Kiwi.com |
| Oct 12, 2026 | Oct 16–18, 2026 | $584 | F9 | with a stop | 10h 54m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Fort Myers to Chicago
What does a round trip from Fort Myers to Chicago usually cost?
Over the last 60 days the typical price we found was $592 per person, taxes and fees included, across 6 checks; the lowest was $494.
When is the best time to fly from Fort Myers to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Fort Myers to Chicago?
No, a government photo ID is enough for US citizens.