Chicago (MDW) to Fort Myers (RSW) flights
One airline flies nonstop from Chicago (MDW) to Fort Myers (RSW): Southwest Airlines. The two airports are 1,108 miles (1,783 km) apart. There are also 38 ways to fly it with one stop, through Atlanta, Louisville and Indianapolis and more.
Airlines flying nonstop from MDW to RSW
- Southwest AirlinesNot in an allianceWho books it
MDW to RSW with one stop
38 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Atlanta (ATL)Delta Air Lines the whole way
- Via Louisville (SDF)Southwest Airlines the whole way
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Orlando (MCO)Southwest Airlines the whole way
- Via Cincinnati (CVG)Southwest Airlines, then Delta Air Lines and Frontier Airlines
- Via Charlotte (CLT)Southwest Airlines, then American Airlines
- Via Charleston (CHS)Southwest Airlines, then Breeze Airways
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Grand Rapids (GRR)Southwest Airlines the whole way
- Via Raleigh/Durham (RDU)Southwest Airlines, then Delta Air Lines and Breeze Airways
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Cleveland (CLE)Southwest Airlines the whole way
MDW to RSW: common questions
Which airlines fly nonstop from MDW to RSW?
Southwest Airlines flies nonstop from Chicago (MDW) to Fort Myers (RSW).
How far is Chicago from Fort Myers by plane?
Chicago (MDW) and Fort Myers (RSW) are 1,108 miles (1,783 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does MDW to RSW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to RSW with taxes and fees.
Where can I connect between Chicago and Fort Myers?
The most direct connections are through Atlanta (ATL), Louisville (SDF), Indianapolis (IND), Nashville (BNA) and Orlando (MCO). On 25 of them the same airline flies both flights, for example Delta Air Lines through Atlanta.
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.