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

Return flights

27 Oct - 03 Nov	Korean Air
28 Oct - 04 Nov	Korean Air
27 Oct - 09 Nov	Korean Air
01 Oct - 05 Oct	Cathay Pacific
02 Oct - 05 Oct	Cathay Pacific
02 Oct - 06 Oct	Cathay Pacific
19 Oct - 03 Nov	Cathay Pacific
17 Oct - 20 Oct	Delta
06 Oct - 08 Oct	Frontier Airlines
02 Oct - 04 Oct	United
13 Oct - 25 Oct	China Airlines

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

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 Chicago to Singapore in October from $723

Return flights