Southwest Airlines
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Midway International Airport
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Scan through all non-stop flights from Boston to Chicago. The full flight schedule below gives an overview of all non-stop flights from BOS to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Boston BOS to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their BOS MDW flight schedule.
Flights from BOS to MDW are operated 34 times a week, with an average of 5 flights per day. Departure times vary between 05:15 - 22:25. The earliest flight departs at 05:15, the last flight departs at 22:25. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Boston to Chicago takes 2 hours and 35 minutes. The flight distance between Boston and Chicago is 858 miles (or 1,381 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 34 flights per week flying from Boston to Chicago (as of July 2026).
2 hours and 35 minutes is the average flight time from Boston to Chicago.
The distance from Boston to Chicago is 858 miles (1,381 kilometers).
Southwest Airlines is the only airline flying nonstop from Boston to Chicago.
There are no alliances flying direct from Boston to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Boston to Chicago:
The earliest flight departs at 05:15 from Boston and arrives at 06:50 at Chicago.
The latest flight departs at 22:25 from Boston and arrives at 00:15 at Chicago.
858 miles (1,381 km) · 2h 35m
05:15
06:50
Southwest Airlines
WN 1579
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
05:20
06:55
Southwest Airlines
WN 3239
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
05:25
07:00
Southwest Airlines
WN 3239
Southwest Airlines
Boeing 737-700
Y
W
J
F
05:35
07:10
Southwest Airlines
WN 3054
Southwest Airlines
Boeing 737-700
Y
W
J
F
07:20
09:00
Southwest Airlines
WN 745
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:30
09:10
Southwest Airlines
WN 745
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:45
09:25
Southwest Airlines
WN 1864
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:55
09:30
Southwest Airlines
WN 745
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:55
14:30
Southwest Airlines
WN 746
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
13:10
14:45
Southwest Airlines
WN 746
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
13:25
15:05
Southwest Airlines
WN 320
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:10
15:50
Southwest Airlines
WN 746
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:25
17:00
Southwest Airlines
WN 1496
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:45
17:30
Southwest Airlines
WN 4106
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
16:45
18:35
Southwest Airlines
WN 4106
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:45
18:35
Southwest Airlines
WN 2777
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:30
19:25
Southwest Airlines
WN 3911
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:40
19:30
Southwest Airlines
WN 3911
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:45
19:35
Southwest Airlines
WN 3911
Southwest Airlines
Boeing 737-700
Y
W
J
F
18:45
20:35
Southwest Airlines
WN 3911
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:05
20:55
Southwest Airlines
WN 3287
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
22:05
23:50
Southwest Airlines
WN 585
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
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