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 travel time from Chicago to Pensacola?

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

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

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

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 week?

As of November 2025, there are 12 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 25% of flights taking off on this day.

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 1 per day as of November 2025. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

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

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

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 November 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.

$61 Cheap Flights from Chicago to Pensacola in 2025/26

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 $248 to $464. The lowest price recently found on this route was $209.

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 to Pensacola

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:25 am - 10:47 amORD-PNS

2h 22mnonstop

1:16 pm - 3:55 pmPNS-ORD

2h 39mnonstop

$209American Airlines

Find Deal

mié., feb. 18 - lun., feb. 23

6:48 am - 4:59 pmORD-PNS

10h 11m1 stop

8:16 pm - 9:17 amPNS-ORD

13h 01m1 stop

$212Spirit Airlines

Find Deal

mié., nov. 26 - mar., dic. 2

4:20 pm - 4:04 pmORD-PNS

23h 44m2 stops

4:44 pm - 1:08 pmPNS-ORD

20h 24m1 stop

$216Multiple Airlines

Find Deal

vie., dic. 5 - mié., dic. 10

10:52 am - 7:11 pmORD-PNS

8h 19m1 stop

5:15 pm - 12:15 amPNS-ORD

7h 00m1 stop

$217Multiple Airlines

Find Deal

vie., nov. 14 - lun., nov. 17

10:50 am - 1:17 pmORD-PNS

2h 27mnonstop

2:15 pm - 4:47 pmPNS-ORD

2h 32mnonstop

$228United Airlines

Find Deal

mié., dic. 3 - dom., dic. 7

10:49 am - 1:15 pmORD-PNS

2h 26mnonstop

2:17 pm - 4:48 pmPNS-ORD

2h 31mnonstop

$229United Airlines

Find Deal

jue., nov. 20 - lun., nov. 24

6:00 am - 12:32 pmMDW-PNS

6h 32m1 stop

5:42 pm - 10:44 pmPNS-MDW

5h 02m1 stop

$229Delta

Find Deal

mié., feb. 18 - lun., feb. 23

5:55 am - 11:20 amMDW-PNS

5h 25m1 stop

7:50 am - 4:45 pmPNS-MDW

8h 55m2 stops

$234Southwest

Find Deal

dom., feb. 1 - mar., feb. 3

6:00 am - 10:41 amMDW-PNS

4h 41m1 stop

7:09 pm - 11:40 pmPNS-MDW

4h 31m1 stop

$249Delta

Find Deal

jue., nov. 20 - lun., nov. 24

5:35 am - 9:20 amMDW-PNS

3h 45m1 stop

12:05 pm - 5:00 pmPNS-MDW

4h 55m1 stop

$269Southwest

Find Deal

jue., nov. 20 - mar., nov. 25

United Airlines flights from Chicago to Pensacola

Our best United Airlines deals on Chicago to Pensacola flight tickets

United Airlines

Dec 3

ORD10:50 amChicago O'Hare Intl

2h 27m

PNS1:17 pmPensacola

Dec 7

PNS2:15 pmPensacola

2h 32m

ORD4:47 pmChicago O'Hare Intl

$228

Find similar

United Airlines

Nov 20

ORD10:49 amChicago O'Hare Intl

2h 26m

PNS1:15 pmPensacola

Nov 24

PNS2:17 pmPensacola

2h 31m

ORD4:48 pmChicago O'Hare Intl

$229

Find similar

United Airlines

Jan 4

ORD10:55 amChicago O'Hare Intl

2h 36m

PNS1:31 pmPensacola

Jan 11

PNS6:35 amPensacola

6h 25m

1 stop

ORD1:00 pmChicago O'Hare Intl

$258

Find similar

Delta flights from Chicago to Pensacola

Our best Delta deals on Chicago to Pensacola flight tickets

Delta

Feb 18

MDW6:00 amChicago Midway

6h 32m

1 stop

PNS12:32 pmPensacola

Feb 23

PNS5:42 pmPensacola

5h 02m

1 stop

MDW10:44 pmChicago Midway

$229

Find similar

Delta

Nov 20

MDW6:00 amChicago Midway

4h 41m

1 stop

PNS10:41 amPensacola

Nov 24

PNS7:09 pmPensacola

4h 31m

1 stop

MDW11:40 pmChicago Midway

$249

Find similar

Delta

Dec 18

ORD5:30 amChicago O'Hare Intl

5h 10m

1 stop

PNS10:40 amPensacola

Dec 24

PNS5:31 pmPensacola

6h 31m

1 stop

ORD12:02 amChicago O'Hare Intl

$250

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mié. 2/18

8:25 am-10:47 am

Nonstop2h 22m

Pensacola

lun. 2/23

1:16 pm-3:55 pm

Nonstop2h 39m

$209

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mié. 11/26

6:48 am-4:59 pm

1 stop10h 11m

Pensacola

mar. 12/2

8:16 pm-9:17 am

1 stop13h 01m

$212

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

vie. 12/5

4:20 pm-4:04 pm

2 stops23h 44m

Pensacola

mié. 12/10

4:44 pm-1:08 pm

1 stop20h 24m

$216

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

vie. 11/14

10:52 am-7:11 pm

1 stop8h 19m

Pensacola

lun. 11/17

5:15 pm-12:15 am

1 stop7h 00m

$217

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mié. 12/3

10:50 am-1:17 pm

Nonstop2h 27m

Pensacola

dom. 12/7

2:15 pm-4:47 pm

Nonstop2h 32m

$228

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

jue. 11/20

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

lun. 11/24

2:17 pm-4:48 pm

Nonstop2h 31m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mié. 2/18

6:00 am-12:32 pm

1 stop6h 32m

Pensacola

lun. 2/23

5:42 pm-10:44 pm

1 stop5h 02m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

