Cheapest return flights from Boston to Chicago in September from $157

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

Return flights

20 Sep - 23 Sep Southwest Airlines direct
11 Sep - 15 Sep Southwest Airlines direct
12 Sep - 15 Sep Southwest Airlines direct
26 Sep - 28 Sep Southwest Airlines direct
25 Sep - 28 Sep Southwest Airlines direct
06 Sep - 08 Sep Southwest Airlines direct
11 Sep - 16 Sep Southwest Airlines direct
10 Sep - 15 Sep Southwest Airlines direct
26 Sep - 29 Sep Southwest Airlines direct
10 Sep - 14 Sep Southwest Airlines direct
30 Sep - 08 Oct Southwest Airlines

Also check the deals for one-way 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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