Southwest Airlines
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United States
Midway International Airport
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United States
Orlando International Airport
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Scan through all non-stop flights from Chicago to Orlando. The full flight schedule below gives an overview of all non-stop flights from MDW to MCO, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Orlando is a humid subtropical or warm-temperate destination, featuring hot, humid summers with temperatures typically around 30°C (86°F) and mild to cool winters. The region is known for consistent rainfall throughout the year, peaking in summer. The area is known for its vibrant urban energy, diverse landscapes, and numerous outdoor activities.
You can visit Orlando any time of the year, but the best months to explore are from to and from to .
In total there are 2 airlines operating nonstop flights from Chicago MDW to Orlando MCO. 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 MCO flight schedule.
Flights from MDW to MCO are operated 31 times a week, with an average of 4 flights per day. Departure times vary between 05:00 - 20:50. The earliest flight departs at 05:00, the last flight departs at 20:50. 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 Orlando takes 2 hours and 50 minutes. The flight distance between Chicago and Orlando is 990 miles (or 1,593 km).
There are 2 airports in Orlando: Orlando International Airport (MCO) and Orlando Sanford International Airport (SFB).
There are 31 flights per week flying from Chicago to Orlando (as of August 2026).
2 hours and 50 minutes is the average flight time from Chicago to Orlando.
The distance from Chicago to Orlando is 990 miles (1,593 kilometers).
Frontier Airlines and Southwest Airlines are flying nonstop from Chicago to Orlando.
There are no alliances flying direct from Chicago to Orlando at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to Orlando:
The earliest flight departs at 05:00 from Chicago and arrives at 08:30 at Orlando.
The latest flight departs at 20:50 from Chicago and arrives at 00:25 at Orlando.
990 miles (1,593 km) · 2h 50m
05:00
08:30
Southwest Airlines
WN 801
Southwest Airlines
Boeing 737-700
Y
W
J
F
05:00
08:30
Southwest Airlines
WN 2758
Southwest Airlines
Boeing 737-700
Y
W
J
F
05:00
08:30
Southwest Airlines
WN 801
Southwest Airlines
Boeing 737-700
Y
W
J
F
05:10
08:40
Southwest Airlines
WN 2758
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:15
09:45
Southwest Airlines
WN 2758
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:25
10:55
Southwest Airlines
WN 65
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:25
10:55
Southwest Airlines
WN 491
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:25
10:55
Southwest Airlines
WN 238
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:45
11:20
Southwest Airlines
WN 636
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:05
11:50
Southwest Airlines
WN 3060
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:30
12:15
Southwest Airlines
WN 636
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:10
12:45
Southwest Airlines
WN 3245
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:40
13:15
Southwest Airlines
WN 2764
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:15
14:50
Southwest Airlines
WN 1854
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:20
16:00
Southwest Airlines
WN 376
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
14:15
17:50
Southwest Airlines
WN 4933
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:55
18:30
Southwest Airlines
WN 2764
Southwest Airlines
Boeing 737-700
Y
W
J
F
15:40
19:15
Southwest Airlines
WN 4933
Southwest Airlines
Boeing 737-700
Y
W
J
F
15:40
19:15
Southwest Airlines
WN 4933
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:00
21:40
Southwest Airlines
WN 4322
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:00
21:40
Southwest Airlines
WN 260
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:20
22:00
Southwest Airlines
WN 65
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:20
22:00
Southwest Airlines
WN 491
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:50
23:20
Southwest Airlines
WN 2763
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
20:05
23:35
Southwest Airlines
WN 1417
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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