Cheapest one-way flights from Orlando to Chicago in May from $44

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

One-Way flights

08 May Frontier Airlines direct
18 May Spirit Airlines
19 May Southwest Airlines direct
21 May Frontier Airlines direct
05 May Frontier Airlines
18 May Frontier Airlines direct
29 May Frontier Airlines direct
27 May Frontier Airlines
28 May Frontier Airlines direct
26 May Spirit Airlines

Also check the deals for return flights from Orlando to Chicago 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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