Southwest Airlines
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United States
Midway International Airport
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United States
Logan International Airport
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Scan through all non-stop flights from Chicago to Boston. The full flight schedule below gives an overview of all non-stop flights from MDW to BOS, 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, Boston 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 Boston 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 Chicago MDW to Boston BOS, 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 MDW BOS flight schedule.
Flights from MDW to BOS are operated 27 times a week, with an average of 4 flights per day. Departure times vary between 05:15 - 19:35. The earliest flight departs at 05:15, the last flight departs at 19:35. 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 Chicago to Boston takes 2 hours and 15 minutes. The flight distance between Chicago and Boston is 858 miles (or 1,381 km).
There is 1 airport in Boston: Logan International Airport (BOS).
There are 27 flights per week flying from Chicago to Boston (as of April 2026).
2 hours and 15 minutes is the average flight time from Chicago to Boston.
The distance from Chicago to Boston is 858 miles (1,381 kilometers).
Southwest Airlines is the only airline flying nonstop from Chicago to Boston.
There are no alliances flying direct from Chicago to Boston at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to Boston:
The earliest flight departs at 05:15 from Chicago and arrives at 08:25 at Boston.
The latest flight departs at 19:35 from Chicago and arrives at 22:50 at Boston.
858 miles (1,381 km) · 2h 15m
07:40
10:55
Southwest Airlines
WN 3352
Southwest Airlines
Boeing 757
Y
W
J
F
07:40
10:55
Southwest Airlines
WN 3352
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:40
10:55
Southwest Airlines
WN 3737
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:40
10:55
Southwest Airlines
WN 3737
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:45
11:00
Southwest Airlines
WN 1800
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:55
11:10
Southwest Airlines
WN 3352
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
09:25
12:40
Southwest Airlines
WN 164
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:40
12:55
Southwest Airlines
WN 1800
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:25
14:45
Southwest Airlines
WN 2619
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:45
16:05
Southwest Airlines
WN 3737
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:30
16:40
Southwest Airlines
WN 1716
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:40
16:50
Southwest Airlines
WN 1716
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
13:55
17:10
Southwest Airlines
WN 1280
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:05
17:20
Southwest Airlines
WN 1280
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:45
18:00
Southwest Airlines
WN 1740
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:15
18:35
Southwest Airlines
WN 1280
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:30
18:45
Southwest Airlines
WN 1740
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:30
18:45
Southwest Airlines
WN 1280
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
15:45
19:00
Southwest Airlines
WN 1740
Southwest Airlines
Boeing 757
Y
W
J
F
18:00
21:20
Southwest Airlines
WN 2392
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:05
21:25
Southwest Airlines
WN 2392
Southwest Airlines
Boeing 757
Y
W
J
F
18:45
22:00
Southwest Airlines
WN 1930
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:45
22:05
Southwest Airlines
WN 2392
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:00
22:15
Southwest Airlines
WN 1930
Southwest Airlines
Boeing 757
Y
W
J
F
19:00
22:20
Southwest Airlines
WN 2392
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:30
22:45
Southwest Airlines
WN 3587
Southwest Airlines
Boeing 757
Y
W
J
F
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