Pensacola to Chicago (PNS–MDW) — Airlines, Schedules & Connections

PNS Airport Page →
782 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 21 1-stop flights Verified 1mo ago
Also flown by charter / private operators: NetJets Aviation.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

Last scheduled nonstop: Aug 2026.

✦ 1-Stop connections via 10 hubs
BNA Nashville 3h 45m WN → NJMWN Nashville (BNA) to Chicago flights
ATL Atlanta 3h 56m AFAMDL → AFAMDL Atlanta (ATL) to Chicago flights
STL St Louis 4h 3m WN → WN St Louis (STL) to Chicago flights
MCI Kansas City 4h 15m WN → WN Kansas City (MCI) to Chicago flights
DAL Dallas 4h 50m WN → WN Dallas (DAL) to Chicago flights
HOU Houston 4h 50m WN → WN Houston (HOU) to Chicago flights
TPA Tampa 4h 55m MX → NJEWN Tampa (TPA) to Chicago flights
AUS Austin 5h 15m WN → WN Austin (AUS) to Chicago flights
MCO Orlando 5h 17m F9MX → WN Orlando (MCO) to Chicago flights
PHL Philadelphia 5h 31m AAAS → WN Philadelphia (PHL) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Pensacola to Chicago
Connecting service available through multiple hubs.
1 Airlines 782 mi 2h 15m nonstop

PNS–MDW had nonstop service from Southwest Airlines, last on the schedule in August 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 782 miles in 2h 15m.

Also explore Browse available seat maps PNS Routes MDW Routes PNS Live Flights MDW Live Flights PNS Delays MDW Delays
All flights from Chicago (MDW) Chicago to Pensacola flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop PNS–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 0 – – 100% – –
Alliance coverage
Unaffiliated: WN (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for PNS to MDW.
1-STOP
One-Stop Connections
21
Hubs
~3h
Fastest
~16h
Longest
BNA ~3h 45m ATL ~3h 56m STL ~4h 3m MCI ~4h 15m MEM ~4h 34m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,261
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
PNS → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
54%
Return
MDW → PNS
72%
Moderate delays possible. Allow buffer time.
Departing
72%
Arriving
72%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. PNS delays → MDW delays →
Alternatives

Other ways to reach Chicago from Pensacola

Nearby airports with service to Chicago Midway International Airport.
Metric PNS→MDW VPS→MDW DSI→MDW
Distance from PNS – 40 mi 43 mi
Nonstop airlines – 1 1
Weekly flights – 4 –
Flight time 2h 15m 2h 18m 1h 59m
Departure OTP 100% – –
Valparaiso (VPS) to Chicago flights · Destin (DSI) to Chicago flights · Mobile (MOB) to Chicago flights
Airports within 200 miles of PNS with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
0h
Chicago is 0 hours the same as Pensacola.
PNS: CDT · MDW: CDT

When it's 6:00 PM in Pensacola, it's 6:00 PM in Chicago.
Distance & Flight Time
782 mi / 1,259 km
Nonstop flight time is approximately 2h 15m gate to gate.
Facts

PNS–MDW Quick Facts

Key statistics for the Pensacola to Chicago route.
Route details
Distance782 mi / 1,259 km
Flight time2h 15m
Time difference0 hours
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: PNS
Full namePensacola International Airport
IATA / ICAOPNS / KPNS
TimezoneAmerica/Chicago
Passengers/yr3.1M
Elevation121 ft / 37 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about PNS to MDW flights.
Nonstop flights from Pensacola International Airport to Chicago Midway International Airport take about 2h 15m gate to gate. The route covers 782 miles.
1 airline operated the nonstop from PNS to MDW: Southwest Airlines. The last scheduled nonstop was in August 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in August 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 2h 15m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Nashville, Hartsfield Jackson Atlanta and St. Louis Lambert.
On a single ticket, yes. Your bags are checked through to MDW and move between planes without you. On two separate tickets you collect your bags at the connecting airport and recheck them, so build in extra layover time.
Yes, return flights from MDW to PNS are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include VPS, DSI and MOB. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from PNS to MDW

Pensacola International Airport (PNS) and Chicago Midway International Airport (MDW) had nonstop service from Southwest Airlines, last on the schedule in August 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

PNS to MDW Flight Duration and Schedule

Nonstop flight time from PNS to MDW is about 2 hours 15 minutes gate to gate. The route covers a distance of 782 miles (1,259 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Nashville, Hartsfield Jackson Atlanta and St. Louis Lambert. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Valparaiso (VPS), Destin (DSI) and Mobile (MOB).