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

Return flights

25 Oct - 01 Nov	Austrian Airlines
25 Oct - 02 Nov	Austrian Airlines
28 Oct - 05 Nov	Austrian Airlines
24 Oct - 01 Nov	Austrian Airlines
29 Oct - 03 Nov	Lufthansa
24 Oct - 02 Nov	Austrian Airlines
18 Oct - 08 Nov	Austrian Airlines
18 Oct - 14 Nov	Air Canada
17 Oct - 23 Nov	LOT
24 Oct - 31 Oct	Austrian Airlines
19 Oct - 26 Oct	SWISS
18 Oct - 25 Oct	Austrian Airlines
24 Oct - 30 Nov	Lufthansa
07 Oct - 19 Oct	LOT
04 Oct - 31 Oct	Austrian Airlines
07 Oct - 28 Oct	Air Canada
14 Oct - 24 Oct	Austrian Airlines
10 Oct - 24 Oct	LOT
08 Oct - 18 Oct	Lufthansa
08 Oct - 19 Oct	Lufthansa

Also check the deals for one-way flights from Chicago to Skopje 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 Skopje in October from $484

Return flights