Jacksonville (JAX) to Chicago (MDW) flights
One airline flies nonstop from Jacksonville (JAX) to Chicago (MDW): Southwest Airlines. The two airports are 850 miles (1,368 km) apart. There are also 27 ways to fly it with one stop, through Indianapolis, Knoxville and Atlanta and more.
Airlines flying nonstop from JAX to MDW
- Southwest AirlinesNot in an allianceWho books it
JAX to MDW with one stop
27 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Indianapolis (IND)Allegiant Air, then Southwest Airlines
- Via Knoxville (TYS)Allegiant Air the whole way
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
- Via Cincinnati (CVG)Allegiant Air, then Southwest Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Columbus (CMH)Breeze Airways, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Grand Rapids (GRR)Allegiant Air, then Southwest Airlines
- Via Raleigh/Durham (RDU)Breeze Airways, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Pittsburgh (PIT)Allegiant Air and Breeze Airways, then Southwest Airlines
- Via Richmond (RIC)Breeze Airways, then Southwest Airlines
- Via Washington (DCA)American Airlines, then Southwest Airlines
- Via Norfolk (ORF)Breeze Airways, then Southwest Airlines
JAX to MDW: common questions
Which airlines fly nonstop from JAX to MDW?
Southwest Airlines flies nonstop from Jacksonville (JAX) to Chicago (MDW).
How far is Jacksonville from Chicago by plane?
Jacksonville (JAX) and Chicago (MDW) are 850 miles (1,368 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does JAX 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 JAX to MDW with taxes and fees.
Where can I connect between Jacksonville and Chicago?
The most direct connections are through Indianapolis (IND), Knoxville (TYS), Atlanta (ATL), Cincinnati (CVG) and Nashville (BNA). On 10 of them the same airline flies both flights, for example Allegiant Air through Knoxville.
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.