Cheapest one-way flights from New York to Chicago in May from 28€

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

One-Way flights

03 May Frontier Airlines direct
02 May Frontier Airlines direct
24 May Frontier Airlines
05 May Frontier Airlines
06 May Frontier Airlines
19 May Southwest Airlines direct
06 May Southwest Airlines direct
05 May Southwest Airlines direct
26 May Southwest Airlines direct
20 May Southwest Airlines direct

Also check the deals for return flights from New York 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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