Cheap Flight Tickets from Pensacola (PNS) to Chicago (MDW), Starting at $433

Good to Know: Cheapest and Fastest PNS - MDW Flights

Useful information for finding best airline tickets from Pensacola Regional to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$439

WN Southwest Airlines • 2 stops • 20h 55m

Nov 06 – Nov 13

The cheapest round trip flight from Pensacola to Chicago (PNS-MDW-PNS) is currently $439

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Fastest Flight

7h 33m

The fastest nonstop flight from Pensacola to Chicago (PNS-MDW) takes 7h 33m

Latest Flight Deals from Pensacola (PNS) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Pensacola to Chicago. Ideal for travelers with confirmed return itineraries.

Nov 06 - Nov 13, Economy
WN
Pensacola → Chicago
20h 55m
5:55 PM - 6:50 AM • 2 stops
WN
Pensacola → Chicago
20h
5:20 AM - 5:20 PM • 1 stop
$439
Southwest Airlines
Nov 05 - Nov 12, Economy
WN
Pensacola → Chicago
21h 40m
5:55 PM - 6:55 AM • 2 stops
WN
Pensacola → Chicago
33h 20m
9:20 PM - 5:20 PM • 2 stops
$539
Southwest Airlines
Nov 05 - Nov 12, Economy
WN
Pensacola → Chicago
20h 25m
7:45 AM - 8:10 PM • 2 stops
WN
Pensacola → Chicago
33h 20m
9:20 PM - 5:20 PM • 2 stops
$539
Southwest Airlines
Nov 05 - Nov 12, Economy
WN
Pensacola → Chicago
18h 40m
5:25 AM - 4:45 PM • 1 stop
WN
Pensacola → Chicago
20h
5:20 AM - 5:20 PM • 1 stop
$583
Southwest Airlines
Nov 05 - Nov 12, Economy
WN
Pensacola → Chicago
22h 25m
10:25 AM - 12:10 AM • 2 stops
WN
Pensacola → Chicago
14h 10m
8:30 AM - 5:20 PM • 1 stop
$589
Southwest Airlines
Nov 06 - Nov 13, Economy
WN
Pensacola → Chicago
12h 15m
10:25 AM - 6:00 PM • 1 stop
WN
Pensacola → Chicago
12h 30m
12:45 PM - 8:35 PM • 2 stops
$612
Southwest Airlines

Fly from Pensacola to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Pensacola to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Pensacola to Chicago Flights

What are the airports in Pensacola?
PNS
What’s the most popular airline flying from PNS to MDW?
The most popular airline flying from Pensacola to Chicago are
Can I fly from PNS to MDW non-stop?
NO
Which airlines fly nonstop between Pensacola and Chicago?
The non-stop flights between Pensacola and Chicago are .
What’s the earliest departure time from PNS to MDW Airport?
The earliest flight leaves PNS at 5:25 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Pensacola to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from PNS to MDW?
Read the fare rules of the Pensacola to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Pensacola and Chicago?
operate flights between Pensacola and Chicago
How long does a flight from Pensacola to Chicago take?
It takes approximately 2 hour to fly non-stop from PNS to MDW, which is 780.63 miles by air.
Which airlines provide the cheapest flights from Pensacola (PNS) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from PNS were found on WN : USD 539
Do I need a passport to fly between PNS and MDW?
No
What’s the latest departure time from PNS to MDW ?
The last flight leaves PNS at 5:55 pm

Pensacola (PNS) to Chicago (MDW): Airport Information

Origin Airport Pensacola Regional , Pensacola, US
Destination Airport Chicago Midway International , Chicago, US
Distance 781 miles

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