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Direct flights from Chicago to Pensacola

Did you mean Flights from Pensacola to Chicago?

Flightmap/Flights from MDW/MDW to PNS

Chicago

United States

MDW

Chicago Midway International Airport

Pensacola

United States

PNS

Pensacola Regional Airport

Route
Nonstop service available
Distance
782 miles
Marketing airlines
1 airline
Aircraft
3 aircraft types
Dates
Nov 21, 2026 – Aug 2, 2027

Observed award fares

A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.

Departure window: 2026-10-23 – 2026-11-21.

No recent fares appear in this limited preview. This does not mean the route is sold out. Use the search controls to check other dates and routes.

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Explore these airports and cities

  • Flights from MDW
  • Flights to PNS
  • Award flights to Chicago

Chicago to Pensacola route overview

Chicago Midway International Airport (MDW) serves Chicago; Pensacola Regional Airport (PNS) serves Pensacola.

The airports are 782 miles apart by great-circle distance.

Roame's current schedule feed shows nonstop service from MDW to PNS.

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Published schedule dates span Nov 21, 2026 – Aug 2, 2027.

Marketing airlines on the Chicago to Pensacola route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

Aircraft flying from MDW to PNS

Frequently asked questions

Which airports serve the Chicago to Pensacola route?

Chicago Midway International Airport (MDW) is the origin airport and Pensacola Regional Airport (PNS) is the destination airport.

How far is Pensacola from Chicago?

MDW and PNS are approximately 782 miles apart by great-circle distance.

Are there direct flights from MDW to PNS?

Yes. Roame's current schedule feed shows nonstop service from MDW to PNS.

Which airlines market flights from MDW to PNS?

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Which aircraft fly from MDW to PNS?

Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H), Boeing 737 MAX 8 (7M8) and 7S7.

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