Cheapest return flights from New York to Chicago in October from 235€

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

Return flights

01 Oct - 07 Oct Southwest Airlines direct
20 Oct - 25 Oct Southwest Airlines direct
10 Oct - 11 Oct Southwest Airlines
08 Oct - 11 Oct Southwest Airlines
09 Oct - 13 Oct Southwest Airlines
08 Oct - 12 Oct Southwest Airlines
09 Oct - 11 Oct Southwest Airlines
09 Oct - 12 Oct Southwest Airlines
26 Oct - 01 Nov Delta

Also check the deals for one-way flights from New York 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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