Cheapest return flights from New York to Chicago in May from $188

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

Return flights

01 May - 04 May American Airlines direct
23 May - 30 May American Airlines direct
06 May - 08 May United direct
04 May - 05 May American Airlines direct
26 May - 30 May United direct
13 May - 14 May Delta direct
01 May - 03 May United direct
07 May - 10 May United direct
03 May - 06 May Delta direct
09 May - 16 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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