Flights Orlando to Chicago MCO to MDW

Flights from Orlando (MCO) to Chicago (MDW): 3 airlines operate 137 flight numbers on this route, about 24 flights a week, distance 1595 km / 991 miles. The next departure is WN2802 (Southwest Airlines) on Sat, Nov 14 at 07:25 EST (12:25 GMT).

Airlines and flight numbers count operating flights from a year ago to a year ahead; code-share numbers are not counted. On time means landed less than 15 minutes late.

MCO Orlando Orlando International Airport MDW Chicago Chicago Midway International Airport
Route map MCO to MDW Great-circle route from Orlando International Airport, United States to Chicago Midway International Airport, United States, 1595 km. Map data: Natural Earth. UNITED STATES MCO MDW Map data: Natural Earth

Orlando to Chicago Flights

The 30 most recent of 137 flight numbers from MCO to MDW, with the date each last flew. Local times: MCO EST, MDW CST.

Flight Airline Last seen Departure Arrival
WN1597 Southwest Airlines Nov 14, 2026 11:20 13:15
WN2803 Southwest Airlines Nov 14, 2026 09:30 11:30
WN2802 Southwest Airlines Nov 14, 2026 07:25 09:20
WN2595 Southwest Airlines Nov 13, 2026 21:05 23:00
WN2806 Southwest Airlines Nov 13, 2026 18:40 20:35
WN2805 Southwest Airlines Nov 13, 2026 17:00 18:55
WN1109 Southwest Airlines Nov 13, 2026 16:00 18:00
WN2804 Southwest Airlines Nov 13, 2026 12:00 13:55
WN1731 Southwest Airlines Nov 11, 2026 16:10 18:05
WN152 Southwest Airlines Nov 8, 2026 07:10 09:10
WN2230 Southwest Airlines Nov 7, 2026 15:15 17:15
WN4135 Southwest Airlines Nov 6, 2026 07:45 09:40
WN4015 Southwest Airlines Nov 1, 2026 08:30 10:25
WN3351 Southwest Airlines Oct 31, 2026 16:25 18:15
WN1817 Southwest Airlines Oct 31, 2026 13:40 15:30
WN2853 Southwest Airlines Oct 31, 2026 12:30 14:20
WN1813 Southwest Airlines Oct 31, 2026 11:15 13:05
WN1810 Southwest Airlines Oct 31, 2026 08:40 10:30
WN2825 Southwest Airlines Oct 31, 2026 07:30 09:20
WN693 Southwest Airlines Oct 30, 2026 22:35 00:25
WN2909 Southwest Airlines Oct 30, 2026 19:50 21:40
WN1670 Southwest Airlines Oct 30, 2026 18:30 20:20
WN2490 Southwest Airlines Oct 30, 2026 14:25 16:15
WN1568 Southwest Airlines Oct 30, 2026 10:40 12:30
WN2152 Southwest Airlines Oct 30, 2026 08:10 10:00
WN2742 Southwest Airlines Oct 30, 2026 06:55 08:45
WN5014 Southwest Airlines Oct 29, 2026 11:55 13:45
WN2746 Southwest Airlines Oct 28, 2026 16:45 18:35
WN4077 Southwest Airlines Oct 28, 2026 12:50 14:40
WN2163 Southwest Airlines Oct 28, 2026 11:05 12:55

Upcoming flights

Local times at the departure airport.
Flight From To Scheduled Time Departure Status Details
WN2802 Orlando MCO Chicago MDW 07:25 Scheduled Track >
WN2803 Orlando MCO Chicago MDW 09:30 Scheduled Track >
WN1597 Orlando MCO Chicago MDW 11:20 11:40 Cancelled Track >

Recent flights

Local times at the departure airport.
Flight From To Date Scheduled Time Departure Status Details
WN2595 Orlando MCO Chicago MDW Nov 13 21:05 00:50 Unknown Track >
WN2806 Orlando MCO Chicago MDW Nov 13 18:40 01:27 Cancelled Track >
WN2805 Orlando MCO Chicago MDW Nov 13 17:00 22:00 Unknown Track >
WN1109 Orlando MCO Chicago MDW Nov 13 16:00 19:15 Cancelled Track >
WN2804 Orlando MCO Chicago MDW Nov 13 12:00 12:28 Landed Track >
WN2803 Orlando MCO Chicago MDW Nov 13 09:50 09:55 Landed Track >
WN2595 Orlando MCO Chicago MDW Nov 12 21:05 21:45 Landed Track >
WN2806 Orlando MCO Chicago MDW Nov 12 18:40 18:55 Landed Track >
WN2805 Orlando MCO Chicago MDW Nov 12 17:00 17:42 Landed Track >
WN1109 Orlando MCO Chicago MDW Nov 12 16:00 16:28 Landed Track >
WN2804 Orlando MCO Chicago MDW Nov 12 12:00 12:42 Landed Track >
WN2803 Orlando MCO Chicago MDW Nov 12 09:50 10:14 Landed Track >
WN2595 Orlando MCO Chicago MDW Nov 11 19:20 19:51 Landed Track >
WN2806 Orlando MCO Chicago MDW Nov 11 17:40 17:59 Landed Track >
WN1731 Orlando MCO Chicago MDW Nov 11 16:10 16:46 Landed Track >

Airlines flying MCO to MDW

MCO to MDW FAQ

How long is the flight from Orlando to Chicago?
About 2 h 25 min: that is the median flight time of the last 11 flights that landed; the timetable allows 2 h 55 min.
Which airlines fly from Orlando to Chicago?
Southwest Airlines, Frontier Airlines and Volaris have flights from Orlando (MCO) to Chicago (MDW) between a year ago and a year ahead. An airline listed may not fly the route every day.
How many flights a week go from Orlando to Chicago?
About 24 flights a week, counted over the two weeks before and after today. Only operating flights are counted, not code-share numbers.
Are flights from Orlando to Chicago on time?
11 of the last 11 flights that landed arrived less than 15 minutes after their scheduled time.
How far is Orlando from Chicago?
1595 km (991 miles) in a straight line between Orlando International Airport and Chicago Midway International Airport.

Chicago (MDW) to Orlando (MCO) flights >