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

As of December 2025, there are 19 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

Which layover airport offers the lowest fares from Chicago to Pensacola?

Flights via Denver (DEN) offer the lowest average round-trip price of $170.

Which layover airport has the shortest connection time from Chicago to Pensacola?

Charlotte (CLT) has the shortest average layover time for this route: 0h 51m.

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

Delta is the most popular carrier operating from Chicago to Pensacola

What airlines fly to Pensacola?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Pensacola from Chicago according to our data. United Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Pensacola. Keep in mind that there are 6 different airlines that fly to Pensacola on a routine basis, so you have a few additional options to choose from.

Which layover airport has the shortest travel time from Chicago to Pensacola?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 4h 25m.

Which airport is the most popular layover for flights between Chicago and Pensacola?

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

How many flights depart from Chicago to Pensacola on average per day?

The number of flights available between Chicago and Pensacola is 2 per day as of December 2025. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

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

Prices for flights from Chicago to Pensacola Airport refresh daily.

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

As of December 2025, there are 5 operators available to choose from for flights from Chicago to Pensacola Airport.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Pensacola Airport.

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

The travel and health documents required for your trip to Pensacola Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Pensacola Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$70 Cheap Flights from Chicago to Pensacola in 2025/26

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1:45 pm - 6:25 pmORD-PNS

4h 40m1 stop

7:50 am - 9:50 pmPNS-ORD

14h 00m2 stops

$214Southwest

Find Deal

jue., ene. 29 - lun., feb. 2

10:00 am - 1:13 pmORD-PNS

27h 13m2 stops

7:09 pm - 3:42 pmPNS-ORD

20h 33m1 stop

$215Multiple Airlines

Find Deal

mar., dic. 16 - lun., dic. 22

6:15 am - 6:14 pmORD-PNS

11h 59m1 stop

4:44 pm - 11:28 amPNS-ORD

18h 44m1 stop

$218Multiple Airlines

Find Deal

jue., dic. 11 - sáb., dic. 13

8:10 am - 3:26 pmORD-PNS

7h 16m1 stop

1:16 pm - 3:57 pmPNS-ORD

2h 41mnonstop

$221American Airlines

Find Deal

mar., feb. 17 - vie., feb. 20

7:10 am - 1:13 pmORD-PNS

6h 03m1 stop

2:08 pm - 12:09 amPNS-ORD

10h 01m1 stop

$222Spirit Airlines

Find Deal

mié., dic. 10 - mar., dic. 16

7:20 am - 3:08 pmORD-PNS

7h 48m1 stop

4:03 pm - 1:13 pmPNS-ORD

21h 10m2 stops

$223Spirit Airlines

Find Deal

vie., ene. 9 - lun., ene. 12

10:55 am - 1:31 pmORD-PNS

2h 36mnonstop

6:35 am - 1:00 pmPNS-ORD

6h 25m1 stop

$224United Airlines

Find Deal

vie., ene. 2 - mar., ene. 6

10:45 am - 1:32 pmORD-PNS

2h 47mnonstop

2:13 pm - 4:59 pmPNS-ORD

2h 46mnonstop

$225United Airlines

Find Deal

mié., ene. 7 - mar., ene. 13

12:46 pm - 6:42 pmMDW-PNS

5h 56m1 stop

1:37 pm - 5:45 pmPNS-MDW

4h 08m1 stop

$229Delta

Find Deal

mié., feb. 18 - lun., feb. 23

6:00 am - 1:05 pmMDW-PNS

7h 05m1 stop

5:00 pm - 10:42 pmPNS-MDW

5h 42m1 stop

$230Delta

Find Deal

sáb., feb. 14 - sáb., feb. 21

Southwest flights from Chicago to Pensacola

Our best Southwest deals on Chicago to Pensacola flight tickets

Southwest

Jan 29

ORD1:45 pmChicago O'Hare Intl

4h 40m

1 stop

PNS6:25 pmPensacola

Feb 2

PNS7:50 amPensacola

14h 00m

2 stops

ORD9:50 pmChicago O'Hare Intl

$214

Find similar

Southwest

Jan 31

MDW6:40 amChicago Midway

10h 25m

2 stops

PNS5:05 pmPensacola

Feb 7

PNS7:45 amPensacola

9h 10m

2 stops

MDW4:55 pmChicago Midway

$220

Find similar

Southwest

Feb 7

MDW6:00 amChicago Midway

3h 50m

1 stop

PNS9:50 amPensacola

Feb 13

PNS5:45 pmPensacola

3h 55m

1 stop

MDW9:40 pmChicago Midway

$222

Find similar

Delta flights from Chicago to Pensacola

Our best Delta deals on Chicago to Pensacola flight tickets

Delta

Apr 11

MDW4:30 pmChicago Midway

6h 37m

1 stop

PNS11:07 pmPensacola

