Chicago (MDW) to Pensacola (PNS) flights
One airline flies nonstop from Chicago (MDW) to Pensacola (PNS): Southwest Airlines. The two airports are 782 miles (1,259 km) apart. There are also 18 ways to fly it with one stop, through Nashville, Memphis and Saint Louis and more.
Airlines flying nonstop from MDW to PNS
- Southwest AirlinesNot in an allianceWho books it
MDW to PNS with one stop
18 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)Southwest Airlines, then Breeze Airways
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Atlanta (ATL)Delta Air Lines the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Charlotte (CLT)Southwest Airlines, then American Airlines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Raleigh/Durham (RDU)Southwest Airlines, then Breeze Airways
- Via Tampa (TPA)Southwest Airlines, then Breeze Airways
- Via Orlando (MCO)Southwest Airlines and Frontier Airlines the whole way
- Via Dallas (DAL)Southwest Airlines the whole way
- Via Dallas (DFW)Frontier Airlines, then American Airlines
- Via Washington (DCA)Southwest Airlines, then American Airlines
- Via Houston (HOU)Southwest Airlines the whole way
- Via Austin (AUS)Southwest Airlines the whole way
MDW to PNS: common questions
Which airlines fly nonstop from MDW to PNS?
Southwest Airlines flies nonstop from Chicago (MDW) to Pensacola (PNS).
How far is Chicago from Pensacola by plane?
Chicago (MDW) and Pensacola (PNS) 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 MDW to PNS 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 PNS with taxes and fees.
Where can I connect between Chicago and Pensacola?
The most direct connections are through Nashville (BNA), Memphis (MEM), Saint Louis (STL), Atlanta (ATL) and Detroit (DTW). On 9 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.