Cheapest one-way flights from Chicago to Orlando in May from $22

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

One-Way flights

16 May Frontier Airlines direct
02 May Frontier Airlines direct
01 May Frontier Airlines direct
17 May Frontier Airlines direct
18 May Frontier Airlines direct
10 May Frontier Airlines direct
09 May Frontier Airlines
19 May Frontier Airlines
20 May Frontier Airlines
13 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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