Cheapest return flights from Chicago to Orlando in May from $417

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

Return flights

20 May - 26 May Southwest Airlines direct
26 May - 28 May Southwest Airlines direct
08 May - 11 May Southwest Airlines direct
07 May - 11 May Southwest Airlines direct
12 May - 17 May Delta
30 May - 06 Jun Delta
12 May - 17 May Southwest Airlines direct
30 May - 06 Jun Southwest Airlines direct

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

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