Cleveland (CLE) to Chicago (MDW) flights
One airline flies nonstop from Cleveland (CLE) to Chicago (MDW): Southwest Airlines. The two airports are 306 miles (493 km) apart. There are also 11 ways to fly it with one stop, through Detroit, Saint Louis and Nashville and more.
Airlines flying nonstop from CLE to MDW
- Southwest AirlinesNot in an allianceWho books it
CLE to MDW with one stop
11 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Washington (DCA)American Airlines, then Southwest Airlines
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Philadelphia (PHL)American Airlines, then Southwest Airlines
- Via Raleigh/Durham (RDU)Frontier Airlines, then Southwest Airlines
- Via New York (LGA)American Airlines and Delta Air Lines, then Southwest Airlines
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
CLE to MDW: common questions
Which airlines fly nonstop from CLE to MDW?
Southwest Airlines flies nonstop from Cleveland (CLE) to Chicago (MDW).
How far is Cleveland from Chicago by plane?
Cleveland (CLE) and Chicago (MDW) are 306 miles (493 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does CLE 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 CLE to MDW with taxes and fees.
Where can I connect between Cleveland and Chicago?
The most direct connections are through Detroit (DTW), Saint Louis (STL), Nashville (BNA), Washington (DCA) and Baltimore (BWI). On 6 of them the same airline flies both flights, for example Delta Air Lines through Detroit.
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.