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

Southwest, United Airlines, and Frontier are the most popular carriers operating from Chicago to Pensacola

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

The number of flights available between Chicago and Pensacola is 1 per day as of September 2025. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

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 41% 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 connection time from Chicago to Pensacola?

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

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

Atlanta (ATL) was the most common stop: 53% 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 Atlanta (ATL) have the shortest average one-way travel time: 4h 08m.

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

As of September 2025, there are 12 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.

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 September 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.

$66 Cheap Flights from Chicago to Pensacola in 2025

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

Prices are currently low for flights on this route. Typical prices usually range from $233 to $412. The lowest price recently found on this route was $204.

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Find the cheapest flights from Chicago to Pensacola

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:40 am - 9:15 amMDW-PNS

3h 35m1 stop

7:35 am - 3:00 pmPNS-MDW

7h 25m2 stops

$204Southwest

Find Deal

Mon, Sep 29 - Wed, Oct 1

5:45 am - 11:10 amMDW-PNS

5h 25m1 stop

2:30 pm - 6:10 pmPNS-MDW

3h 40m1 stop

$205Southwest

Find Deal

Sat, Oct 4 - Wed, Oct 8

5:05 am - 3:31 pmORD-PNS

10h 26m1 stop

4:36 pm - 11:45 pmPNS-ORD

7h 09m1 stop

$206Spirit Airlines

Find Deal

Fri, Oct 10 - Fri, Oct 17

12:05 pm - 6:10 pmORD-PNS

6h 05m1 stop

4:44 pm - 10:48 pmPNS-ORD

6h 04m1 stop

$207Spirit Airlines

Find Deal

Thu, Sep 25 - Tue, Sep 30

5:20 am - 10:39 amORD-PNS

5h 19m1 stop

7:00 am - 12:17 pmPNS-ORD

5h 17m1 stop

$211Delta

Find Deal

Sun, Oct 26 - Sat, Nov 8

10:50 am - 1:15 pmORD-PNS

2h 25mnonstop

2:17 pm - 4:54 pmPNS-ORD

2h 37mnonstop

$215United Airlines

Find Deal

Wed, Oct 22 - Sat, Oct 25

6:45 am - 10:39 amORD-PNS

3h 54m1 stop

12:44 pm - 7:25 pmPNS-ORD

6h 41m1 stop

$218Delta

Find Deal

Sat, Oct 18 - Wed, Oct 22

10:49 am - 1:15 pmORD-PNS

2h 26mnonstop

2:17 pm - 4:48 pmPNS-ORD

2h 31mnonstop

$219United Airlines

Find Deal

Mon, Oct 27 - Wed, Nov 12

10:30 am - 1:00 pmORD-PNS

2h 30mnonstop

5:14 pm - 11:57 pmPNS-ORD

6h 43m1 stop

$240American Airlines

Find Deal

Wed, Nov 5 - Wed, Nov 19

10:30 am - 1:00 pmORD-PNS

2h 30mnonstop

1:32 pm - 4:11 pmPNS-ORD

2h 39mnonstop

$244American Airlines

Find Deal

Wed, Nov 5 - Tue, Nov 11

American Airlines flights from Chicago to Pensacola

Our best American Airlines deals on Chicago to Pensacola flight tickets

American Airlines

Nov 5

ORD10:30 amChicago O'Hare Intl

2h 30m

PNS1:00 pmPensacola

Nov 19

PNS5:14 pmPensacola

6h 43m

1 stop

ORD11:57 pmChicago O'Hare Intl

$240

Find similar

American Airlines

Nov 5

ORD10:30 amChicago O'Hare Intl

2h 30m

PNS1:00 pmPensacola

Nov 11

PNS1:32 pmPensacola

2h 39m

ORD4:11 pmChicago O'Hare Intl

$244

Find similar

American Airlines

Nov 5

ORD4:40 pmChicago O'Hare Intl

6h 19m

1 stop

PNS10:59 pmPensacola

Nov 12

PNS1:32 pmPensacola

2h 39m

ORD4:11 pmChicago O'Hare Intl

$250

Find similar

Spirit Airlines flights from Chicago to Pensacola

Our best Spirit Airlines deals on Chicago to Pensacola flight tickets

Spirit Airlines

Oct 10

ORD5:05 amChicago O'Hare Intl

10h 26m

1 stop

PNS3:31 pmPensacola

Oct 17

PNS4:36 pmPensacola

7h 09m

1 stop

ORD11:45 pmChicago O'Hare Intl

$206

Find similar

Spirit Airlines

Sep 25

ORD12:05 pmChicago O'Hare Intl

6h 05m

1 stop

PNS6:10 pmPensacola

Sep 30

PNS4:44 pmPensacola

6h 04m

1 stop

ORD10:48 pmChicago O'Hare Intl

$207

Find similar

Spirit Airlines

Oct 8

ORD6:00 amChicago O'Hare Intl

11h 01m

1 stop

PNS5:01 pmPensacola

Oct 12

PNS4:36 pmPensacola

7h 09m

1 stop

ORD11:45 pmChicago O'Hare Intl

$208

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 9/29

5:40 am-9:15 am

1 stop3h 35m

Pensacola

Wed 10/1

7:35 am-3:00 pm

2 stops7h 25m

$204

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 10/4

5:45 am-11:10 am

1 stop5h 25m

Pensacola

Wed 10/8

2:30 pm-6:10 pm

1 stop3h 40m

$205

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 10/10

5:05 am-3:31 pm

1 stop10h 26m

Pensacola

Fri 10/17

4:36 pm-11:45 pm

1 stop7h 09m

$206

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 9/25

12:05 pm-6:10 pm

1 stop6h 05m

Pensacola

Tue 9/30

4:44 pm-10:48 pm

1 stop6h 04m

$207

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 10/26

5:20 am-10:39 am

1 stop5h 19m

Pensacola

Sat 11/8

7:00 am-12:17 pm

1 stop5h 17m

$211

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 10/22

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Sat 10/25

2:17 pm-4:54 pm

Nonstop2h 37m

$215

