What is the cheapest airline that flies from Chicago Midway to Pensacola?

Delta is the most popular carrier operating from Chicago Midway to Pensacola

How many flights depart from Chicago Midway Airport to Pensacola on average per week?

As of December 2025, there are 4 flights per week flying from Chicago Midway Airport to Pensacola. The most common day of the week flights depart is Mon, with 25% of flights taking off on this day.

What airlines fly to Pensacola?

Southwest, Allegiant Air and Delta are the top three most popular airlines that fly to Pensacola from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Pensacola. Keep in mind that there are 3 different airlines that fly to Pensacola on a routine basis, so you have a few additional options to choose from.

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?

As of December 2025, there are 2 operators available to choose from 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.

$89 Cheap Flights from Chicago Midway Airport to Pensacola in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago Midway Airport to Pensacola

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:40 am - 3:40 pm

MDW

PNS

8h 00m1 stop

5:20 pm - 7:35 pm

PNS

MDW

2h 15mnonstop

$225Southwest

Sat, Mar 14 - Wed, Mar 18

6:00 am - 12:30 pm

MDW

PNS

6h 30m1 stop

7:00 am - 11:59 am

PNS

MDW

4h 59m1 stop

$229Delta

Wed, Feb 18 - Tue, Feb 24

6:50 am - 4:05 pm

MDW

PNS

9h 15m1 stop

10:15 am - 5:55 pm

PNS

MDW

7h 40m1 stop

$234Southwest

Sat, Feb 14 - Sat, Feb 21

9:38 am - 4:37 pm

MDW

PNS

30h 59m2 stops

5:50 pm - 2:26 pm

PNS

MDW

20h 36m1 stop

$237Multiple Airlines

Sat, Feb 7 - Thu, Feb 12

1:00 pm - 4:37 pm

MDW

PNS

27h 37m1 stop

5:33 pm - 8:43 am

PNS

MDW

15h 10m2 stops

$239Multiple Airlines

Sun, Feb 1 - Fri, Feb 6

6:50 am - 4:05 pm

MDW

PNS

9h 15m1 stop

10:15 am - 5:10 pm

PNS

MDW

6h 55m2 stops

$240Southwest

Sat, Feb 14 - Sat, Feb 21

5:25 am - 9:25 am

MDW

PNS

4h 00m1 stop

4:25 pm - 10:30 pm

PNS

MDW

6h 05m1 stop

$243Southwest

Thu, Feb 19 - Mon, Feb 23

1:00 pm - 4:37 pm

MDW

PNS

27h 37m1 stop

7:31 pm - 12:05 pm

PNS

MDW

16h 34m2 stops

$245Multiple Airlines

Fri, Jan 23 - Mon, Jan 26

2:35 pm - 6:25 pm

MDW

PNS

3h 50m1 stop

7:45 am - 4:55 pm

PNS

MDW

9h 10m2 stops

$248Southwest

Thu, Jan 8 - Sat, Jan 10

10:10 am - 4:45 pm

MDW

PNS

6h 35m1 stop

3:00 pm - 7:45 pm

PNS

MDW

4h 45m1 stop

$249Southwest

Thu, Mar 5 - Sun, Mar 8

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets

Southwest

Mar 14

MDW7:40 amChicago Midway

8h 00m

1 stop

PNS3:40 pmPensacola

Mar 18

PNS5:20 pmPensacola

2h 15m

MDW7:35 pmChicago Midway

$225

Find similar

Southwest

Feb 14

MDW6:50 amChicago Midway

9h 15m

1 stop

PNS4:05 pmPensacola

Feb 21

PNS10:15 amPensacola

7h 40m

1 stop

MDW5:55 pmChicago Midway

$234

Find similar

Southwest

Feb 14

MDW6:50 amChicago Midway

9h 15m

1 stop

PNS4:05 pmPensacola

Feb 21

PNS10:15 amPensacola

6h 55m

2 stops

MDW5:10 pmChicago Midway

$240

Find similar

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets

Delta

Feb 18

MDW6:00 amChicago Midway

6h 30m

1 stop

PNS12:30 pmPensacola

Feb 24

PNS7:00 amPensacola

4h 59m

1 stop

MDW11:59 amChicago Midway

$229

Find similar

Delta

Jan 16

MDW5:31 pmChicago Midway

5h 42m

1 stop

PNS11:13 pmPensacola

Jan 19

PNS4:04 pmPensacola

6h 18m

1 stop

MDW10:22 pmChicago Midway

$279

Find similar

Delta

Dec 18

MDW10:49 amChicago Midway

6h 01m

1 stop

PNS4:50 pmPensacola

Jan 6

PNS5:54 pmPensacola

4h 13m

1 stop

MDW10:07 pmChicago Midway

$309

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 3/14

7:40 am-3:40 pm

1 stop8h 00m

Pensacola

Wed 3/18

5:20 pm-7:35 pm

Nonstop2h 15m

$225

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Tue 2/24

7:00 am-11:59 am

1 stop4h 59m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/14

6:50 am-4:05 pm

1 stop9h 15m

Pensacola

Sat 2/21

10:15 am-5:55 pm

1 stop7h 40m

$234

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/7

9:38 am-4:37 pm

2 stops30h 59m

Pensacola

Thu 2/12

5:50 pm-2:26 pm

1 stop20h 36m

$237

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 2/1

1:00 pm-4:37 pm

1 stop27h 37m

Pensacola

Fri 2/6

5:33 pm-8:43 am

2 stops15h 10m

$239

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/14

6:50 am-4:05 pm

1 stop9h 15m

Pensacola

Sat 2/21

10:15 am-5:10 pm

2 stops6h 55m

$240

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 2/19

5:25 am-9:25 am

1 stop4h 00m

Pensacola

Mon 2/23

4:25 pm-10:30 pm

1 stop6h 05m

$243

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/23

1:00 pm-4:37 pm

1 stop27h 37m

Pensacola

Mon 1/26

7:31 pm-12:05 pm

2 stops16h 34m

$245

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 1/8

2:35 pm-6:25 pm

1 stop3h 50m

Pensacola

Sat 1/10

7:45 am-4:55 pm

2 stops9h 10m

$248

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 3/5

10:10 am-4:45 pm

1 stop6h 35m

Pensacola

Sun 3/8

3:00 pm-7:45 pm

1 stop4h 45m

$249

