AirHint found the following cheapest one-way flights from Orlando (MCO) to Chicago (MDW) in October 2026 (see full year).
One-Way flights
| 06 Oct | Southwest Airlines | direct | |
| 17 Oct | Southwest Airlines | ||
| 12 Oct | Southwest Airlines | ||
| 09 Oct | Southwest Airlines | direct | |
| 12 Oct | Southwest Airlines | direct | |
| 17 Oct | Southwest Airlines | direct |
Also check the deals for return flights from Orlando to Chicago in October.
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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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