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

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

Return flights

21 Nov - 24 Nov Southwest Airlines direct
12 Nov - 17 Nov Southwest Airlines direct
20 Nov - 25 Nov Southwest Airlines direct
27 Nov - 02 Dec Southwest Airlines direct
01 Nov - 03 Nov Southwest Airlines direct
21 Nov - 23 Nov Southwest Airlines
16 Nov - 21 Nov Southwest Airlines
07 Nov - 11 Nov Southwest Airlines
27 Nov - 01 Dec Southwest Airlines
27 Nov - 29 Nov Southwest Airlines
25 Nov - 28 Nov Delta
27 Nov - 30 Nov Southwest Airlines direct

Also check the deals for one-way flights from Boston to Chicago in November.

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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