Pensacola (PNS) to Chicago (MDW) flights
One airline flies nonstop from Pensacola (PNS) to Chicago (MDW): Southwest Airlines. The two airports are 782 miles (1,259 km) apart. There are also 17 ways to fly it with one stop, through Nashville, Memphis and Saint Louis and more.
Airlines flying nonstop from PNS to MDW
- Southwest AirlinesNot in an allianceWho books it
PNS to MDW with one stop
17 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Memphis (MEM)Breeze Airways, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Atlanta (ATL)Delta Air Lines the whole way
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Raleigh/Durham (RDU)Breeze Airways, then Southwest Airlines
- Via Tampa (TPA)Breeze Airways, then Southwest Airlines
- Via Orlando (MCO)Frontier Airlines and Southwest Airlines the whole way
- Via Dallas (DAL)Southwest Airlines the whole way
- Via Dallas (DFW)American Airlines, then Frontier Airlines
- Via Washington (DCA)American Airlines, then Southwest Airlines
- Via Houston (HOU)Southwest Airlines the whole way
- Via Austin (AUS)Southwest Airlines the whole way
- Via Philadelphia (PHL)American Airlines, then Southwest Airlines
PNS to MDW: common questions
Which airlines fly nonstop from PNS to MDW?
Southwest Airlines flies nonstop from Pensacola (PNS) to Chicago (MDW).
How far is Pensacola from Chicago by plane?
Pensacola (PNS) and Chicago (MDW) are 782 miles (1,259 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does PNS 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 PNS to MDW with taxes and fees.
Where can I connect between Pensacola and Chicago?
The most direct connections are through Nashville (BNA), Memphis (MEM), Saint Louis (STL), Atlanta (ATL) and Charlotte (CLT). On 8 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.