Frontier Airlines
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United States
Orlando International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Orlando to Chicago. The full flight schedule below gives an overview of all non-stop flights from MCO 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.
In total there are 2 airlines operating nonstop flights from Orlando MCO to Chicago MDW. 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 MCO MDW flight schedule.
Flights from MCO to MDW are operated 49 times a week, with an average of 7 flights per day. Departure times vary between 05:25 - 22:55. The earliest flight departs at 05:25, 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 Orlando to Chicago takes 2 hours and 59 minutes. The flight distance between Orlando and Chicago is 990 miles (or 1,593 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 49 flights per week flying from Orlando to Chicago (as of April 2026).
2 hours and 59 minutes is the average flight time from Orlando to Chicago.
The distance from Orlando to Chicago is 990 miles (1,593 kilometers).
Frontier Airlines and Southwest Airlines are flying nonstop from Orlando to Chicago.
There are no alliances flying direct from Orlando to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Orlando to Chicago:
The earliest flight departs at 05:25 from Orlando and arrives at 07:21 at Chicago.
The latest flight departs at 22:55 from Orlando and arrives at 00:50 at Chicago.
990 miles (1,593 km) · 2h 59m
05:25
07:21
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
05:30
07:26
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
06:00
07:59
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
06:05
08:04
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
06:05
08:04
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
06:45
08:40
Southwest Airlines
WN 2300
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:05
09:00
Southwest Airlines
WN 3142
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:10
09:10
Southwest Airlines
WN 2300
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:15
09:15
Southwest Airlines
WN 2300
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:15
09:10
Southwest Airlines
WN 3142
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:20
09:15
Southwest Airlines
WN 3142
Southwest Airlines
Boeing 757
Y
W
J
F
07:20
09:15
Southwest Airlines
WN 3142
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:35
10:30
Southwest Airlines
WN 2540
Southwest Airlines
Boeing 757
Y
W
J
F
08:55
10:45
Southwest Airlines
WN 2619
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:10
11:00
Southwest Airlines
WN 2950
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:05
12:00
Southwest Airlines
WN 1669
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:10
12:00
Southwest Airlines
WN 2619
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
10:15
12:10
Southwest Airlines
WN 2540
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
10:15
12:10
Southwest Airlines
WN 2619
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
10:35
12:25
Southwest Airlines
WN 2619
Southwest Airlines
Boeing 757
Y
W
J
F
11:40
13:35
Southwest Airlines
WN 3862
Southwest Airlines
Boeing 757
Y
W
J
F
11:40
13:30
Southwest Airlines
WN 3144
Southwest Airlines
Boeing 757
Y
W
J
F
11:55
13:45
Southwest Airlines
WN 3783
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:15
14:10
Southwest Airlines
WN 3291
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:30
14:20
Southwest Airlines
WN 1250
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:45
14:40
Southwest Airlines
WN 1669
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:50
14:45
Southwest Airlines
WN 1739
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:55
15:50
Southwest Airlines
WN 3862
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:00
16:00
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
14:13
16:13
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
14:25
16:15
Southwest Airlines
WN 3841
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:50
16:45
Southwest Airlines
WN 3862
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:15
17:05
Southwest Airlines
WN 3269
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:40
17:30
Southwest Airlines
WN 3269
Southwest Airlines
Boeing 757
Y
W
J
F
15:55
17:45
Southwest Airlines
WN 3269
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:55
17:54
Frontier Airlines
F9 1457
Frontier Airlines
Airbus A320neo
Y
W
J
F
16:45
18:45
Southwest Airlines
WN 4015
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:55
18:55
Southwest Airlines
WN 3587
Southwest Airlines
Boeing 757
Y
W
J
F
17:00
19:05
Southwest Airlines
WN 4015
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:05
19:00
Southwest Airlines
WN 2046
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:20
19:10
Southwest Airlines
WN 3089
Southwest Airlines
Boeing 757
Y
W
J
F
17:35
19:30
Southwest Airlines
WN 1823
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:50
19:45
Southwest Airlines
WN 2046
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:15
20:15
Southwest Airlines
WN 1254
Southwest Airlines
Boeing 757
Y
W
J
F
18:25
20:25
Southwest Airlines
WN 4015
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:30
20:25
Southwest Airlines
WN 2046
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:35
20:30
Southwest Airlines
WN 2046
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:50
20:40
Southwest Airlines
WN 1250
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:53
20:52
Frontier Airlines
F9 1457
Frontier Airlines
Airbus A320neo
Y
W
J
F
18:55
20:55
Southwest Airlines
WN 4054
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:15
21:10
Southwest Airlines
WN 3155
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:22
21:21
Frontier Airlines
F9 1457
Frontier Airlines
Airbus A320neo
Y
W
J
F
19:35
21:25
Southwest Airlines
WN 1250
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:55
21:55
Southwest Airlines
WN 3155
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:55
21:50
Southwest Airlines
WN 1250
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
19:59
21:58
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
20:00
22:00
Southwest Airlines
WN 3155
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
20:45
22:35
Southwest Airlines
WN 138
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:00
23:00
Frontier Airlines
F9 3853
Frontier Airlines
Airbus A320neo
Y
W
J
F
21:05
23:05
Frontier Airlines
F9 1535
Frontier Airlines
Airbus A320neo
Y
W
J
F
21:55
23:50
Southwest Airlines
WN 1780
Southwest Airlines
Boeing 757
Y
W
J
F
22:00
23:57
Frontier Airlines
F9 1535
Frontier Airlines
Airbus A320neo
Y
W
J
F
22:10
00:05
Southwest Airlines
WN 138
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
22:50
00:45
Southwest Airlines
WN 416
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
22:55
00:50
Southwest Airlines
WN 416
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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