Cheap Flight Tickets from Pensacola (PNS) to Chicago (MDW), Starting at $384

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

$384

DL Delta Airlines • 1 stop • 10h 53m

Jul 08 – Jul 11

The cheapest round trip flight from Pensacola to Chicago (PNS-MDW-PNS) is currently $384

🔍 Search Flights

Cheapest Direct Flight

$511

WN Southwest Airlines • nonstop • 3h 35m

Jun 30

The cheapest nonstop flight from Pensacola to Chicago (PNS-MDW) is currently $511

🔍 Search Flights

Fastest Flight

3h 35m

The fastest nonstop flight from Pensacola to Chicago (PNS-MDW) takes 3h 35m

Top Airlines Flying from Pensacola to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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.

Jul 08 - Jul 11, Economy
DL
Pensacola → Chicago
10h 53m
9:22 AM - 4:15 PM • 1 stop
DL
Pensacola → Chicago
7h 30m
1:39 PM - 6:29 PM • 1 stop
$384
Delta Airlines
Jul 08 - Jul 11, Economy
WN
Pensacola → Chicago
5h 40m
5:30 PM - 9:10 PM • 1 stop
WN
Pensacola → Chicago
3h 30m
9:00 AM - 11:10 AM • nonstop
$553
Southwest Airlines
Jul 08 - Jul 11, Economy
WN
Pensacola → Chicago
10h
6:10 PM - 12:10 AM • 1 stop
WN
Pensacola → Chicago
10h 5m
2:35 PM - 8:40 PM • 1 stop
$562
Southwest Airlines
Jul 08 - Jul 11, Economy
WN
Pensacola → Chicago
9h 5m
5:30 PM - 11:15 PM • 1 stop
WN
Pensacola → Chicago
8h 20m
9:15 AM - 2:15 PM • 1 stop
$562
Southwest Airlines
Jul 08 - Jul 11, Economy
WN
Pensacola → Chicago
8h 20m
5:45 AM - 10:45 AM • 1 stop
WN
Pensacola → Chicago
10h 15m
8:00 AM - 2:15 PM • 2 stops
$568
Southwest Airlines
Jul 08 - Jul 11, Economy
WN
Pensacola → Chicago
5h 40m
5:30 PM - 9:10 PM • 1 stop
WN
Pensacola → Chicago
10h 15m
8:00 AM - 2:15 PM • 2 stops
$568
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?
Yes, you can fly PNS to MDW non-stop on
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 5:45 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 562
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 7:34 pm

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

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

More Flight Options for Pensacola (PNS) and Chicago (MDW)

Why Fareleaders for PNS to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Pensacola to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on PNS to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Pensacola to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Pensacola (PNS) to Chicago (MDW)
Terms and Conditions*