AirHint found the following cheapest one-way flights from Chicago (MDW) to Tokyo (NRT) in October 2025 (see full year).

One-Way flights

30 Oct	Frontier Airlines
24 Oct	Frontier Airlines
12 Oct	Frontier Airlines
27 Oct	Frontier Airlines
13 Oct	Frontier Airlines
03 Oct	Frontier Airlines
14 Oct	Porter Airlines (Canada) Ltd
21 Oct	Delta
18 Oct	Volaris

Also check the deals for return flights from Chicago to Tokyo 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 one-way flights from Chicago to Tokyo in October from $454

One-Way flights