Cheapest one-way flights from Orlando to Chicago in May from $51

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

One-Way flights

16 May Spirit Airlines direct
09 May Spirit Airlines direct
12 May Spirit Airlines direct
23 May Spirit Airlines direct
27 May Spirit Airlines direct
28 May Spirit Airlines direct
30 May Spirit Airlines direct
15 May Frontier Airlines direct
07 May Frontier Airlines direct
04 May Spirit Airlines direct

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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