Cheapest return flights from Orlando to Chicago in May from $69

AirHint found the following cheapest return flights from Orlando (ORL) to Chicago (MDW) in May 2026 (see full year).

Return flights

09 May - 16 May Frontier Airlines direct
14 May - 17 May Frontier Airlines direct
01 May - 08 May Frontier Airlines direct
01 May - 04 May Frontier Airlines direct
15 May - 17 May Frontier Airlines direct
16 May - 17 May Frontier Airlines direct
15 May - 18 May Frontier Airlines direct
03 May - 16 May Frontier Airlines direct
03 May - 07 May Frontier Airlines
06 May - 07 May Frontier Airlines
30 May - 02 Jun Delta

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

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