Cheapest one-way flights from Chicago to Orlando in May from $27

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

One-Way flights

02 May Frontier Airlines direct
15 May Frontier Airlines direct
04 May Frontier Airlines direct
03 May Frontier Airlines direct
16 May Frontier Airlines direct
06 May Frontier Airlines
20 May Frontier Airlines
19 May Frontier Airlines
14 May Frontier Airlines
01 May Frontier Airlines

Also check the deals for return flights from Chicago to Orlando in May.

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The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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