AirHint found the following cheapest return flights from New York (JFK) to Chicago (ORD) in September 2025 (see full year).

Return flights

09 Sep - 16 Sep	jetBlue	direct
03 Sep - 10 Sep	American Airlines	direct
06 Sep - 10 Sep	American Airlines	direct
06 Sep - 13 Sep	Delta	direct
13 Sep - 20 Sep	Delta	direct
06 Sep - 23 Sep	Delta	direct
13 Sep - 16 Sep	Delta	direct
06 Sep - 09 Sep	Delta	direct
30 Sep - 01 Oct	Delta	direct
27 Sep - 04 Oct	Delta	direct
02 Sep - 04 Sep	jetBlue	direct
02 Sep - 05 Sep	jetBlue	direct
30 Sep - 02 Oct	Delta	direct
08 Sep - 01 Oct	jetBlue	direct
14 Sep - 06 Oct	Frontier Airlines
02 Sep - 02 Oct	Frontier Airlines
14 Sep - 06 Oct	Delta	direct

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

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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Cheapest return flights from New York to Chicago in September from 117€

Return flights