Cheapest return flights from New York to Chicago in May from $180

AirHint found the following cheapest return flights from New York (JFK) to Chicago (ORD) in May 2026 (see full year).

Return flights

06 May - 09 May jetBlue direct
01 May - 03 May jetBlue direct
20 May - 23 May jetBlue direct
24 May - 31 May jetBlue direct
15 May - 18 May jetBlue direct
14 May - 17 May jetBlue direct
28 May - 01 Jun jetBlue direct
08 May - 10 May jetBlue direct
01 May - 01 May Delta direct

Also check the deals for one-way 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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