Cheapest return flights from Chicago to Orlando in May from $65

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

Return flights

16 May - 17 May Frontier Airlines direct
04 May - 07 May Frontier Airlines direct
10 May - 15 May Frontier Airlines direct
14 May - 17 May Frontier Airlines direct
03 May - 08 May Frontier Airlines direct
11 May - 17 May Frontier Airlines direct
15 May - 17 May Frontier Airlines direct
10 May - 17 May Frontier Airlines direct
15 May - 18 May Frontier Airlines direct
05 May - 09 May Frontier Airlines
11 May - 01 Jun Frontier Airlines direct
20 May - 08 Jun Frontier Airlines
15 May - 05 Jun Frontier Airlines
15 May - 05 Jun Frontier Airlines direct
17 May - 03 Jun Frontier Airlines
12 May - 02 Jun Frontier Airlines
13 May - 03 Jun Frontier Airlines
26 May - 01 Jun Frontier Airlines
29 May - 02 Jun Southwest Airlines direct
28 May - 01 Jun Southwest Airlines direct

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

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