Orlando (MCO) to Chicago (MDW) flights
2 airlines fly nonstop from Orlando (MCO) to Chicago (MDW): Frontier Airlines and Southwest Airlines. The two airports are 991 miles (1,595 km) apart. There are also 48 ways to fly it with one stop, through Indianapolis, Louisville and Knoxville and more.
Airlines flying nonstop from MCO to MDW
- Frontier AirlinesNot in an allianceWho books it
- Southwest AirlinesNot in an allianceWho books it
MCO to MDW with one stop
48 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Louisville (SDF)Southwest Airlines the whole way
- Via Knoxville (TYS)Allegiant Air the whole way
- Via Atlanta (ATL)Delta Air Lines, Frontier Airlines and 1 more the whole way
- Via Cincinnati (CVG)Southwest Airlines the whole way+1
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Birmingham (BHM)Southwest Airlines the whole way
- Via Charlotte (CLT)American Airlines and Frontier Airlines, then Southwest Airlines
- Via Charleston (CHS)Breeze Airways, then Southwest Airlines
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Myrtle Beach (MYR)Breeze Airways, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Sarasota (SRQ)Southwest Airlines the whole way
- Via Milwaukee (MKE)Southwest Airlines the whole way+1
- Via Grand Rapids (GRR)Southwest Airlines the whole way
MCO to MDW: common questions
Which airlines fly nonstop from MCO to MDW?
Frontier Airlines and Southwest Airlines fly nonstop from Orlando (MCO) to Chicago (MDW).
How far is Orlando from Chicago by plane?
Orlando (MCO) and Chicago (MDW) are 991 miles (1,595 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does MCO to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MCO to MDW with taxes and fees.
Where can I connect between Orlando and Chicago?
The most direct connections are through Indianapolis (IND), Louisville (SDF), Knoxville (TYS), Atlanta (ATL) and Cincinnati (CVG). On 44 of them the same airline flies both flights, for example Southwest Airlines through Indianapolis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.