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

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

One-Way flights

11 Sep Frontier Airlines
16 Sep Southwest Airlines direct
20 Sep Southwest Airlines direct
20 Sep Frontier Airlines
23 Sep Southwest Airlines direct
30 Sep Southwest Airlines direct
11 Sep Southwest Airlines direct
27 Sep Southwest Airlines direct
27 Sep Frontier Airlines
10 Sep Southwest Airlines direct

Also check the deals for return flights from Boston to Chicago in September.

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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