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
23 Oct - 26 Oct Frontier Airlines
16 Oct - 19 Oct Frontier Airlines
15 Oct - 21 Oct Southwest Airlines direct
04 Oct - 07 Oct Southwest Airlines direct
24 Oct - 26 Oct Southwest Airlines direct
24 Oct - 27 Oct Southwest Airlines direct
03 Oct - 06 Oct Southwest Airlines direct
02 Oct - 06 Oct Southwest Airlines direct
21 Oct - 27 Oct Southwest Airlines direct
31 Oct - 03 Nov Southwest Airlines direct
30 Oct - 03 Nov Southwest Airlines direct
28 Oct - 03 Nov Southwest Airlines direct
25 Oct - 01 Nov Southwest Airlines direct
29 Oct - 05 Nov Southwest Airlines direct
27 Oct - 01 Nov Southwest Airlines direct

Also check the deals for one-way 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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.