Southwest Airlines
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Bradley International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Hartford to Chicago. The full flight schedule below gives an overview of all non-stop flights from BDL 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 Hartford BDL 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 BDL MDW flight schedule.
Flights from BDL to MDW are operated 18 times a week, with an average of 3 flights per day. Departure times vary between 06:50 - 19:20. The earliest flight departs at 06:50, the last flight departs at 19:20. 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 Hartford to Chicago takes 2 hours and 30 minutes. The flight distance between Hartford and Chicago is 774 miles (or 1,246 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 18 flights per week flying from Hartford to Chicago (as of April 2026).
2 hours and 30 minutes is the average flight time from Hartford to Chicago.
The distance from Hartford to Chicago is 774 miles (1,246 kilometers).
Southwest Airlines is the only airline flying nonstop from Hartford to Chicago.
There are no alliances flying direct from Hartford to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Hartford to Chicago:
The earliest flight departs at 06:50 from Hartford and arrives at 08:15 at Chicago.
The latest flight departs at 19:20 from Hartford and arrives at 20:45 at Chicago.
774 miles (1,246 km) · 2h 30m
07:00
08:25
Southwest Airlines
WN 2108
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:15
08:45
Southwest Airlines
WN 984
Southwest Airlines
Boeing 757
Y
W
J
F
07:30
09:00
Southwest Airlines
WN 984
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:35
09:05
Southwest Airlines
WN 984
Southwest Airlines
Boeing 757
Y
W
J
F
07:45
09:05
Southwest Airlines
WN 2108
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:45
09:05
Southwest Airlines
WN 2108
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:50
09:15
Southwest Airlines
WN 2108
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:20
12:50
Southwest Airlines
WN 168
Southwest Airlines
Boeing 757
Y
W
J
F
11:40
13:05
Southwest Airlines
WN 202
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:20
13:50
Southwest Airlines
WN 312
Southwest Airlines
Boeing 757
Y
W
J
F
12:25
13:50
Southwest Airlines
WN 202
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:45
18:15
Southwest Airlines
WN 2390
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:10
19:40
Southwest Airlines
WN 2390
Southwest Airlines
Boeing 757
Y
W
J
F
18:20
19:50
Southwest Airlines
WN 588
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:45
20:10
Southwest Airlines
WN 2670
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:05
20:35
Southwest Airlines
WN 2390
Southwest Airlines
Boeing 757
Y
W
J
F
19:10
20:40
Southwest Airlines
WN 2390
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:20
20:45
Southwest Airlines
WN 588
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
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