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
$ 157
direct
11 Sep
- 15 Sep
Southwest Airlines
$ 157
direct
12 Sep
- 15 Sep
Southwest Airlines
$ 157
direct
26 Sep
- 28 Sep
Southwest Airlines
$ 157
direct
25 Sep
- 28 Sep
Southwest Airlines
$ 157
direct
06 Sep
- 08 Sep
Southwest Airlines
$ 157
direct
11 Sep
- 16 Sep
Southwest Airlines
$ 157
direct
10 Sep
- 15 Sep
Southwest Airlines
$ 157
direct
26 Sep
- 29 Sep
Southwest Airlines
$ 157
direct
10 Sep
- 14 Sep
Southwest Airlines
$ 187
direct
30 Sep
- 08 Oct
Southwest Airlines
$ 233
Also check the deals for one-way flights from Boston to Chicago in September .
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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