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $318. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Saturday 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 $390.

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 $323. Flights to Pensacola are more costly in the afternoon, with an average ticket price of $587. 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 to Pensacola flights?

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

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

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

Fastest flight time	2h 10m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Pensacola	1 airport

The fastest flight from Chicago Midway Airport to Pensacola takes 2h 10m

Direct flights go from Chicago Midway Airport to Pensacola on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There is 1 airport in Pensacola. From Chicago Midway Airport there are direct flights to Pensacola (PNS).

Search flight deals

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 2h 10m.
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?
As of December 2025, there are 2 operators available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Pensacola is Airbus A320-100/200, representing 18.52% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 14.81%, Airbus A319 at 11.11%, and Boeing 737 MAX 8 at 7.41%.
What is the most popular airline from Chicago Midway Airport to Pensacola?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Pensacola is Southwest, representing 75% of all bookings. The subsequent popular airline is Delta at 25%.

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
Delta	PriceFrom $196	Free Cancellation	Rating 7.9 8,008 reviews		Search Delta flights
Southwest	PriceFrom $216	Free Cancellation	Rating 7.9 4,253 reviews		Search Southwest flights

Southwest Flights From Chicago Midway Airport to Pensacola
Southwest is one of the most popular airlines flying from Chicago Midway Airport to Pensacola, operating 4 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Pensacola starts from $216 round-trip, up to an average price of $361. Our users have rated Southwest at 7.9/10.

Orange Beach

Pensacola Beach

Foley

Perdido Key

Navarre

Navarre Beach

Atmore

Milton

Gulf Breeze

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.

An easier way to manage your Pensacola 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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sat 1/10

Sat 1/17

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Airports servicing Florida

Popular cities in the United States

Flights to New Yorkfrom $34

Flights to Los Angelesfrom $49

Flights to Miamifrom $49

Flights to Chicagofrom $49

Flights to Orlandofrom $41

Flights to San Franciscofrom $53

Flights to Las Vegasfrom $40

Flights to Washington, D.C.from $49

Flights to Bostonfrom $55

Flights to Atlantafrom $49

Flights to Dallasfrom $52

Flights to Seattlefrom $58

Cheap flights from Chicago Midway Airport to Pensacola from $89

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago Midway Airport to Pensacola

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets

momondo Fare Finder

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

See travel insights to Pensacola from

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

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

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

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 to Pensacola flights?

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

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

What is the cheapest airline that flies from Chicago Midway to Pensacola?

Delta is the most popular carrier operating from Chicago Midway to Pensacola

What airlines fly to Pensacola?

How many flights depart from Chicago Midway Airport to Pensacola on average per week?

As of December 2025, there are 4 flights per week flying from Chicago Midway Airport to Pensacola. The most common day of the week flights depart is Mon, with 25% of flights taking off on this day.

When to book flights from Chicago Midway Airport to Pensacola

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

Fastest flight time

Direct flights

Airports in Pensacola

How far is Chicago Midway to Pensacola by plane?

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

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?

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

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

Southwest Flights From Chicago Midway Airport to Pensacola

Traveling to a place near Pensacola?

Why use momondo?

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

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

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

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

An easier way to manage your Pensacola 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.

Find better results for your trip to the United States

Airports servicing Florida