Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Pensacola to Chicago Midway Airport from $53

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Chicago Midway Airport departing on 2/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Pensacola to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Pensacola to Chicago.

Cheap last minute flights

Planning a quick getaway from Pensacola to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Pensacola to Chicago

Find recent round-trip train or bus tickets from Pensacola to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
7:15 am - 6:13 pmMDW-PNS
10h 58m1 stop
$128Frontier
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
$148Frontier
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
7:15 am - 6:13 pmMDW-PNS
10h 58m1 stop
$158Frontier
Find Deal
Mon, Dec 9 - Mon, Dec 16
7:27 pm - 12:17 amPNS-MDW
28h 50m1 stop
6:40 am - 6:27 pmMDW-PNS
11h 47m1 stop
$178Frontier
Find Deal
Fri, Feb 21 - Sun, Feb 23
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
7:15 am - 6:13 pmMDW-PNS
10h 58m1 stop
$198Frontier
Find Deal
Thu, Dec 12 - Sun, Dec 15
5:42 pm - 10:06 pmPNS-MDW
4h 24m1 stop
10:57 am - 5:00 pmMDW-PNS
6h 03m1 stop
$228Delta
Find Deal
Fri, Jan 3 - Mon, Jan 6
6:03 pm - 10:20 pmPNS-MDW
4h 17m1 stop
6:00 am - 9:58 amMDW-PNS
3h 58m1 stop
$263Delta
Find Deal
Thu, Feb 13 - Mon, Feb 17
11:45 am - 7:00 pmPNS-MDW
7h 15m2 stops
9:05 am - 3:25 pmMDW-PNS
6h 20m2 stops
$303Southwest
Find Deal
Mon, Jan 6 - Wed, Jan 8
8:45 am - 3:10 pmPNS-MDW
6h 25m1 stop
10:25 am - 5:25 pmMDW-PNS
7h 00m1 stop
$323Southwest
Find Deal
Mon, Jan 6 - Wed, Jan 8
5:04 pm - 4:40 pmPNS-MDW
23h 36m3 stops
5:35 pm - 6:05 pmMDW-PNS
24h 30m3 stops
$1,174
Find Deal
Sun, Dec 22 - Fri, Dec 27
5:36 pm - 12:17 amPNS-MDW
6h 41m1 stop
$53Frontier
Find Deal
Sat, Feb 22
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
$65Frontier
Find Deal
Mon, Jan 13
5:23 pm - 12:17 amPNS-MDW
6h 54m1 stop
$73Frontier
Find Deal
Wed, Feb 12
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
$75Frontier
Find Deal
Sun, Jan 26
9:20 am - 7:15 pmPNS-MDW
9h 55m1 stop
Sat, Feb 15
5:47 pm - 10:06 pmPNS-MDW
4h 19m1 stop
$114Delta
Find Deal
Wed, Dec 18
9:20 am - 7:15 pmPNS-MDW
9h 55m1 stop
Tue, Mar 4
9:38 am - 4:21 pmPNS-MDW
6h 43m1 stop
$124Delta
Find Deal
Tue, Jan 7
8:20 am - 6:35 pmPNS-MDW
10h 15m2 stops
$154Southwest
Find Deal
Wed, Jan 29
8:20 am - 7:20 pmPNS-MDW
11h 00m2 stops
$160Southwest
Find Deal
Fri, Jan 24
8:58 pm - 8:42 pmPNS-MDW
23h 44m1 stop
7:00 am - 7:58 pmMDW-PNS
12h 58m1 stop
$328Frontier
Find Deal
Sun, Nov 24 - Thu, Nov 28
1:20 pm - 7:40 pmPNS-MDW
6h 20m1 stop
6:20 am - 10:00 amMDW-PNS
3h 40m1 stop
$383Southwest
Find Deal
Sun, Nov 24 - Wed, Dec 4
5:55 pm - 11:55 pmPNS-MDW
6h 00m1 stop
6:45 am - 4:25 pmMDW-PNS
9h 40m2 stops
$388Southwest
Find Deal
Sun, Nov 24 - Thu, Nov 28
9:50 am - 6:10 pmPNS-MDW
8h 20m2 stops
6:45 am - 4:25 pmMDW-PNS
9h 40m2 stops
$393Southwest
Find Deal
Sun, Nov 24 - Thu, Nov 28
5:55 pm - 11:55 pmPNS-MDW
6h 00m1 stop
2:30 pm - 9:35 pmMDW-PNS
7h 05m1 stop
$448Southwest
Find Deal
Fri, Nov 22 - Sun, Nov 24
5:40 am - 2:25 pmPNS-MDW
8h 45m2 stops
2:30 pm - 9:35 pmMDW-PNS
7h 05m1 stop
$453Southwest
Find Deal
Fri, Nov 22 - Sun, Nov 24
5:40 am - 2:25 pmPNS-MDW
8h 45m2 stops
1:40 pm - 9:35 pmMDW-PNS
7h 55m2 stops
$458Southwest
Find Deal
Fri, Nov 22 - Sun, Nov 24
8:58 pm - 12:36 pmPNS-MDW
15h 38m1 stop
9:48 pm - 7:58 pmMDW-PNS
22h 10m1 stop
$479Frontier
Find Deal
Sat, Nov 23 - Wed, Nov 27
11:20 am - 5:54 pmPNS-MDW
6h 34m1 stop
6:00 am - 10:15 amMDW-PNS
4h 15m1 stop
$578Delta
Find Deal
Fri, Nov 22 - Sun, Nov 24
1:29 pm - 5:54 pmPNS-MDW
4h 25m1 stop
9:31 am - 7:41 pmMDW-PNS
10h 10m2 stops
$1,079Delta
Find Deal
Fri, Nov 22 - Sun, Nov 24
1:30 pm - 3:45 pmPNS-MDW
2h 15mnonstop
9:25 am - 11:40 amMDW-PNS
2h 15mnonstop
$599Southwest
Find Deal
Fri, Mar 21 - Sun, Mar 23

