Flights from Chicago to Orlando – Direct & connecting routes
Non-stop airlines Connecting flights Show map Price search
MDW to MCO – All flight route options from Chicago Midway International, Illinois, USA to Orlando International, Florida, USA. These routes are operated by 3 airlines. Fly non-stop with Southwest Airlines or Frontier Airlines, or choose from 28 different stopover flights. The shortest flight time is 2 hours and 35 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.
Find the best prices on hotels and car rental near Orlando
We got great deals on hotels and car rentals near the airport.
Chicago to Orlando flights
There are over 25 airlines and as many as 205 flights every week to this destination. You can fly non-stop to Orlando (MCO) from Chicago (MDW) with Southwest Airlines or Frontier Airlines but if a stopover option suits you better you can choose to fly via Birmingham, Columbus or any other of the 23 alternatives with connectiing airports.
Chicago to Orlando with Southwest Airlines
You can fly non-stop every weekday with flights departing from 5:00 am to 9:00 pm. You can also catch a transit flight via Birmingham or Columbus.
With Delta Air Lines
If you fly to Orlando from Chicago with Delta Air Lines you will do a stopover in Atlanta. Delta Air Lines is a member of SkyTeam.
Distance & flight times: Midway International Airport to Orlando International
The shortest flight time between MDW and MCO is 2 hours and 40 minutes.
Via | Total flight time | Layover time | Distance |
---|---|---|---|
Direct | 2h 40m | - | 996 miles (1603 km) |
BHM Birmingham | 4h 20m | 1h 5m | 1054 miles (1696 km) |
CMH Columbus | 4h 35m | 2h 5m | 1092 miles (1757 km) |
STL Saint Louis | 4h 45m | 2h 10m | 1138 miles (1831 km) |
CLE Cleveland | 4h 55m | 45m | 1209 miles (1945 km) |
FLL Fort Lauderdale | 5h 0m | 45m | 1354 miles (2179 km) |
ATL Atlanta | 5h 6m | 1h 24m | 1000 miles (1609 km) |
BNA Nashville | 5h 15m | 1h 40m | 1017 miles (1636 km) |
PIT Pittsburgh | 5h 28m | 1h 20m | 1243 miles (2000 km) |
ORF Norfolk | 5h 33m | 1h 55m | 1365 miles (2196 km) |
DCA Washington | 5h 33m | 1h 15m | 1367 miles (2200 km) |
SDF Louisville | 5h 35m | 1h 35m | 995 miles (1601 km) |
MEM Memphis | 5h 43m | 1h 40m | 1169 miles (1881 km) |
BUF Buffalo | 5h 45m | 1h 40m | 1487 miles (2393 km) |
MCI Kansas City | 5h 45m | 55m | 1484 miles (2388 km) |
RDU Raleigh/Durham | 5h 48m | 2h 50m | 1173 miles (1887 km) |
MSP Minneapolis | 5h 49m | 2h 33m | 1668 miles (2684 km) |
MSY New Orleans | 5h 55m | 1h 45m | 1383 miles (2225 km) |
PHL Philadelphia | 6h 6m | 1h 13m | 1537 miles (2473 km) |
DTW Detroit | 6h 12m | 2h 1m | 1193 miles (1920 km) |
TUL Tulsa | 6h 40m | - | - |
OMA Omaha | 6h 45m | 1h 10m | 1641 miles (2640 km) |
BWI Baltimore | 7h 10m | 2h 15m | 1405 miles (2261 km) |
GRR Grand Rapids | 7h 15m | 1h 35m | 1168 miles (1879 km) |

