Skyscanner home

Cheap Flights from Pensacola (PNS) to Chicago (MDW)

Compare Pensacola to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Pensacola to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Pensacola Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $416. Find the lowest prices on one-way and return tickets right here.
Chicago.$410 per passenger.Departing Sat, 29 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Sat, 29 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 1 Sep, arriving in Pensacola.Price includes taxes and charges.From $410, select.
Chicago.$416 per passenger.Departing Sat, 22 Aug, returning Tue, 25 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Sat, 22 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 25 Aug, arriving in Pensacola.Price includes taxes and charges.From $416, select.
Chicago.$417 per passenger.Departing Sat, 12 Sep, returning Sat, 19 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Sat, 12 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 19 Sep, arriving in Pensacola.Price includes taxes and charges.From $417, select.
Chicago.$424 per passenger.Departing Thu, 19 Nov, returning Thu, 26 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Thu, 19 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 26 Nov, arriving in Pensacola.Price includes taxes and charges.From $424, select.
Chicago.$424 per passenger.Departing Sat, 26 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Sat, 26 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 1 Oct, arriving in Pensacola.Price includes taxes and charges.From $424, select.
Chicago.$424 per passenger.Departing Thu, 22 Oct, returning Sat, 24 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Thu, 22 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 24 Oct, arriving in Pensacola.Price includes taxes and charges.From $424, select.
Chicago.$424 per passenger.Departing Wed, 2 Dec, returning Wed, 9 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Wed, 2 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 9 Dec, arriving in Pensacola.Price includes taxes and charges.From $424, select.
Chicago.$474 per passenger.Departing Thu, 4 Feb, returning Thu, 11 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Thu, 4 Feb, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 11 Feb, arriving in Pensacola.Price includes taxes and charges.From $474, select.
Chicago.$502 per passenger.Departing Wed, 25 Nov, returning Wed, 2 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Wed, 25 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 2 Dec, arriving in Pensacola.Price includes taxes and charges.From $502, select.
Chicago.$669 per passenger.Departing Thu, 11 Mar, returning Sun, 14 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pensacola on Thu, 11 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 14 Mar, arriving in Pensacola.Price includes taxes and charges.From $669, select.
Chicago.$729 per passenger.Departing Tue, 28 Jul, returning Tue, 4 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Tue, 28 Jul, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 4 Aug, arriving in Pensacola.Price includes taxes and charges.From $729, select.
Chicago.$810 per passenger.Departing Sat, 25 Jul, returning Sun, 26 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pensacola on Sat, 25 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 26 Jul, arriving in Pensacola.Price includes taxes and charges.From $810, select.
Chicago.$813 per passenger.Departing Sat, 1 Aug, returning Mon, 3 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pensacola on Sat, 1 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 3 Aug, arriving in Pensacola.Price includes taxes and charges.From $813, select.
Chicago.$813 per passenger.Departing Wed, 29 Jul, returning Mon, 3 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Pensacola on Wed, 29 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 3 Aug, arriving in Pensacola.Price includes taxes and charges.From $813, select.
Chicago.$1,505 per passenger.Departing Sun, 27 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Pensacola on Sun, 27 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 2 Jan, arriving in Pensacola.Price includes taxes and charges.From $1,505, select.

Find the cheapest month to fly from Pensacola to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Pensacola to Chicago Midway flights are currently cheapest in August.
Jul
from $810
Aug
from $416
Sep
from $417
Oct
from $424
Nov
from $424
Dec
from $424
Jan
Find prices
Feb
from $474
Mar
from $669
Apr
Find prices
May
Find prices
Jun
Find prices

Direct flights from Pensacola to Chicago Midway

Pensacola to Chicago Midway: Alternative routes

Compare routes from Pensacola to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
Closest
from $410
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $353
Search flights

Chicago Rockford

127km from central Chicago
from $399
Search flights

Pensacola to Chicago: Flight information

The things to know before you go.
Cheapest flight found$410
Cheapest month to flyAugust
Average flight time2 hrs, 18 mins
Most popular airlineSouthwest Airlines
Average flights per week8

