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

Good to Know: Cheapest and Fastest MDW - PNS Flights

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

Cheapest Round Trip Flight

$384

DL Delta Airlines • 1 stop • 10h 15m

Jul 18 – Jul 29

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

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Cheapest Direct Flight

$607

WN Southwest Airlines • nonstop • 3h 35m

Jul 23

The cheapest nonstop flight from Chicago to Pensacola (MDW-PNS) is currently $607

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Fastest Flight

3h 35m

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

Top Airlines Flying from Chicago to Pensacola

Delta Airline, DL

Delta Airlines

Southwest Airlines-WN

Southwest Airlines

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

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

Jul 18 - Jul 29, Economy
DL
Chicago → Pensacola
10h 15m
10:55 AM - 5:10 PM • 1 stop
DL
Chicago → Pensacola
6h 45m
6:00 AM - 10:05 AM • 1 stop
$384
Delta Airlines
Jul 18 - Jul 29, Economy
DL
Chicago → Pensacola
10h 20m
4:22 PM - 10:42 PM • 1 stop
DL
Chicago → Pensacola
7h 13m
8:01 AM - 12:34 PM • 1 stop
$384
Delta Airlines
Jul 18 - Jul 29, Economy
DL
Chicago → Pensacola
7h 9m
4:22 PM - 8:51 PM • 1 stop
DL
Chicago → Pensacola
11h 54m
7:00 AM - 2:14 PM • 1 stop
$384
Delta Airlines
Jul 18 - Jul 29, Economy
DL
Chicago → Pensacola
10h 55m
6:00 AM - 12:55 PM • 1 stop
DL
Chicago → Pensacola
6h 55m
4:18 PM - 8:33 PM • 1 stop
$384
Delta Airlines
Jul 23 - Jul 25, Economy
WN
Chicago → Pensacola
15h 5m
7:15 AM - 4:20 PM • 1 stop
WN
Chicago → Pensacola
3h 35m
3:50 PM - 6:05 PM • nonstop
$617
Southwest Airlines
Jul 23 - Jul 25, Economy
WN
Chicago → Pensacola
5h 40m
1:00 PM - 4:40 PM • 1 stop
WN
Chicago → Pensacola
8h 30m
11:50 AM - 5:00 PM • 1 stop
$626
Southwest Airlines

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

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

FAQs on Chicago to Pensacola Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to PNS?
The most popular airline flying from Chicago to Pensacola are
Can I fly from MDW to PNS non-stop?
Yes, you can fly MDW to PNS non-stop on
Which airlines fly nonstop between Chicago and Pensacola?
The non-stop flights between Chicago and Pensacola are .
What’s the earliest departure time from MDW to PNS Airport?
The earliest flight leaves MDW at 6:00 am and lands in PNS - Pensacola Regional
What are the airports in Pensacola?
PNS
Can I make changes to my Chicago to Pensacola 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 MDW to PNS?
Read the fare rules of the Chicago to Pensacola 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 Chicago and Pensacola?
operate flights between Chicago and Pensacola
How long does a flight from Chicago to Pensacola take?
It takes approximately 2 hour to fly non-stop from MDW to PNS, which is 780.63 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Pensacola (PNS) ?
In the past couple of days, the cheapest tickets to PNS from MDW were found on DL : USD 384
Do I need a passport to fly between MDW and PNS?
No
What’s the latest departure time from MDW to PNS ?
The last flight leaves MDW at 4:22 pm

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

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

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