Fort Myers (RSW) to Chicago (MDW) flights
One airline flies nonstop from Fort Myers (RSW) to Chicago (MDW): 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 RSW to MDW
- Southwest AirlinesNot in an allianceWho books it
RSW to MDW 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)Delta Air Lines and Frontier Airlines, then Southwest Airlines
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Charleston (CHS)Breeze Airways, then Southwest Airlines
- 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)Delta Air Lines and Breeze Airways, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Cleveland (CLE)Southwest Airlines the whole way
RSW to MDW: common questions
Which airlines fly nonstop from RSW to MDW?
Southwest Airlines flies nonstop from Fort Myers (RSW) to Chicago (MDW).
How far is Fort Myers from Chicago by plane?
Fort Myers (RSW) and Chicago (MDW) 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 RSW 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 RSW to MDW with taxes and fees.
Where can I connect between Fort Myers and Chicago?
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.