Cheapest return flights from Chicago to Orlando in September from $416

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

Return flights

21 Sep - 24 Sep Southwest Airlines direct
10 Sep - 13 Sep Southwest Airlines direct
09 Sep - 23 Sep Southwest Airlines direct
02 Sep - 07 Sep Southwest Airlines direct
04 Sep - 09 Sep Delta
04 Sep - 09 Sep Southwest Airlines direct
16 Sep - 21 Sep Delta
27 Sep - 04 Oct Delta

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

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