Southwest Airlines
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Midway International Airport
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Scan through all non-stop flights from Dallas to Chicago. The full flight schedule below gives an overview of all non-stop flights from DAL 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 Dallas DAL 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 DAL MDW flight schedule.
Flights from DAL to MDW are operated 51 times a week, with an average of 7 flights per day. Departure times vary between 06:00 - 22:55. The earliest flight departs at 06:00, the last flight departs at 22:55. 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 Dallas to Chicago takes 2 hours and 10 minutes. The flight distance between Dallas and Chicago is 793 miles (or 1,276 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 51 flights per week flying from Dallas to Chicago (as of July 2026).
2 hours and 10 minutes is the average flight time from Dallas to Chicago.
The distance from Dallas to Chicago is 793 miles (1,276 kilometers).
Southwest Airlines is the only airline flying nonstop from Dallas to Chicago.
There are no alliances flying direct from Dallas to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Dallas to Chicago:
The earliest flight departs at 06:00 from Dallas and arrives at 08:15 at Chicago.
The latest flight departs at 22:55 from Dallas and arrives at 01:05 at Chicago.
793 miles (1,276 km) · 2h 10m
06:00
08:15
Southwest Airlines
WN 1355
Southwest Airlines
Boeing 737 MAX 8
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06:00
08:15
Southwest Airlines
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Southwest Airlines
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06:05
08:20
Southwest Airlines
WN 2337
Southwest Airlines
Boeing 737 MAX 8
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06:10
08:25
Southwest Airlines
WN 1355
Southwest Airlines
Boeing 737-800 (winglets)
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07:15
09:30
Southwest Airlines
WN 1307
Southwest Airlines
Boeing 737 MAX 8
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08:30
10:45
Southwest Airlines
WN 1356
Southwest Airlines
Boeing 737-700
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08:30
10:45
Southwest Airlines
WN 1356
Southwest Airlines
Boeing 737-700
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09:15
11:30
Southwest Airlines
WN 2744
Southwest Airlines
Boeing 737 MAX 8
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09:40
11:55
Southwest Airlines
WN 595
Southwest Airlines
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09:45
12:00
Southwest Airlines
WN 1517
Southwest Airlines
Boeing 737 MAX 8
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10:00
12:15
Southwest Airlines
WN 8
Southwest Airlines
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10:05
12:20
Southwest Airlines
WN 1357
Southwest Airlines
Boeing 737-800 (winglets)
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12:05
14:15
Southwest Airlines
WN 1032
Southwest Airlines
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12:25
14:40
Southwest Airlines
WN 1357
Southwest Airlines
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12:30
14:45
Southwest Airlines
WN 298
Southwest Airlines
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13:10
15:25
Southwest Airlines
WN 1358
Southwest Airlines
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14:05
16:20
Southwest Airlines
WN 1358
Southwest Airlines
Boeing 737-800 (winglets)
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14:35
16:50
Southwest Airlines
WN 1006
Southwest Airlines
Boeing 737-700
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15:00
17:15
Southwest Airlines
WN 1358
Southwest Airlines
Boeing 737-700
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15:00
17:15
Southwest Airlines
WN 1358
Southwest Airlines
Boeing 737 MAX 8
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15:00
17:15
Southwest Airlines
WN 1358
Southwest Airlines
Boeing 737-700
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15:50
18:05
Southwest Airlines
WN 1359
Southwest Airlines
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16:05
18:15
Southwest Airlines
WN 4388
Southwest Airlines
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16:30
18:40
Southwest Airlines
WN 5
Southwest Airlines
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16:40
18:55
Southwest Airlines
WN 1448
Southwest Airlines
Boeing 737-800 (winglets)
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16:50
19:05
Southwest Airlines
WN 36
Southwest Airlines
Boeing 737-800 (winglets)
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18:30
20:40
Southwest Airlines
WN 987
Southwest Airlines
Boeing 737 MAX 8
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18:45
21:00
Southwest Airlines
WN 107
Southwest Airlines
Boeing 737-800 (winglets)
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19:35
21:50
Southwest Airlines
WN 4258
Southwest Airlines
Boeing 737-700
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19:50
22:00
Southwest Airlines
WN 107
Southwest Airlines
Boeing 737-800 (winglets)
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19:50
22:00
Southwest Airlines
WN 2103
Southwest Airlines
Boeing 737-800 (winglets)
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19:50
22:05
Southwest Airlines
WN 107
Southwest Airlines
Boeing 737-800 (winglets)
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21:00
23:15
Southwest Airlines
WN 1189
Southwest Airlines
Boeing 737 MAX 8
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21:25
23:40
Southwest Airlines
WN 1151
Southwest Airlines
Boeing 737-700
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21:55
00:05
Southwest Airlines
WN 1359
Southwest Airlines
Boeing 737 MAX 8
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21:55
00:10
Southwest Airlines
WN 1359
Southwest Airlines
Boeing 737-700
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22:50
01:00
Southwest Airlines
WN 1359
Southwest Airlines
Boeing 737 MAX 8
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22:50
01:05
Southwest Airlines
WN 1359
Southwest Airlines
Boeing 737 MAX 8
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