Orlando (MCO) to Chicago/Midway (MDW) Flight Schedule

Flight Orlando(MCO) to Midway(MDW)
CHANGE DIRECTION

Orlando International Airport Chicago Midway International Airport
MCO : Orlando , United States MDW : Chicago , United States
UTC-4(DST) UTC-5(DST)

Orlando to Midway Flight Schedule(September 2025)

Flight from Orlando(MCO) to Midway(MDW) is operated by 2 airlines : Southwest Airlines (WN),Frontier Airlines (F9). You can check flight schedules, flight duration, and aircraft types.

Change Direction(MDW to MCO)

Orlando (MCO) to Chicago/Midway (MDW) Flight Schedule

LastUpdate : 2025/09/01 06:00

Flight Schedule on September 2025 , Direct flight departure from Orlando with all airlines , flight number, flight duration, aircraft type.

September 2025
Mo Tu We Th Fr Sa Su Mo Tu We Th Fr Sa Su Mo Tu We Th Fr Sa Su Mo Tu We Th Fr Sa Su Mo Tu
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  • Southwest Airlines [ Show / Hide ]
  • Frontier Airlines [ Show / Hide ]
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Change Direction(MDW to MCO)
Flight Number / Airline Departure Time Arrival Time Flight Duration Operating Days Aircraft Type Airfare / Tickets
F93853
Frontier Airlines 		13:33 15:29 2h56m
M------ (Sep 1)
A320neo Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
07:00 08:53 2h53m
----F-- (Sep 5, Sep 12, Sep 19, Sep 26)
A320neo
07:25 09:18 2h53m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
A320neo
05:35 07:23 2h48m
M------ (Sep 8, Sep 15, Sep 22, Sep 29)
A320neo
08:00 09:51 2h51m
-----S- (Sep 13, Sep 20, Sep 27)
A320neo
Codeshare flight ▼
WN1053
Southwest Airlines 		06:20 08:05 2h45m
M------ (Sep 29)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN147
Southwest Airlines 		07:15 09:00 2h45m
-----S- (Sep 6, Sep 13, Sep 20, Sep 27)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
06:50 08:35 2h45m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
737-800 (WL)
WN3591
Southwest Airlines 		10:30 12:15 2h45m
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
07:10 08:55 2h45m
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
737-8-MAX
10:30 12:15 2h45m
M------ (Sep 29)
737-700 (WL)
WN836
Southwest Airlines 		07:15 10:35 4h20m
1 Transfer
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26, Sep 29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1570
Southwest Airlines 		07:35 09:20 2h45m
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26, Sep 29)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN5963
Southwest Airlines 		07:55 09:40 2h45m
------S (Sep 14)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN6034
Southwest Airlines 		08:45 10:30 2h45m
------S (Sep 14)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN4077
Southwest Airlines 		08:55 12:10 4h15m
1 Transfer
------S (Sep 7, Sep 14, Sep 21, Sep 28)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
09:40 12:50 4h10m
1 Transfer
M------ (Sep 29)
WN1565
Southwest Airlines 		09:00 12:05 4h5m
1 Transfer
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1488
Southwest Airlines 		09:15 13:50 5h35m
1 Transfer
------S (Sep 7, Sep 14, Sep 21, Sep 28)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3546
Southwest Airlines 		09:25 14:40 6h15m
2 Transfers
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN951
Southwest Airlines 		09:50 13:55 5h5m
1 Transfer
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26, Sep 29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1373
Southwest Airlines 		12:20 14:05 2h45m
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
10:05 11:50 2h45m
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
737-8-MAX
12:10 13:50 2h40m
-----S- (Sep 6, Sep 13, Sep 20, Sep 27)
737-800 (WL)
10:05 11:50 2h45m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
737-8-MAX
12:20 14:05 2h45m
M------ (Sep 29)
737-800 (WL)
WN1104
Southwest Airlines 		10:40 14:45 5h5m
1 Transfer
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26, Sep 29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3870
Southwest Airlines 		11:25 13:05 2h40m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2409
Southwest Airlines 		11:45 13:25 2h40m
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1687
Southwest Airlines 		11:50 15:35 4h45m
1 Transfer
-----S- (Sep 6, Sep 13, Sep 20, Sep 27)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1766
Southwest Airlines 		12:00 15:10 4h10m
1 Transfer
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN818
Southwest Airlines 		12:00 16:25 5h25m
1 Transfer
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2303
Southwest Airlines 		14:25 19:00 5h35m
1 Transfer
-----S- (Sep 6, Sep 13, Sep 20, Sep 27)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1500
Southwest Airlines 		15:00 16:45 2h45m
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24, Sep 30)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN935
Southwest Airlines 		15:30 17:15 2h45m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1186
Southwest Airlines 		15:35 17:20 2h45m
-----S- (Sep 6, Sep 13, Sep 20, Sep 27)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1972
Southwest Airlines 		16:25 18:15 2h50m
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
17:00 18:50 2h50m
-----S- (Sep 6, Sep 13, Sep 20, Sep 27)
737-700 (WL)
18:20 20:10 2h50m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
737-800 (WL)
16:25 18:15 2h50m
M------ (Sep 29)
737-700 (WL)
WN3595
Southwest Airlines 		17:40 19:25 2h45m
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26, Sep 29)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN748
Southwest Airlines 		20:40 22:25 2h45m
M--TF-- (Sep 1, Sep 4–5, Sep 8, Sep 11–12, Sep 15, Sep 18–19, Sep 22, Sep 25–26)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
19:55 21:40 2h45m
-TW---- (Sep 2–3, Sep 9–10, Sep 16–17, Sep 23–24)
737-700 (WL)
18:30 20:20 2h50m
-----S- (Sep 6, Sep 13, Sep 20, Sep 27)
737-700 (WL)
19:40 21:25 2h45m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
737-800 (WL)
20:40 22:25 2h45m
M------ (Sep 29)
737-800 (WL)
19:55 21:40 2h45m
-T----- (Sep 30)
737-700 (WL)
WN3277
Southwest Airlines 		22:10 23:55 2h45m
------S (Sep 7, Sep 14, Sep 21, Sep 28)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
Change Direction(MDW to MCO)
Flight schedules as of September 01, 2025, 06:00 AM(OAG data). Schedules may change without notice, so please check with airlines before booking. Refer to FlyTeam's terms of use before proceeding. Some airlines and flight numbers may not be displayed.

FAQ : Orlando to Chicago/Midway

How many airlines fly from Orlando to Chicago ?
As of September 2025, 2 airlines operate direct flights from Orlando (MCO) to Chicago/Midway (MDW) : Southwest Airlines , Frontier Airlines.
How far is it from Orlando to Chicago?
The distance between Orlando (MCO) to Chicago/Midway (MDW) is approximately 990 miles(1,600km) by air.
What is the time difference between Orlando to Chicago?
The time difference between Orlando International Airport(Orlando) and Chicago Midway International Airport(Chicago) is -1 hour. Chicago is 1 hour behind Orlando.Orlando is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.Chicago is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.