Apr 18

PNS3:35 pmPensacola

6h 10m

1 stop

MDW9:45 pmChicago Midway

$229

Find similar

Delta

Jan 10

MDW6:45 amChicago Midway

4h 54m

1 stop

PNS11:39 amPensacola

Jan 20

PNS1:40 pmPensacola

3h 49m

1 stop

MDW5:29 pmChicago Midway

$238

Find similar

Delta

Jan 1

MDW6:00 amChicago Midway

4h 20m

1 stop

PNS10:20 amPensacola

Jan 8

PNS5:54 pmPensacola

4h 13m

1 stop

MDW10:07 pmChicago Midway

$248

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

jue. 1/29

1:45 pm-6:25 pm

1 stop4h 40m

Pensacola

lun. 2/2

7:50 am-9:50 pm

2 stops14h 00m

$214

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 12/16

10:00 am-1:13 pm

2 stops27h 13m

Pensacola

lun. 12/22

7:09 pm-3:42 pm

1 stop20h 33m

$215

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

jue. 12/11

6:15 am-6:14 pm

1 stop11h 59m

Pensacola

sáb. 12/13

4:44 pm-11:28 am

1 stop18h 44m

$218

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 2/17

8:10 am-3:26 pm

1 stop7h 16m

Pensacola

vie. 2/20

1:16 pm-3:57 pm

Nonstop2h 41m

$221

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mié. 12/10

7:10 am-1:13 pm

1 stop6h 03m

Pensacola

mar. 12/16

2:08 pm-12:09 am

1 stop10h 01m

$222

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

vie. 1/9

7:20 am-3:08 pm

1 stop7h 48m

Pensacola

lun. 1/12

4:03 pm-1:13 pm

2 stops21h 10m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

vie. 1/2

10:55 am-1:31 pm

Nonstop2h 36m

Pensacola

mar. 1/6

6:35 am-1:00 pm

1 stop6h 25m

$224

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mié. 1/7

10:45 am-1:32 pm

Nonstop2h 47m

Pensacola

mar. 1/13

2:13 pm-4:59 pm

Nonstop2h 46m

$225

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mié. 2/18

12:46 pm-6:42 pm

1 stop5h 56m

Pensacola

lun. 2/23

1:37 pm-5:45 pm

1 stop4h 08m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

sáb. 2/14

6:00 am-1:05 pm

1 stop7h 05m

Pensacola

sáb. 2/21

5:00 pm-10:42 pm

1 stop5h 42m

$230

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How to get the cheapest flight ticket from Chicago 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

Layovers

Other information

What is the typical price of a round-trip flight between Chicago and Pensacola?

What is the cheapest month to fly to Pensacola?

The cheapest month to fly to Pensacola from Chicago is in September. Flight prices, which tend to average around $268, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Pensacola from Chicago during January instead. Flights to Pensacola in January, while not as cheap as those in September, still average around $293.

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

On average, the least expensive day to fly to Pensacola from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $315. 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 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 $787. 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 to Pensacola flight route?

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

How far in advance should I book a flight to Pensacola?

You are more likely to see cheaper flights to Pensacola from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Pensacola for around $335 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pensacola from Chicago for as low as $299 on momondo.

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

There are 4 cabin classes available to choose from on Chicago 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 to Pensacola flights?

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

How have Chicago to Pensacola flight prices changed over time?

As of December 2025, prices for Chicago to Pensacola flights are approximately 86% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Pensacola

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

Estimated round-trip price

Cheap Chicago to Pensacola (CHI to PNS) flight deals and tips

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

Best Price Found	$238
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Pensacola	1 airport

The best one-way flight to Pensacola from Chicago in the past 72 hours is $238. The best round-trip flight deal from Chicago to Pensacola found on momondo in the last 72 hours is $277.

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

Direct flights go from Chicago to Pensacola every day.

