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

August 2025
  • 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
WN147
Southwest Airlines 		07:15 09:00 2h45m
-----S- (Aug 9, Aug 16, Aug 23, Aug 30)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
06:50 08:35 2h45m
------S (Aug 10, Aug 17, Aug 24)
737-800 (WL)
06:20 08:05 2h45m
------S (Aug 31)
737-700 (WL)
WN1053
Southwest Airlines 		06:20 08:05 2h45m
M--TF-- (Aug 7–8, Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
F93853
Frontier Airlines 		18:23 20:22 2h59m
---T-S- (Aug 2, Aug 7, Aug 9, Aug 14, Aug 16)
A320neo Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
13:10 15:06 2h56m
M---F-S (Aug 4, Aug 8, Aug 10–11, Aug 15, Aug 17–18)
A320neo
06:30 08:22 2h52m
----F-S (Aug 22, Aug 24, Aug 29, Aug 31)
A320neo
08:00 09:54 2h54m
-----S- (Aug 23, Aug 30)
A320neo
13:33 15:29 2h56m
M------ (Aug 25)
A320neo
Codeshare flight ▼
WN3716
Southwest Airlines 		06:35 08:20 2h45m
M------ (Aug 4)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3591
Southwest Airlines 		07:10 08:55 2h45m
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
10:30 12:15 2h45m
---TF-- (Aug 7–8)
737-700 (WL)
09:50 11:30 2h40m
-----S- (Aug 9, Aug 16)
737-700 (WL)
10:30 12:15 2h45m
M--TF-- (Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
737-700 (WL)
10:10 11:55 2h45m
-----S- (Aug 23, Aug 30)
737-700 (WL)
WN836
Southwest Airlines 		07:15 10:35 4h20m
1 Transfer
M--TF-- (Aug 7–8, Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1570
Southwest Airlines 		07:35 09:20 2h45m
M--TF-- (Aug 7–8, Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1719
Southwest Airlines 		07:55 09:45 2h50m
M------ (Aug 4)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2131
Southwest Airlines 		08:00 11:00 4h0m
1 Transfer
M------ (Aug 4)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2288
Southwest Airlines 		08:15 10:00 2h45m
------S (Aug 31)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN4077
Southwest Airlines 		09:40 12:50 4h10m
1 Transfer
---TF-- (Aug 7–8)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
08:55 12:10 4h15m
1 Transfer
------S (Aug 10, Aug 17, Aug 24)
09:40 12:50 4h10m
1 Transfer
M--TF-- (Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
WN1565
Southwest Airlines 		09:00 12:05 4h5m
1 Transfer
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1537
Southwest Airlines 		09:10 12:50 4h40m
1 Transfer
------S (Aug 31)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1488
Southwest Airlines 		09:15 13:50 5h35m
1 Transfer
------S (Aug 10, Aug 17, Aug 24)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3255
Southwest Airlines 		09:20 11:05 2h45m
M------ (Aug 4)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3546
Southwest Airlines 		09:25 14:40 6h15m
2 Transfers
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN951
Southwest Airlines 		09:50 13:55 5h5m
1 Transfer
M--TF-- (Aug 7–8, Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1373
Southwest Airlines 		10:05 11:50 2h45m
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
12:20 14:05 2h45m
---TF-- (Aug 7–8)
737-800 (WL)
12:10 13:50 2h40m
-----S- (Aug 9, Aug 16, Aug 23, Aug 30)
737-800 (WL)
10:05 11:50 2h45m
------S (Aug 10, Aug 17, Aug 24)
737-8-MAX
12:20 14:05 2h45m
M--TF-- (Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
737-800 (WL)
WN367
Southwest Airlines 		10:05 14:10 5h5m
1 Transfer
M------ (Aug 4)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1104
Southwest Airlines 		10:40 14:45 5h5m
1 Transfer
M--TF-- (Aug 7–8, Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3870
Southwest Airlines 		11:25 13:05 2h40m
------S (Aug 10, Aug 17, Aug 24)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2549
Southwest Airlines 		11:25 13:10 2h45m
M------ (Aug 4)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2409
Southwest Airlines 		11:45 13:25 2h40m
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1687
Southwest Airlines 		11:50 15:35 4h45m
1 Transfer
-----S- (Aug 9, Aug 16, Aug 23, Aug 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1766
Southwest Airlines 		12:00 15:10 4h10m
1 Transfer
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN818
Southwest Airlines 		12:00 16:25 5h25m
1 Transfer
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1140
Southwest Airlines 		12:35 14:20 2h45m
------S (Aug 31)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2303
Southwest Airlines 		14:25 19:00 5h35m
1 Transfer
-----S- (Aug 9, Aug 16, Aug 23, Aug 30)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1500
Southwest Airlines 		15:00 16:45 2h45m
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN935
Southwest Airlines 		15:30 17:15 2h45m
------S (Aug 10, Aug 17, Aug 24)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1788
Southwest Airlines 		15:30 17:25 2h55m
M------ (Aug 4)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1186
Southwest Airlines 		15:35 17:20 2h45m
-----S- (Aug 9, Aug 16, Aug 23, Aug 30)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1765
Southwest Airlines 		15:50 19:20 4h30m
1 Transfer
M------ (Aug 4)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN1972
Southwest Airlines 		16:25 18:15 2h50m
---TF-- (Aug 7–8)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
17:00 18:50 2h50m
-----S- (Aug 9, Aug 16, Aug 23, Aug 30)
737-700 (WL)
18:20 20:10 2h50m
------S (Aug 10, Aug 17, Aug 24)
737-800 (WL)
16:25 18:15 2h50m
M--TF-- (Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
737-700 (WL)
17:10 19:00 2h50m
------S (Aug 31)
737-8-MAX
WN3595
Southwest Airlines 		16:35 18:25 2h50m
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
737-8-MAX Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
17:40 19:25 2h45m
M--TF-- (Aug 7–8, Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
737-800 (WL)
WN2909
Southwest Airlines 		16:50 19:50 4h0m
1 Transfer
------S (Aug 10, Aug 17, Aug 24)
Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3724
Southwest Airlines 		17:45 19:45 3h0m
M------ (Aug 4)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN748
Southwest Airlines 		19:55 21:40 2h45m
-TW---- (Aug 5–6, Aug 12–13, Aug 19–20, Aug 26–27)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
20:40 22:25 2h45m
---TF-- (Aug 7–8)
737-800 (WL)
18:30 20:20 2h50m
-----S- (Aug 9, Aug 16, Aug 23, Aug 30)
737-700 (WL)
19:40 21:25 2h45m
------S (Aug 10, Aug 17, Aug 24)
737-800 (WL)
20:40 22:25 2h45m
M--TF-- (Aug 11, Aug 14–15, Aug 18, Aug 21–22, Aug 25, Aug 28–29)
737-800 (WL)
19:15 21:00 2h45m
------S (Aug 31)
737-800 (WL)
WN3726
Southwest Airlines 		20:15 22:05 2h50m
M------ (Aug 4)
737-800 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN2634
Southwest Airlines 		21:50 23:40 2h50m
M------ (Aug 4)
737-700 (WL) Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
WN3277
Southwest Airlines 		22:10 23:55 2h45m
------S (Aug 10, Aug 17, Aug 24)
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 August 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.