dom. 2/1

5:55 am-11:20 am

1 stop5h 25m

Pensacola

mar. 2/3

7:50 am-4:45 pm

2 stops8h 55m

$234

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

jue. 11/20

6:00 am-10:41 am

1 stop4h 41m

Pensacola

lun. 11/24

7:09 pm-11:40 pm

1 stop4h 31m

$249

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

jue. 11/20

5:35 am-9:20 am

1 stop3h 45m

Pensacola

mar. 11/25

12:05 pm-5:00 pm

1 stop4h 55m

$269

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 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 $298.

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 $309. 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 $399.

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 evening, with an average ticket price of $379. Departure times in the evening 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 $338 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 $302 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 November 2025, prices for Chicago to Pensacola flights are approximately 51% cheaper 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	$136
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 $136. The best round-trip flight deal from Chicago to Pensacola found on momondo in the last 72 hours is $236.

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 15m.
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 November 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 33.49% of the total bookings. Other popular models include Boeing 737-700 with 19.48%, Embraer 175 with 19.24%, and Airbus A319 with 9.03%.
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 (43% of total bookings). The next most popular airlines are Southwest (25%), American Airlines (14%), and Delta (11%).

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 8,115 reviews	Search Spirit Airlines flights
Delta	PriceFrom $177	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
Southwest	PriceFrom $216	Free Cancellation	Rating 8.0 4,238 reviews	Search Southwest flights
American Airlines	PriceFrom $217	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
United Airlines	PriceFrom $218	Free Cancellation	Rating 7.4 8,997 reviews	Search United Airlines flights

Southwest Flights From Chicago to Pensacola
Southwest is one of the most popular airlines flying from Chicago to Pensacola, operating 3 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 $388. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Chicago to Pensacola
Across 8,997 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to Pensacola about 4 times each week, with ticket deals ranging from $218 to $377. Price data is based on momondo searches in the last 72 hours.

Orange Beach

Pensacola Beach

Foley

Perdido Key

Navarre Beach

Navarre

Milton

Atmore

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

mié. 12/3

mié. 12/10

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 $49

Flights to Los Angelesfrom $49

Flights to Miamifrom $49

Flights to Chicagofrom $54

Flights to Orlandofrom $47

Flights to Las Vegasfrom $49

Flights to San Franciscofrom $54

Flights to Washington, D.C.from $54

Flights to Bostonfrom $40

Flights to Atlantafrom $40

Flights to Dallasfrom $49

Flights to Seattlefrom $68

Fly to other destinations from Chicago

Flights from Chicago Midway to Newark

Flights from Chicago O'Hare Intl to New York John F Kennedy Intl

Flights from Chicago O'Hare Intl to Minneapolis St Paul

Flights from Chicago O'Hare Intl to Nashville Intl

Flights from Chicago Midway to Asheville Regional

Flights from Chicago Midway to Atlanta Hartsfield-Jackson

Cheap flights from Chicago to Pensacola from $61

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 12/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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 to Pensacola

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

United Airlines flights from Chicago to Pensacola

Our best United Airlines deals on Chicago to Pensacola flight tickets

Delta flights from Chicago to Pensacola

Our best Delta deals on Chicago to Pensacola flight tickets

momondo Fare Finder

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

See travel insights to Pensacola from

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.

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 November 2025, prices for Chicago to Pensacola flights are approximately 51% cheaper when compared to flights at the same time last year.

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

Frontier, Spirit Airlines, and United Airlines 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: 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 1 per day as of November 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 November 2025, there are 12 flights per week flying from Chicago 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 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.