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	5	4	4	5	5	4	4	06:50	22:00	VIEW FLIGHTS
Flexjet	0	1	0	1	0	0	0	11:30	23:28	VIEW FLIGHTS

Southwest Airlines offer the highest number of flights for this route with departures times between 06:50 and 22:00.

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	08:25 Airline Flight  No Southwest Airlines WN4218 08:50 Airline Flight  No Southwest Airlines WN3338 14:45 Airline Flight  No Southwest Airlines WN573 19:05 Airline Flight  No Southwest Airlines WN2376 22:00 Airline Flight  No Southwest Airlines WN2689	VIEW FLIGHTS
Tuesday	07:20 Airline Flight  No Southwest Airlines WN4218 11:15 Airline Flight  No Southwest Airlines WN4149 15:25 Airline Flight  No Southwest Airlines WN573 17:25 Airline Flight  No Southwest Airlines WN2376 23:28 Airline Flight  No Flexjet LXJ572	VIEW FLIGHTS
Wednesday	08:55 Airline Flight  No Southwest Airlines WN4218 11:15 Airline Flight  No Southwest Airlines WN4149 17:10 Airline Flight  No Southwest Airlines WN573 17:25 Airline Flight  No Southwest Airlines WN2376	VIEW FLIGHTS
Thursday	08:25 Airline Flight  No Southwest Airlines WN4218 09:00 Airline Flight  No Southwest Airlines WN3338 11:30 Airline Flight  No Flexjet LXJ417 14:45 Airline Flight  No Southwest Airlines WN573 17:25 Airline Flight  No Southwest Airlines WN2376 22:00 Airline Flight  No Southwest Airlines WN2689	VIEW FLIGHTS
Friday	06:50 Airline Flight  No Southwest Airlines WN4218 08:50 Airline Flight  No Southwest Airlines WN3338 13:10 Airline Flight  No Southwest Airlines WN573 19:05 Airline Flight  No Southwest Airlines WN2376 20:25 Airline Flight  No Southwest Airlines WN2689	VIEW FLIGHTS
Saturday	06:20 Airline Flight  No Southwest Airlines WN4218 11:55 Airline Flight  No Southwest Airlines WN497 12:50 Airline Flight  No Southwest Airlines WN573 16:45 Airline Flight  No Southwest Airlines WN2376	VIEW FLIGHTS
Sunday	09:05 Airline Flight  No Southwest Airlines WN4218 12:55 Airline Flight  No Southwest Airlines WN4279 15:55 Airline Flight  No Southwest Airlines WN573 20:40 Airline Flight  No Southwest Airlines WN2689	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
East Hampton to Chicago Midway	0		2 Hours 20 Minutes
New Haven to Chicago Midway	0		2 Hours 16 Minutes
White River to Chicago Midway	0		2 Hours 19 Minutes
Manchester boston Regional to Chicago Midway	0		2 Hours 24 Minutes
Oxford Waterbury oxford to Chicago Midway	0		2 Hours 14 Minutes
Provincetown to Chicago Midway	0		2 Hours 31 Minutes
Providence to Chicago Midway	0		2 Hours 24 Minutes
Portland to Chicago Midway	0		2 Hours 30 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!