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Cheap flights from Pensacola to Chicago from $141

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
9:40 am - 2:20 pmPNS  Pensacola-MDW Chicago Midway
4h 40m1 stop Dallas Love Field
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$290Southwest
Sat, Sep 19 - Wed, Sep 30
Southwest Logo
4:20 pm - 8:10 pmPNS  Pensacola-MDW Chicago Midway
3h 50m1 stop Nashville Intl
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$294Southwest
Tue, Sep 22 - Tue, Sep 29
Southwest Logo
6:15 pm - 9:55 pmPNS  Pensacola-MDW Chicago Midway
3h 40m1 stop Lambert-St Louis
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$294Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
4:20 pm - 8:10 pmPNS  Pensacola-MDW Chicago Midway
3h 50m1 stop Nashville Intl
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$294Southwest
Tue, Sep 15 - Tue, Sep 22
Southwest Logo
7:55 am - 1:30 pmPNS  Pensacola-MDW Chicago Midway
5h 35m1 stop Nashville Intl
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$294Southwest
Tue, Sep 15 - Tue, Sep 22
Delta Logo
9:26 am - 4:15 pmPNS  Pensacola-MDW Chicago Midway
6h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-PNS Pensacola
6h 34m1 stop Atlanta Hartsfield-Jackson
$299Delta
Tue, Sep 22 - Mon, Sep 28
Delta Logo
8:10 am - 11:54 amPNS  Pensacola-MDW Chicago Midway
3h 44m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:11 pm - 11:21 pmMDW  Chicago Midway-PNS Pensacola
6h 10m1 stop Atlanta Hartsfield-Jackson
$299Delta
Wed, Sep 30 - Wed, Sep 30
Delta Logo
5:30 pm - 10:44 pmPNS  Pensacola-MDW Chicago Midway
5h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:48 am - 3:02 pmMDW  Chicago Midway-PNS Pensacola
4h 14m1 stop Atlanta Hartsfield-Jackson
$299Delta
Sat, Sep 26 - Thu, Oct 1
Delta Logo
6:00 am - 10:03 amPNS  Pensacola-MDW Chicago Midway
4h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 10:52 amMDW  Chicago Midway-PNS Pensacola
4h 48m1 stop Atlanta Hartsfield-Jackson
$299Delta
Thu, Oct 22 - Tue, Oct 27
Multiple Airlines Logo
1:10 pm - 6:26 pmPNS  Pensacola-MDW Chicago Midway
29h 16m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:07 pm - 11:28 amMDW  Chicago Midway-PNS Pensacola
15h 21m1 stop Orlando
$647Multiple Airlines
Sun, Nov 29 - Sun, Dec 6

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Delta flights from Pensacola to Chicago Midway Airport

Our best Delta deals on Pensacola to Chicago Midway Airport flight tickets
Delta
Sep 22
PNS9:26 amPensacola
6h 49m
1 stop
MDW4:15 pmChicago Midway
Sep 28
MDW6:05 amChicago Midway
6h 34m
1 stop
PNS12:39 pmPensacola
$299
Delta
Sep 21
PNS5:51 pmPensacola
4h 53m
1 stop
MDW10:44 pmChicago Midway
Sep 28
MDW6:05 amChicago Midway
6h 34m
1 stop
PNS12:39 pmPensacola
$319
Delta
Sep 22
PNS9:26 amPensacola
6h 49m
1 stop
MDW4:15 pmChicago Midway
Oct 1
MDW1:00 pmChicago Midway
6h 09m
1 stop
PNS7:09 pmPensacola
$349

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Sep 19
PNS9:40 amPensacola
4h 40m
1 stop
MDW2:20 pmChicago Midway
Sep 30
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
$290
Southwest
Sep 15
PNS7:55 amPensacola
5h 35m
1 stop
MDW1:30 pmChicago Midway
Sep 22
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
$294
Southwest
Sep 15
PNS7:55 amPensacola
7h 55m
2 stops
MDW3:50 pmChicago Midway
Sep 22
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
$300

momondo Fare Finder

 
Use the filters below to find and compare flights from Pensacola to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Sat 9/19

9:40 am-2:20 pm

1 stop4h 40m

Chicago Midway

Wed 9/30

2:00 pm-5:35 pm

1 stop3h 35m

$290

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Tue 9/22

4:20 pm-8:10 pm

1 stop3h 50m

Chicago Midway

Tue 9/29

2:00 pm-5:35 pm

1 stop3h 35m

$294
Quickest round-trip

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Wed 9/16

6:15 pm-9:55 pm

1 stop3h 40m

Chicago Midway

Tue 9/22

2:00 pm-5:35 pm

1 stop3h 35m

$294

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Tue 9/15

4:20 pm-8:10 pm

1 stop3h 50m

Chicago Midway

Tue 9/22

2:00 pm-5:35 pm

1 stop3h 35m

$294

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Tue 9/15

7:55 am-1:30 pm

1 stop5h 35m

Chicago Midway

Tue 9/22

2:00 pm-5:35 pm

1 stop3h 35m

$294

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Tue 9/22

9:26 am-4:15 pm

1 stop6h 49m

Chicago Midway

Mon 9/28

6:05 am-12:39 pm

1 stop6h 34m

$299

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Wed 9/30

8:10 am-11:54 am

1 stop3h 44m

Chicago Midway

Wed 9/30

5:11 pm-11:21 pm

1 stop6h 10m

$299

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Sat 9/26

5:30 pm-10:44 pm

1 stop5h 14m

Chicago Midway

Thu 10/1

10:48 am-3:02 pm

1 stop4h 14m

$299

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Thu 10/22

6:00 am-10:03 am

1 stop4h 03m

Chicago Midway

Tue 10/27

6:04 am-10:52 am

1 stop4h 48m

$299

PensacolaChicago

PNS Pensacola - MDW Chicago Midway

PNSMDW

Pensacola

Sun 11/29

1:10 pm-6:26 pm

2 stops29h 16m

Chicago Midway

Sun 12/6

8:07 pm-11:28 am

1 stop15h 21m

$647

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Pensacola and Chicago Midway Airport?

Prices are currently typical for flights on this route.

Typical prices usually range from $263 to $554.
The lowest price recently found on this route was $290.

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

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Pensacola, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Pensacola during the month February is also very affordable. Most momondo users find prices during this month for around $0.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Saturday departure recently was $400. 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, Monday 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 $567.

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

Flying to Chicago Midway Airport from Pensacola at noon is the least expensive time of day to depart. momondo users have found prices as low as $400 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $466. 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 Airport flights?

There is only 1 cabin class available to choose from on Pensacola to Chicago Midway Airport 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?

No. A direct flight is the cheapest option for a flight between Pensacola to Chicago Midway Airport.

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

$141

Fastest flight time

3h 50m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Pensacola in the past 72 hours is $141. The best round-trip flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $290.
The fastest flight from Pensacola to Chicago Midway Airport takes 3h 50m
There are no direct flights from Pensacola to Chicago Midway Airport. There are no popular flight routes from Pensacola to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Pensacola to Chicago Midway Airport

  • 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 3h 50m, 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 $228Free CancellationRating
7.8
8,518 reviews
Search Delta flights
SouthwestPriceFrom $237Free CancellationRating
8.0
4,211 reviews
Search Southwest flights

  • Southwest Flights From Pensacola to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Pensacola to Chicago Midway Airport, operating 2 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago Midway Airport starts from $237 round-trip, up to an average price of $397. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

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.

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