Orlando (MCO) to Chicago/Midway (MDW) October 2025 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(October 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 October 2025 , Direct flight departure from Orlando with all airlines , flight number, flight duration, aircraft type.

October 2025
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 We Th Fr
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  • Southwest Airlines [ Show / Hide ]
  • Frontier Airlines [ Show / Hide ]
  • ★ CodeShare [ Show / Hide ]
Change Direction(MDW to MCO)
Flight Number / Airline Departure Time Arrival Time Flight Duration Operating Days Aircraft Type Airfare / Tickets
F93853
Frontier Airlines 		07:00 08:53 2h53m
----F-- (Oct 3)
A320neo Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
08:30 10:21 2h51m
-----S- (Oct 4)
A320neo
07:25 09:18 2h53m
------S (Oct 5)
A320neo
05:35 07:23 2h48m
M------ (Oct 6)
A320neo
07:50 09:47 2h57m
---T--- (Oct 9)
A320neo
14:26 16:20 2h54m
----F-- (Oct 10, Oct 17)
A320neo
13:16 15:11 2h55m
-----S- (Oct 11)
A320neo
09:44 11:39 2h55m
------S (Oct 12)
A320neo
14:34 16:28 2h54m
M------ (Oct 13)
A320neo
08:25 10:21 2h56m
-----S- (Oct 18, Oct 25)
A320neo
09:10 11:05 2h55m
------S (Oct 19)
A320neo
14:26 16:20 2h54m
M---F-- (Oct 20, Oct 24)
A320neo
07:50 09:47 2h57m
---T--- (Oct 23)
A320neo
09:02 10:57 2h55m
------S (Oct 26)
A320neo
14:26 16:20 2h54m
M------ (Oct 27)
A320neo
07:15 09:12 2h57m
---T--- (Oct 30)
A320neo
06:35 08:32 2h57m
----F-- (Oct 31)
A320neo
Codeshare flight ▼
WN3370
Southwest Airlines 		06:35 08:20 2h45m
M--TF-- (Oct 2–3, Oct 6, Oct 9–10)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
07:20 09:10 2h50m
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
737-800 (WL)
06:35 08:20 2h45m
M--TF-- (Oct 13, Oct 16–17, Oct 20, Oct 23–24)
737-8-MAX
WN223
Southwest Airlines 		07:10 09:00 2h50m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
06:50 08:40 2h50m
------S (Oct 5, Oct 12, Oct 19, Oct 26)
737-700 (WL)
WN3591
Southwest Airlines 		07:10 08:55 2h45m
--W---- (Oct 1)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3713
Southwest Airlines 		08:20 10:05 2h45m
---TF-- (Oct 2–3)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
09:20 11:05 2h45m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-800 (WL)
08:20 10:05 2h45m
M--TF-- (Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24)
737-800 (WL)
16:35 18:20 2h45m
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
737-8-MAX
07:40 09:30 2h50m
----F-- (Oct 31)
737-8-MAX
WN364
Southwest Airlines 		08:00 12:40 5h40m
1 Transfer
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2964
Southwest Airlines 		08:50 13:10 5h20m
1 Transfer
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1313
Southwest Airlines 		13:40 16:40 4h0m
1 Transfer
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
08:50 12:10 4h20m
1 Transfer
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
WN1353
Southwest Airlines 		08:55 12:45 4h50m
1 Transfer
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1565
Southwest Airlines 		09:00 12:05 4h5m
1 Transfer
--W---- (Oct 1)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2214
Southwest Airlines 		09:15 13:30 5h15m
1 Transfer
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3082
Southwest Airlines 		09:25 13:45 5h20m
1 Transfer
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3546
Southwest Airlines 		09:25 14:40 6h15m
2 Transfers
--W---- (Oct 1)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1544
Southwest Airlines 		09:30 11:15 2h45m
------S (Oct 5, Oct 12, Oct 19, Oct 26)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
12:15 14:00 2h45m
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
737-8-MAX
WN3346
Southwest Airlines 		10:10 11:55 2h45m
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
09:30 11:15 2h45m
----F-- (Oct 31)
737-8-MAX
WN626
Southwest Airlines 		09:50 11:35 2h45m
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1373
Southwest Airlines 		10:05 11:50 2h45m
--W---- (Oct 1)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3164
Southwest Airlines 		10:15 13:35 4h20m
1 Transfer
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1806
Southwest Airlines 		10:20 12:05 2h45m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
10:55 12:40 2h45m
------S (Oct 5, Oct 12, Oct 19, Oct 26)
737-8-MAX
WN2750
Southwest Airlines 		10:35 13:55 4h20m
1 Transfer
------S (Oct 5, Oct 12, Oct 19, Oct 26)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN737
Southwest Airlines 		11:25 13:15 2h50m
