Cheapest return flights from New York to Chicago in October from 186€

Best time to book flights for New York (LGA) to Chicago (ORD) flights at AirHint

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

Return flights

08 Oct - 10 Oct Delta direct
01 Oct - 06 Oct Delta direct
02 Oct - 09 Oct United direct
08 Oct - 08 Oct United direct
10 Oct - 14 Oct Delta direct
15 Oct - 19 Oct United direct
16 Oct - 21 Oct United direct
06 Oct - 24 Oct United direct
22 Oct - 24 Oct United direct

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.

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