Charleston (CHS) to Chicago (MDW) flights
One airline flies nonstop from Charleston (CHS) to Chicago (MDW): Southwest Airlines. The two airports are 746 miles (1,201 km) apart. There are also 28 ways to fly it with one stop, through Cincinnati, Charlotte and Louisville and more.
Airlines flying nonstop from CHS to MDW
- Southwest AirlinesNot in an allianceWho books it
CHS to MDW with one stop
28 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Cincinnati (CVG)Allegiant Air and Breeze Airways, then Southwest Airlines
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Louisville (SDF)Breeze Airways, then Southwest Airlines
- Via Columbus (CMH)Breeze Airways, then Southwest Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Atlanta (ATL)Delta Air Lines the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Pittsburgh (PIT)Breeze Airways, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Richmond (RIC)Breeze Airways, then Southwest Airlines
- Via Washington (DCA)American Airlines, then Southwest Airlines
- Via Norfolk (ORF)Breeze Airways, then Southwest Airlines
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Philadelphia (PHL)American Airlines, then Southwest Airlines
- Via Rochester (ROC)Breeze Airways, then Southwest Airlines
CHS to MDW: common questions
Which airlines fly nonstop from CHS to MDW?
Southwest Airlines flies nonstop from Charleston (CHS) to Chicago (MDW).
How far is Charleston from Chicago by plane?
Charleston (CHS) and Chicago (MDW) are 746 miles (1,201 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does CHS 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 CHS to MDW with taxes and fees.
Where can I connect between Charleston and Chicago?
The most direct connections are through Cincinnati (CVG), Charlotte (CLT), Louisville (SDF), Columbus (CMH) and Nashville (BNA). On 6 of them the same airline flies both flights, for example Southwest Airlines through Nashville.
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.