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 10/18

6:45 am-10:39 am

1 stop3h 54m

Pensacola

Wed 10/22

12:44 pm-7:25 pm

1 stop6h 41m

$218

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 10/27

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Wed 11/12

2:17 pm-4:48 pm

Nonstop2h 31m

$219

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 11/5

10:30 am-1:00 pm

Nonstop2h 30m

Pensacola

Wed 11/19

5:14 pm-11:57 pm

1 stop6h 43m

$240

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 11/5

10:30 am-1:00 pm

Nonstop2h 30m

Pensacola

Tue 11/11

1:32 pm-4:11 pm

Nonstop2h 39m

$244

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 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 January. Flight prices, which tend to average around $298, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Pensacola from Chicago during April instead. Flights to Pensacola in April, while not as cheap as those in January, still average around $306.

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 $319. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday 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 $419.

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

The cheapest time of day to fly to Pensacola is in the afternoon when flights can be purchased for as low as $293. Flights to Pensacola are more costly in the morning, with an average ticket price of $386. Departure times in the morning 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 O'Hare Intl 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 $355 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 $271 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.

How have Chicago to Pensacola flight prices changed over time?

As of September 2025, prices for Chicago to Pensacola flights are approximately 22% 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	$135
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Pensacola	1 airport

The best one-way flight to Pensacola from Chicago in the past 72 hours is $135. The best round-trip flight deal from Chicago to Pensacola found on momondo in the last 72 hours is $264.

The fastest flight from Chicago to Pensacola takes 2h 15m

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 25m.
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 September 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 Airbus A319, making up 28.73% of the total bookings. Other popular models include Boeing 737-700 with 18.42%, Boeing 737-800 with 17.98%, and Embraer 175 with 9.21%.
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 (44% of total bookings). The next most popular airlines are Southwest (22%), American Airlines (13%), and Delta (12%).

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 8,023 reviews	Search Spirit Airlines flights
Delta	PriceFrom $196	Free Cancellation	Rating 7.9 7,960 reviews	Search Delta flights
Southwest	PriceFrom $216	Free Cancellation	Rating 8.0 4,248 reviews	Search Southwest flights
American Airlines	PriceFrom $223	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.4 8,937 reviews	Search United Airlines flights

United Airlines Flights From Chicago to Pensacola
United Airlines is one of the most popular airlines flying from Chicago to Pensacola, operating 6 flights/week on average for this route. A good United Airlines flight deal for Chicago to Pensacola starts from $229 round-trip, up to an average price of $393. Our users have rated United Airlines at 7.4/10.

Orange Beach

Pensacola Beach

Foley

Perdido Key

Navarre Beach

Navarre

Atmore

Milton

Gulf Breeze

Warrington

Evergreen

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 $66

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 11/18. 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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American Airlines flights from Chicago to Pensacola

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Our best Spirit Airlines deals on Chicago to Pensacola flight tickets

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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 O'Hare Intl 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.

How have Chicago to Pensacola flight prices changed over time?

As of September 2025, prices for Chicago to Pensacola flights are approximately 22% more expensive when compared to flights at the same time last year.

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

Southwest, United Airlines, and Frontier are the most popular carriers 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: 53% 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 Atlanta (ATL) have the shortest average one-way travel time: 4h 08m.

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 1 per day as of September 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 September 2025, there are 12 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 17% 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

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.

Find better results for your trip to the United States

Airports servicing Florida