Finding cheap flights from Pensacola to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Pensacola to Chicago Midway is $410. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 18 minutes is the average flight time from Pensacola to Chicago Midway.
Southwest Airlines flies direct from Pensacola to Chicago Midway.
As of July 2026, there are 8 flights per week flying from Pensacola to Chicago Midway.
The cheapest month to fly from Pensacola to Chicago Midway is usually August.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Pensacola Airport to Chicago Midway Airport on Saturday, 29 August 2026.
Yes – the average flight time is 2 hours and 18 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Pensacola Airport (PNS) to Chicago Midway Airport (MDW): what you need to know

  • Around 2 hours 15 minutes is how long you can expect to be travelling on a direct flight from Pensacola Airport to Chicago Midway Airport.

  • Pensacola and Chicago are in the same timezone, UTC-6.

  • Your PNS to MDW flight won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

  • You can expect longer lines in popular months like July. Arriving up to four hours in advance for international flights and two hours for domestic departures is a good idea.

  • Southwest Airlines has direct flights from Pensacola Airport to Chicago Midway Airport. Book with this popular carrier, then get ready to discover the sights in Chicago — and maybe even more of the United States if you have time.

  • The airline with the highest passenger demand on this route is Southwest Airlines.

  • Think about adding a stopover when booking your ticket from Pensacola Airport to Chicago Midway Airport. Simply deselect 'Direct flights only' to break up your trip, or even explore someplace new along the way. Here's where you can stop between PNS and MDW:

    • Atlanta Hartsfield-Jackson Airport

    • Nashville Airport

    • Kansas City International Airport

How to find the cheapest flights from Pensacola Airport (PNS) to Chicago Midway Airport (MDW)

  • The cheapest price we've seen for a one-way Pensacola Airport to Chicago Midway Airport flight is $211. A round-trip fare right now is $410. Depending on the availability and when you book, these fares can change.

  • Get cheap tickets from PNS to MDW by booking one month ahead. Based on our research, that's the sweet spot for finding the biggest deals.

  • June is the cheapest month for flights from Pensacola Airport to Chicago Midway Airport. If you want to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • Cut down on the time spent looking for cheap flights from PNS to MDW by setting up a Price Alert. We'll send you an email or notification through the app when a lower fare pops up.

  • Secure the perfect flight for you by using the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Pensacola Airport to Chicago Midway Airport, use the 'Sort by' tool. You can also filter results by arrival and departure times, airline, and journey duration.

Handy information about Pensacola Airport (PNS)

  • PNS is located at 2430 Airport Boulevard.

  • Pensacola Airport has an excellent on-time record, so flight disruptions are less likely. Departures from PNS arrive on schedule 80% of the time.

  • To reach Pensacola Airport from central Pensacola, it'll take about 15 minutes if you're planning to drive. Of course, this depends on traffic conditions. It's approximately 11 kilometres from the airport to the city centre.

  • Catching public transport? Expect a trip time of around 35 minutes.

  • Get your travels off to a relaxed start by staying near PNS. Whether you're taking an early flight from Pensacola Airport to Chicago Midway Airport or just don't want to be rushed, these hotels are the answer:

Arriving at Chicago Midway Airport (MDW)

Getting from Chicago Midway Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • Chicago Midway Airport is approximately 16 kilometres from central Chicago. Driving there takes about 25 minutes.

  • Getting to the centre on public transport takes around 30 minutes.

When to fly to Chicago Midway Airport (MDW)

  • July is the busiest month for flights from Pensacola Airport to Chicago Midway Airport. To escape the crowds, head to Chicago in December.

  • Lock in your flight from Pensacola Airport to Chicago Midway Airport for July if you want to go to Chicago during its warmest month. You can expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

  • Look for cheap tickets from PNS to MDW in January if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of the United States

  • Chicago is easy to fall in love with, but there are so many other corners of the United States waiting to be explored. About 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the move. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If you're ready to explore another well-known destination in the United States, consider Indianapolis, roughly 257 kilometres south-east of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are the start of reasons to visit.

Plan smart, explore more

Where should Australians travel this year?

What are the cheapest days and weeks to fly?

5 best premium economy airlines worth paying for

How to search for multi-city flights with Skyscanner

Plan the rest of your trip from Pensacola to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.