Cheapest return flights from Boston to Chicago in October from $144
AirHint found the following cheapest return flights from Boston (BOS) to Chicago (MDW)
in October 2025 (see full year ).
Return flights
16 Oct
- 18 Oct
Frontier Airlines
$ 144
23 Oct
- 26 Oct
Frontier Airlines
$ 144
16 Oct
- 19 Oct
Frontier Airlines
$ 155
15 Oct
- 21 Oct
Southwest Airlines
$ 157
direct
04 Oct
- 07 Oct
Southwest Airlines
$ 157
direct
24 Oct
- 26 Oct
Southwest Airlines
$ 157
direct
24 Oct
- 27 Oct
Southwest Airlines
$ 157
direct
03 Oct
- 06 Oct
Southwest Airlines
$ 157
direct
02 Oct
- 06 Oct
Southwest Airlines
$ 157
direct
21 Oct
- 27 Oct
Southwest Airlines
$ 157
direct
31 Oct
- 03 Nov
Southwest Airlines
$ 157
direct
30 Oct
- 03 Nov
Southwest Airlines
$ 157
direct
28 Oct
- 03 Nov
Southwest Airlines
$ 157
direct
25 Oct
- 01 Nov
Southwest Airlines
$ 157
direct
29 Oct
- 05 Nov
Southwest Airlines
$ 157
direct
27 Oct
- 01 Nov
Southwest Airlines
$ 187
direct
Also check the deals for one-way flights from Boston to Chicago 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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