Cheapest return flights from Chicago to Fort Myers in May from $268

AirHint found the following cheapest return flights from Chicago (ORD) to Fort Myers (RSW) in May 2026 (see full year).

Return flights

04 May - 14 May jetBlue
12 May - 12 May United direct
12 May - 19 May United direct
04 May - 14 May United direct
23 May - 26 May United
14 May - 20 May American Airlines direct
15 May - 17 May jetBlue
08 May - 11 May United direct
21 May - 25 May jetBlue
29 May - 29 May United direct

Also check the deals for one-way flights from Chicago to Fort Myers in May.

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The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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