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Cheap flights from Chicago Midway Airport to Pensacola from $145

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Pensacola

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
Southwest Logo
6:15 pm - 9:55 pmPNS  Pensacola-MDW Chicago Midway
3h 40m1 stop Lambert-St Louis
$294Southwest
Tue, Sep 22 - Tue, Sep 29
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
Southwest Logo
4:20 pm - 8:10 pmPNS  Pensacola-MDW Chicago Midway
3h 50m1 stop Nashville Intl
$294Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
Southwest Logo
4:20 pm - 10:25 pmPNS  Pensacola-MDW Chicago Midway
6h 05m1 stop Nashville Intl
$294Southwest
Tue, Sep 15 - Tue, Sep 22
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-PNS Pensacola
6h 34m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:26 am - 4:15 pmPNS  Pensacola-MDW Chicago Midway
6h 49m1 stop Atlanta Hartsfield-Jackson
$299Delta
Wed, Sep 16 - Tue, Sep 22
Delta Logo
11:33 am - 5:23 pmMDW  Chicago Midway-PNS Pensacola
5h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:40 pm - 10:33 pmPNS  Pensacola-MDW Chicago Midway
4h 53m1 stop Atlanta Hartsfield-Jackson
$299Delta
Sat, Oct 10 - Sat, Oct 17
Southwest Logo
5:30 am - 1:30 pmMDW  Chicago Midway-PNS Pensacola
8h 00m1 stop Austin Bergstrom
Southwest Logo
1:45 pm - 8:10 pmPNS  Pensacola-MDW Chicago Midway
6h 25m1 stop Houston Hobby
$299Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
6:35 am - 10:10 amMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
Southwest Logo
1:45 pm - 6:35 pmPNS  Pensacola-MDW Chicago Midway
4h 50m1 stop Houston Hobby
$299Southwest
Sat, Sep 26 - Mon, Sep 28
Southwest Logo
5:30 am - 1:30 pmMDW  Chicago Midway-PNS Pensacola
8h 00m1 stop Austin Bergstrom
Southwest Logo
1:45 pm - 8:10 pmPNS  Pensacola-MDW Chicago Midway
6h 25m1 stop Houston Hobby
$299Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
6:50 am - 2:55 pmMDW  Chicago Midway-PNS Pensacola
8h 05m1 stop Denver Intl
Southwest Logo
6:15 pm - 9:55 pmPNS  Pensacola-MDW Chicago Midway
3h 40m1 stop Lambert-St Louis
$299Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
10:25 am - 4:15 pmMDW  Chicago Midway-PNS Pensacola
5h 50m1 stop Houston Hobby
Southwest Logo
12:15 pm - 7:55 pmPNS  Pensacola-MDW Chicago Midway
7h 40m1 stop Houston Hobby
$299Southwest
Sat, Sep 26 - Sat, Oct 3

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Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
Sep 15
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
Sep 22
PNS4:20 pmPensacola
6h 05m
1 stop
MDW10:25 pmChicago Midway
$294
Southwest
Sep 26
MDW6:50 amChicago Midway
8h 05m
1 stop
PNS2:55 pmPensacola
Sep 29
PNS6:15 pmPensacola
3h 40m
1 stop
MDW9:55 pmChicago Midway
$299
Southwest
Sep 15
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
Sep 22
PNS7:55 amPensacola
7h 30m
2 stops
MDW3:25 pmChicago Midway
$300

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
Sep 26
MDW6:05 amChicago Midway
4h 34m
1 stop
PNS10:39 amPensacola
Oct 3
PNS6:00 amPensacola
4h 36m
1 stop
MDW10:36 amChicago Midway
$319
Delta
Sep 11
MDW11:35 amChicago Midway
5h 36m
1 stop
PNS5:11 pmPensacola
Sep 18
PNS5:35 pmPensacola
5h 09m
1 stop
MDW10:44 pmChicago Midway
$339
Delta
Sep 14
MDW6:05 amChicago Midway
6h 34m
1 stop
PNS12:39 pmPensacola
Sep 24
PNS6:00 amPensacola
3h 49m
1 stop
MDW9:49 amChicago Midway
$349

momondo Fare Finder

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

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Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Tue 9/22

