Cheapest return flights from Chicago to Orlando in October from $422

AirHint found the following cheapest return flights from Chicago (MDW) to Orlando (MCO) in October 2026 (see full year).

Return flights

13 Oct - 27 Oct Southwest Airlines
25 Oct - 31 Oct Southwest Airlines
10 Oct - 14 Oct Delta
11 Oct - 14 Oct Delta
30 Oct - 02 Nov Delta

Also check the deals for one-way flights from Chicago to Orlando 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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