Cheapest return flights from Fort Myers to Chicago in May from $218

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

Return flights

08 May - 11 May jetBlue
15 May - 18 May jetBlue
29 May - 01 Jun jetBlue
01 May - 04 May United direct
08 May - 11 May American Airlines direct
15 May - 18 May American Airlines direct
22 May - 25 May United direct
29 May - 01 Jun American Airlines direct

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

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