Flights Boston to Chicago BOS to MDW

Boston to Chicago Flights

There are 59 flights from Boston (BOS) to Chicago (MDW) airport operated by 3 airlines. Below you can see the 30 most recent flights from BOS to MDW:

Flight	Airline	Last Seen	Departure	Arrival
WN585	Southwest Airlines	Jun 14	22:05	23:45	See More >
WN3239	Southwest Airlines	Today	05:25	07:00	See More >
WN745	Southwest Airlines	Today	07:30	09:10	See More >
WN746	Southwest Airlines	Today	13:10	14:45	See More >
WN2777	Southwest Airlines	Jun 14	16:45	18:35	See More >
WN3287	Southwest Airlines	Jun 14	19:05	20:55	See More >
WN3911	Southwest Airlines	Jun 13	17:45	19:35	See More >
WN4106	Southwest Airlines	Jun 12	16:45	18:35	See More >
WN3054	Southwest Airlines	Jun 10	05:35	07:10	See More >
WN320	Southwest Airlines	Jun 10	13:25	15:05	See More >
WN961	Southwest Airlines	Jun 03	07:20	09:05	See More >
WN776	Southwest Airlines	Jun 03	10:45	12:25	See More >
WN898	Southwest Airlines	Jun 03	14:25	16:05	See More >
WN3665	Southwest Airlines	Jun 03	18:20	20:10	See More >
WN3285	Southwest Airlines	May 31	06:10	07:55	See More >
WN4618	Southwest Airlines	May 31	18:50	20:40	See More >
WN2540	Southwest Airlines	May 30	09:25	11:05	See More >
DL8882	Delta Air Lines	May 24	17:50	19:18	See More >
WN833	Southwest Airlines	Apr 2026	07:15	09:10	See More >
WN527	Southwest Airlines	Apr 2026	11:50	13:40	See More >
WN3514	Southwest Airlines	Apr 2026	15:10	16:55	See More >
WN1266	Southwest Airlines	Apr 2026	18:25	20:25	See More >
WN699	Southwest Airlines	Mar 2026	05:30	07:20	See More >
WN701	Southwest Airlines	Mar 2026	14:40	16:30	See More >
WN700	Southwest Airlines	Mar 2026	13:55	15:45	See More >
B69001	JetBlue Airways	Jan 2026	10:30	10:11	See More >
WN2012	Southwest Airlines	Jan 2026	05:15	07:00	See More >
WN1432	Southwest Airlines	Jan 2026	13:45	15:30	See More >
WN1030	Southwest Airlines	Jan 2026	18:55	20:45	See More >
WN3725	Southwest Airlines	Jan 2026	19:55	21:40	See More >