Cheapest one-way flights from Boston to Chicago in October from $72

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

One-Way flights

30 Oct Frontier Airlines
01 Oct Southwest Airlines direct
30 Oct Southwest Airlines direct
31 Oct Frontier Airlines
07 Oct Southwest Airlines direct
16 Oct Southwest Airlines direct
16 Oct Frontier Airlines
02 Oct Southwest Airlines direct
29 Oct Southwest Airlines direct
03 Oct Southwest Airlines direct

Also check the deals for return flights from Boston 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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