There is 1 airport near Pensacola: Pensacola (PNS)

Search flight deals

How far is Chicago to Pensacola by plane?
The distance between Chicago and Pensacola is about 791.2 mi. A reasonable flight in good conditions will take 2h 20m.
When did momondo last update prices for flights from Chicago to Pensacola Airport?
Prices for flights from Chicago to Pensacola Airport refresh daily.
How many operators does momondo search for flights from Chicago to Pensacola Airport?
As of December 2025, there are 5 operators available to choose from for flights from Chicago to Pensacola Airport.
How old do you have to be to fly from Chicago to Pensacola Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Pensacola Airport.
What documentation or ID do you need to fly to Pensacola Airport?
The travel and health documents required for your trip to Pensacola Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Pensacola Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Pensacola?
Based on momondo bookings for flights between Chicago and Pensacola, the leading plane model is Boeing 737-800, making up 34.47% of the total bookings. Other popular models include Embraer 175 with 31.46%, Boeing 737-700 with 12.63%, and Boeing 737 MAX 8 with 4.81%.
What is the most popular airline from Chicago to Pensacola?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Pensacola is United Airlines (41% of total bookings). The next most popular airlines are Southwest (25%), American Airlines (15%), and Delta (10%).

Best airlines flying from Chicago to Pensacola

Compare and see reviews for airlines that fly from Chicago to Pensacola with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $118	Free Cancellation	Rating 6.3 8,161 reviews	Search Spirit Airlines flights
Delta	PriceFrom $177	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
United Airlines	PriceFrom $213	Free Cancellation	Rating 7.4 9,065 reviews	Search United Airlines flights
Southwest	PriceFrom $216	Free Cancellation	Rating 8.0 4,254 reviews	Search Southwest flights
American Airlines	PriceFrom $218	Free Cancellation	Rating 7.2 11,044 reviews	Search American Airlines flights

Southwest Flights From Chicago to Pensacola
Southwest is one of the most popular airlines flying from Chicago to Pensacola, operating 5 flights/week on average for this route. A good Southwest flight deal for Chicago to Pensacola starts from $216 round-trip, up to an average price of $369. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Chicago to Pensacola
Across 9,063 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to Pensacola about 6 times each week, with ticket deals ranging from $213 to $372. Price data is based on momondo searches in the last 72 hours.

Orange Beach

Pensacola Beach

Foley

Perdido Key

Navarre Beach

Navarre

Atmore

Milton

Gulf Breeze

Evergreen

Warrington

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Pensacola. Millions of users trust and use momondo every year so you are in good hands.

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?

momondo helps you find the best flight between Chicago and Pensacola by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Pensacola, momondo offers a useful price alert feature which will track prices for flights to Pensacola from Chicago and alert you when they 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.

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Cheap flights from Chicago to Pensacola from $70

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Pensacola departing on 1/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Chicago 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 typical price of a round-trip flight between Chicago and Pensacola?

What is the cheapest month to fly 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 to Pensacola flight route?

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

How far in advance should I book a flight to Pensacola?

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

There are 4 cabin classes available to choose from on Chicago 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 to Pensacola flights?

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

How have Chicago to Pensacola flight prices changed over time?

As of December 2025, prices for Chicago to Pensacola flights are approximately 86% more expensive when compared to flights at the same time last year.

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

Delta is the most popular carrier operating from Chicago to Pensacola

What airlines fly to Pensacola?

Which airport is the most popular layover for flights between Chicago and Pensacola?

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Pensacola?

Flights via Denver (DEN) offer the lowest average round-trip price of $170.

Which layover airport has the shortest travel time from Chicago to Pensacola?

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 4h 25m.

Which layover airport has the shortest connection time from Chicago to Pensacola?

Charlotte (CLT) has the shortest average layover time for this route: 0h 51m.

How many flights depart from Chicago to Pensacola on average per day?

The number of flights available between Chicago and Pensacola is 2 per day as of December 2025. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

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

As of December 2025, there are 19 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

When to book flights from Chicago to Pensacola

Cheap Chicago to Pensacola (CHI to PNS) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Pensacola

How far is Chicago to Pensacola by plane?

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

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

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

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

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

What is the most popular airline from Chicago to Pensacola?

Best airlines flying from Chicago to Pensacola

Compare and see reviews for airlines that fly from Chicago to Pensacola with momondo

Southwest Flights From Chicago to Pensacola

United Airlines Flights From Chicago 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.