Frontier flights from Pensacola to Chicago Midway Airport

Our best Frontier deals on Pensacola to Chicago Midway Airport flight tickets
Frontier
Jan 9
PNS7:17 pmPensacola
28h 56m
1 stop
MDW12:13 amChicago Midway
Jan 12
MDW7:15 amChicago Midway
10h 58m
1 stop
PNS6:13 pmPensacola
Frontier
Jan 16
PNS7:17 pmPensacola
29h 00m
1 stop
MDW12:17 amChicago Midway
Jan 19
MDW7:15 amChicago Midway
11h 02m
1 stop
PNS6:17 pmPensacola
Frontier
Dec 9
PNS7:17 pmPensacola
28h 56m
1 stop
MDW12:13 amChicago Midway
Dec 16
MDW7:15 amChicago Midway
10h 58m
1 stop
PNS6:13 pmPensacola

Delta flights from Pensacola to Chicago Midway Airport

Our best Delta deals on Pensacola to Chicago Midway Airport flight tickets
Delta
Jan 3
PNS5:42 pmPensacola
4h 24m
1 stop
MDW10:06 pmChicago Midway
Jan 6
MDW10:57 amChicago Midway
6h 03m
1 stop
PNS5:00 pmPensacola
Delta
Feb 13
PNS6:03 pmPensacola
4h 17m
1 stop
MDW10:20 pmChicago Midway
Feb 17
MDW6:00 amChicago Midway
3h 58m
1 stop
PNS9:58 amPensacola
Delta
Dec 13
PNS5:47 pmPensacola
4h 19m
1 stop
MDW10:06 pmChicago Midway
Dec 16
MDW6:00 amChicago Midway
4h 06m
1 stop
PNS10:06 amPensacola

See travel insights to Chicago from

How to get the cheapest flight ticket from Pensacola to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Pensacola, with most prices found around $207. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Pensacola during the month April is also very affordable. Most momondo users find prices during this month for around $218.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Monday departure recently was $0. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Wednesday is the most expensive day to depart from Pensacola because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $488.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Pensacola in the evening is the least expensive time of day to depart. momondo users have found prices as low as $0 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $430. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Pensacola to Chicago Midway flight route?

Fly from Pensacola to Chicago Midway for the best Pensacola - Chicago Midway flight prices

What cabin class options are available on Pensacola to Chicago Midway flights?

There are 1 cabin classes available to choose from on Pensacola to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Pensacola to Chicago Midway Airport flights?

You could potentially save up to 67% on your flight if you consider stops on a Pensacola to Chicago Midway Airport flight.

When to book flights from Pensacola to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Pensacola to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Pensacola to Chicago Midway Airport (PNS to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pensacola to Chicago Midway Airport

Best Price Found

$53

Fastest flight time

2h 15m

Direct flights

Mon, Tue, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Pensacola in the past 72 hours is $53. The best round-trip flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $128.
The fastest flight from Pensacola to Chicago Midway Airport takes 2h 15m
Direct flights go from Pensacola to Chicago Midway Airport on Monday, Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.

  • How far is Pensacola to Chicago Midway by plane?

    The distance between Pensacola and Chicago Midway is about 785.3 mi. Flights usually cover this in 2h 15m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Pensacola Airport to Chicago Midway Airport?

    Prices for flights from Pensacola Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Pensacola Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Pensacola Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Pensacola Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Pensacola to Chicago Midway Airport?

  • What is the most popular airline from Pensacola to Chicago Midway Airport?


Best airlines flying from Pensacola to Chicago Midway Airport

Compare and see reviews for airlines that fly from Pensacola to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $207Free CancellationRating
8.0
8,755 reviews
Search Delta flights
SouthwestPriceFrom $263Free CancellationRating
8.1
5,005 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Pensacola to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Pensacola.

Can I find flights from Pensacola to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Pensacola with this policy.

How can momondo help me find flights from Pensacola to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Pensacola. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Pensacola to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Pensacola to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

Find better results for your trip to Chicago