Cheapest return flights from New York to Chicago in October from 41€

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

Return flights

07 Oct - 08 Oct Spirit Airlines direct
07 Oct - 18 Oct Spirit Airlines direct
01 Oct - 08 Oct Spirit Airlines
01 Oct - 07 Oct Spirit Airlines
01 Oct - 18 Oct Spirit Airlines
04 Oct - 08 Oct Spirit Airlines
04 Oct - 07 Oct Spirit Airlines
04 Oct - 18 Oct Spirit Airlines
08 Oct - 18 Oct Spirit Airlines
15 Oct - 18 Oct Spirit Airlines
28 Oct - 04 Nov Frontier Airlines direct
29 Oct - 04 Nov Frontier Airlines direct
30 Oct - 04 Nov Frontier Airlines direct
30 Oct - 03 Nov Frontier Airlines direct
30 Oct - 02 Nov Frontier Airlines direct
29 Oct - 07 Nov Frontier Airlines direct
29 Oct - 05 Nov Frontier Airlines direct
15 Oct - 01 Nov Spirit Airlines
15 Oct - 05 Nov Spirit Airlines
15 Oct - 04 Nov Spirit Airlines

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

Skyscanner

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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.