Cheapest return flights from New York to Chicago in May from 76€

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

Return flights

02 May - 04 May Frontier Airlines direct
02 May - 03 May Frontier Airlines direct
04 May - 04 May Frontier Airlines
03 May - 05 May Frontier Airlines
02 May - 02 May Frontier Airlines
13 May - 19 May Southwest Airlines direct
05 May - 05 May Southwest Airlines direct
12 May - 12 May Southwest Airlines direct
24 May - 27 May Frontier Airlines
20 May - 27 May Southwest Airlines direct
06 May - 03 Jun Southwest Airlines direct
27 May - 03 Jun Southwest Airlines direct
30 May - 02 Jun Southwest Airlines direct
28 May - 02 Jun Southwest Airlines direct
26 May - 06 Jun Southwest Airlines direct
28 May - 01 Jun Southwest Airlines direct
29 May - 03 Jun Southwest Airlines direct
29 May - 02 Jun Southwest Airlines direct
29 May - 01 Jun Southwest Airlines direct
14 May - 04 Jun Frontier Airlines

Also check the deals for one-way flights from New York to Chicago in May.

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