----F-- (Oct 31)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN6581
Southwest Airlines 		11:40 13:30 2h50m
-----S- (Oct 18)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2409
Southwest Airlines 		11:45 13:25 2h40m
--W---- (Oct 1)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1766
Southwest Airlines 		12:00 15:10 4h10m
1 Transfer
--W---- (Oct 1)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN818
Southwest Airlines 		12:00 16:25 5h25m
1 Transfer
--W---- (Oct 1)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3291
Southwest Airlines 		12:10 15:45 4h35m
1 Transfer
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3860
Southwest Airlines 		13:10 14:55 2h45m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
12:25 14:10 2h45m
----F-- (Oct 31)
737-700 (WL)
WN949
Southwest Airlines 		13:10 16:30 4h20m
1 Transfer
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN4131
Southwest Airlines 		13:30 17:40 5h10m
1 Transfer
------S (Oct 5, Oct 12, Oct 19, Oct 26)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3107
Southwest Airlines 		13:30 16:35 4h5m
1 Transfer
-----S- (Oct 4, Oct 11)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
13:40 16:50 4h10m
1 Transfer
-----S- (Oct 18)
13:30 16:35 4h5m
1 Transfer
-----S- (Oct 25)
WN446
Southwest Airlines 		13:45 18:35 5h50m
1 Transfer
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3714
Southwest Airlines 		15:00 16:45 2h45m
---TF-- (Oct 2–3)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
15:40 17:25 2h45m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-8-MAX
14:00 15:45 2h45m
------S (Oct 5, Oct 12, Oct 19, Oct 26)
737-8-MAX
15:00 16:45 2h45m
M--TF-- (Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24)
737-700 (WL)
14:50 16:35 2h45m
----F-- (Oct 31)
737-700 (WL)
WN301
Southwest Airlines 		14:45 19:15 5h30m
1 Transfer
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1345
Southwest Airlines 		14:55 16:40 2h45m
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1500
Southwest Airlines 		15:00 16:45 2h45m
--W---- (Oct 1)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1673
Southwest Airlines 		15:45 17:35 2h50m
------S (Oct 5, Oct 12, Oct 19, Oct 26)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2012
Southwest Airlines 		16:00 19:30 4h30m
1 Transfer
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3715
Southwest Airlines 		17:30 19:20 2h50m
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
18:10 19:55 2h45m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-800 (WL)
17:30 19:20 2h50m
M--TF-- (Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24)
737-8-MAX
17:50 19:35 2h45m
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
737-8-MAX
17:30 19:20 2h50m
M--T--- (Oct 27, Oct 30)
737-8-MAX
16:15 18:05 2h50m
----F-- (Oct 31)
737-800 (WL)
WN3675
Southwest Airlines 		16:15 19:25 4h10m
1 Transfer
------S (Oct 5, Oct 12, Oct 19, Oct 26)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN966
Southwest Airlines 		16:40 18:25 2h45m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3951
Southwest Airlines 		17:05 22:00 5h55m
1 Transfer
------S (Oct 5, Oct 12, Oct 19, Oct 26)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1961
Southwest Airlines 		17:20 21:45 5h25m
1 Transfer
------S (Oct 5, Oct 12, Oct 19, Oct 26)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2071
Southwest Airlines 		17:35 20:40 4h5m
1 Transfer
M--TF-- (Oct 2–3, Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2442
Southwest Airlines 		19:30 21:15 2h45m
---T--- (Oct 2)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
19:30 21:15 2h45m
----F-- (Oct 3)
737-8-MAX
19:15 21:00 2h45m
-----S- (Oct 4, Oct 11, Oct 18, Oct 25)
737-8-MAX
19:30 21:15 2h45m
M--TF-- (Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
737-8-MAX
19:25 21:10 2h45m
----F-- (Oct 31)
737-800 (WL)
WN748
Southwest Airlines 		19:55 21:40 2h45m
--W---- (Oct 1)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1488
Southwest Airlines 		20:50 22:35 2h45m
-TW---- (Oct 7–8, Oct 14–15, Oct 21–22, Oct 28–29)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1558
Southwest Airlines 		21:30 23:15 2h45m
---TF-- (Oct 2–3)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
21:25 23:10 2h45m
------S (Oct 5)
737-700 (WL)
21:25 23:10 2h45m
------S (Oct 12, Oct 19, Oct 26)
737-8-MAX
WN3620
Southwest Airlines 		21:40 23:25 2h45m
M--TF-- (Oct 6, Oct 9–10, Oct 13, Oct 16–17, Oct 20, Oct 23–24, Oct 27, Oct 30)
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 October 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.