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

MDW Airport Page →
782 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 20 1-stop flights Verified 1mo ago
Also flown by charter / private operators: NetJets Aviation, Aerolink Uganda.
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 35m EJAWN → WN Nashville (BNA) to Pensacola flights
STL St Louis 3h 45m WN → WN St Louis (STL) to Pensacola flights
ATL Atlanta 3h 46m AFAMDL → AFAMDL Atlanta (ATL) to Pensacola flights
CLT Charlotte 4h 24m LXJWN → AA Charlotte (CLT) to Pensacola flights
MCO Orlando 4h 59m WN → F9Y4 Orlando (MCO) to Pensacola flights
DAL Dallas 5h 3m EJAWN → WN Dallas (DAL) to Pensacola flights
HOU Houston 5h 7m WN → WN Houston (HOU) to Pensacola flights
DCA Washington 5h 12m WN → AAAS Washington (DCA) to Pensacola flights
DFW Dallas-Fort Worth 5h 19m F9Y4 → AAASAY Dallas-Fort Worth (DFW) to Pensacola flights
AUS Austin 5h 20m LXJWN → WN Austin (AUS) to Pensacola flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Pensacola
Connecting service available through multiple hubs.
1 Airlines 782 mi 2h 10m nonstop

MDW–PNS 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 10m.

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

Airline Landscape

Carriers that operated nonstop MDW–PNS service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 0 – – 70% – –
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 MDW to PNS.
1-STOP
One-Stop Connections
20
Hubs
~3h
Fastest
~16h
Longest
BNA ~3h 35m STL ~3h 45m ATL ~3h 46m MEM ~4h 24m CLT ~4h 24m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,268
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
MDW → PNS
70%
Moderate delays possible. Allow buffer time.
Departing
70%
Arriving
80%
Return
PNS → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
75%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays → PNS delays →
Alternatives

Other ways to reach Pensacola from Chicago

Nearby airports with service to Pensacola International Airport.
Metric MDW→PNS ORD→PNS
Distance from MDW – 15 mi
Nonstop airlines – 3
Weekly flights – 21
Flight time 2h 10m 2h 23m
Departure OTP 70% –
Chicago (ORD) to Pensacola flights
Airports within 200 miles of MDW with service to Pensacola International Airport.
Know before you go

Travel Essentials

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

When it's 6:00 PM in Chicago, it's 6:00 PM in Pensacola.
Distance & Flight Time
782 mi / 1,259 km
Nonstop flight time is approximately 2h 10m gate to gate.
Facts

MDW–PNS Quick Facts

Key statistics for the Chicago to Pensacola route.
Route details
Distance782 mi / 1,259 km
Flight time2h 10m
Time difference0 hours
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: PNS
Full namePensacola International Airport
IATA / ICAOPNS / KPNS
TimezoneAmerica/Chicago
Passengers/yr3.1M
Elevation121 ft / 37 m
FAQ

Frequently Asked Questions

Common questions about MDW to PNS flights.
Nonstop flights from Chicago Midway International Airport to Pensacola International Airport take about 2h 10m gate to gate. The route covers 782 miles.
1 airline operated the nonstop from MDW to PNS: 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 10m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Nashville, St. Louis Lambert and Hartsfield Jackson Atlanta.
On a single ticket, yes. Your bags are checked through to PNS 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 PNS to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ORD. 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 MDW to PNS

Chicago Midway International Airport (MDW) and Pensacola International Airport (PNS) 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.

MDW to PNS Flight Duration and Schedule

Nonstop flight time from MDW to PNS is about 2 hours 10 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, St. Louis Lambert and Hartsfield Jackson Atlanta. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD).