Flights from Boston Airport (BOS) to Chicago Midway Airport Airport (MDW)

To see all airliners that offer flights between Logan International and Midway please see the table below.

Flights Chart

Airliner	Mo	Tu	We	Th	Fr	Sa	Su	First Flight	Last Flight	Flights
Southwest Airlines	3	3	3	3	3	4	4	05:45	20:20	VIEW FLIGHTS
NetJets	1	0	0	0	0	0	0	16:13	16:13	VIEW FLIGHTS
Executive Jet Management	1	0	0	0	0	0	0	15:00	15:00	VIEW FLIGHTS

Southwest Airlines offer the highest number of flights for this route with departures times between 05:45 and 20:20.

If you wish to book your flight with Southwest Airlines then we advise you book direct from their website at www.southwest.com/?ref=southwestairlines.com. The best discounts can only be obtained from their website.

The flight time for the selected route vary based on the month you will travel, but below we has summarised the most common times they will fly. We recommend you only take these times as guidance and check with appropriate airline for the exact times for the date you depart.

Flights Time In WeekDays

Day	Flight Times	Flights
Monday	05:45 Airline Flight  No Southwest Airlines WN576 09:35 Airline Flight  No Southwest Airlines WN2320 15:00 Airline Flight  No Executive Jet Management EJM377 16:13 Airline Flight  No NetJets EJM377 16:40 Airline Flight  No Southwest Airlines WN3726	VIEW FLIGHTS
Tuesday	05:50 Airline Flight  No Southwest Airlines WN3726 14:05 Airline Flight  No Southwest Airlines WN576 17:35 Airline Flight  No Southwest Airlines WN1371	VIEW FLIGHTS
Wednesday	05:50 Airline Flight  No Southwest Airlines WN3726 14:05 Airline Flight  No Southwest Airlines WN576 17:35 Airline Flight  No Southwest Airlines WN1371	VIEW FLIGHTS
Thursday	05:45 Airline Flight  No Southwest Airlines WN576 09:35 Airline Flight  No Southwest Airlines WN2320 16:40 Airline Flight  No Southwest Airlines WN3726	VIEW FLIGHTS
Friday	05:45 Airline Flight  No Southwest Airlines WN576 09:35 Airline Flight  No Southwest Airlines WN2320 16:40 Airline Flight  No Southwest Airlines WN3726	VIEW FLIGHTS
Saturday	06:20 Airline Flight  No Southwest Airlines WN576 09:00 Airline Flight  No Southwest Airlines WN2320 15:15 Airline Flight  No Southwest Airlines WN277 17:45 Airline Flight  No Southwest Airlines WN3726	VIEW FLIGHTS
Sunday	07:40 Airline Flight  No Southwest Airlines WN576 12:40 Airline Flight  No Southwest Airlines WN277 17:15 Airline Flight  No Southwest Airlines WN2190 20:20 Airline Flight  No Southwest Airlines WN4396	VIEW FLIGHTS

If the airlines stated don’t offer flights that suite your travel times, you could look at alternative options. Below we have summarised flights from alternative departures airports and flights that are not direct.

Alternative Direct Routes

Route	Stops	Distance	Flying Time
Nantucket to Chicago Midway	0		2 Hours 33 Minutes
Windsor Locks to Chicago Midway	0		2 Hours 17 Minutes
Bedford Hanscom to Chicago Midway	0		2 Hours 25 Minutes
Westhampton to Chicago Midway	0		2 Hours 18 Minutes
Manchester boston Regional to Chicago Midway	0		2 Hours 24 Minutes
Pittsfield to Chicago Midway	0		2 Hours 13 Minutes
Providence to Chicago Midway	0		2 Hours 24 Minutes

Before you start your journey remember to check you have all your documents; in particular, your passport and flight tickets. You will be surprised at the amount of people of forget these!