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Tue 9/29

6:15 pm-9:55 pm

1 stop3h 40m

$294

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Wed 9/16

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Wed 9/23

4:20 pm-8:10 pm

1 stop3h 50m

$294

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Tue 9/15

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Tue 9/22

4:20 pm-10:25 pm

1 stop6h 05m

$294

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Wed 9/16

6:05 am-12:39 pm

1 stop6h 34m

Pensacola

Tue 9/22

9:26 am-4:15 pm

1 stop6h 49m

$299

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Sat 10/10

11:33 am-5:23 pm

1 stop5h 50m

Pensacola

Sat 10/17

5:40 pm-10:33 pm

1 stop4h 53m

$299

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Fri 9/25

5:30 am-1:30 pm

1 stop8h 00m

Pensacola

Mon 9/28

1:45 pm-8:10 pm

1 stop6h 25m

$299

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Sat 9/26

6:35 am-10:10 am

1 stop3h 35m

Pensacola

Mon 9/28

1:45 pm-6:35 pm

1 stop4h 50m

$299

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Mon 9/21

5:30 am-1:30 pm

1 stop8h 00m

Pensacola

Mon 9/28

1:45 pm-8:10 pm

1 stop6h 25m

$299

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Sat 9/26

6:50 am-2:55 pm

1 stop8h 05m

Pensacola

Tue 9/29

6:15 pm-9:55 pm

1 stop3h 40m

$299

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Sat 9/26

10:25 am-4:15 pm

1 stop5h 50m

Pensacola

Sat 10/3

12:15 pm-7:55 pm

1 stop7h 40m

$299

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 Pensacola from

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

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 Pensacola?

The cheapest month to fly to Pensacola from Chicago Midway Airport is in November. Flight prices, which tend to average around $132, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Pensacola from Chicago Midway Airport during February instead. Flights to Pensacola in February, while not as cheap as those in November, still average around $311.

What is the cheapest day to depart on your flight to Pensacola?

On average, the least expensive day to fly to Pensacola from Chicago Midway Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $340. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $437.

What is the cheapest time of day to depart on your flight to Pensacola?

The cheapest time of day to fly to Pensacola is at noon when flights can be purchased for as low as $352. Flights to Pensacola are more costly in the afternoon, with an average ticket price of $403. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Pensacola flight route?

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

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

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

You could potentially save up to 6% on your flight if you consider stops on a Chicago Midway Airport to Pensacola flight.

When to book flights from Chicago Midway Airport to Pensacola

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

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

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

Best Price Found

$145

Fastest flight time

4h 09m

Direct flights

None
The best one-way flight to Pensacola from Chicago Midway Airport in the past 72 hours is $145. The best round-trip flight deal from Chicago Midway Airport to Pensacola found on momondo in the last 72 hours is $294.
The fastest flight from Chicago Midway Airport to Pensacola takes 4h 09m
There are no direct flights from Chicago Midway Airport to Pensacola. There are no popular flight routes from Chicago Midway Airport to Pensacola.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Pensacola

  • How far is Chicago Midway to Pensacola by plane?

    Chicago Midway and Pensacola are 785.3 mi apart from one another. A reasonable flight in good conditions will take 4h 09m.

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

    Prices for flights from Chicago Midway Airport to Pensacola Airport are refreshed on a daily basis.

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

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

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

    The necessary travel and health documents for your Pensacola Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Chicago Midway Airport to Pensacola

Compare and see reviews for airlines that fly from Chicago Midway Airport to Pensacola with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $227Free CancellationRating
7.8
8,539 reviews
Search Delta flights
SouthwestPriceFrom $278Free CancellationRating
8.0
4,201 reviews
Search Southwest flights

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Orange Beach
Pensacola Beach
Foley
Navarre Beach
Navarre
Atmore
Gulf Breeze
Perdido Key
Milton
Evergreen
Warrington

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Pensacola for you.

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

All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.

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

Once all potential Chicago to Pensacola flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to Pensacola flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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