What airlines fly to Chicago?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Pensacola according to our data. United Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Charlotte (CLT) has the shortest average layover time for this route: 0h 52m.

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

As of November 2025, 32 flights take off from Pensacola and land in Chicago each week. The most common flight departure day for this route is Fri, with 25% of weekly flights taking off on this day.

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

Charlotte (CLT) was the most common stop: 38% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Orlando (MCO) offer the lowest average round-trip price of $158.

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

Spirit Airlines, Southwest, and Delta are the most popular carriers operating from Pensacola to Chicago

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

Flights connecting via St. Louis (STL) have the shortest average one-way travel time: 4h 20m.

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

As of November 2025, 4 flights take off from Pensacola and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 97% of daily flights taking off in the afternoon.

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

Prices for flights from Pensacola Airport to Chicago were last updated today.

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

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

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

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 Pensacola Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago 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.

$81 Cheap Flights from Pensacola to Chicago in 2025/26

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Find the cheapest flights from Pensacola to Chicago

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Cheap round-trip flights

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2:39 pm - 5:10 pmPNS-ORD

2h 31mnonstop

10:50 am - 1:16 pmORD-PNS

2h 26mnonstop

$209United Airlines

Find Deal

sáb., dic. 13 - mié., dic. 17

4:15 pm - 10:35 pmPNS-MDW

6h 20m1 stop

10:50 am - 3:35 pmMDW-PNS

4h 45m1 stop

$212Southwest

Find Deal

mar., dic. 9 - mié., dic. 10

4:03 pm - 11:46 pmPNS-ORD

7h 43m1 stop

7:29 am - 3:08 pmORD-PNS

7h 39m1 stop

$213Spirit Airlines

Find Deal

vie., ene. 16 - lun., ene. 19

8:16 pm - 11:08 amPNS-ORD

14h 52m1 stop

7:00 am - 7:14 pmORD-PNS

36h 14m2 stops

$214Multiple Airlines

Find Deal

mié., dic. 3 - dom., dic. 7

1:16 pm - 3:55 pmPNS-ORD

2h 39mnonstop

8:25 am - 10:47 amORD-PNS

2h 22mnonstop

$215American Airlines

Find Deal

sáb., feb. 14 - mié., feb. 18

7:50 am - 2:05 pmPNS-MDW

6h 15m1 stop

10:50 am - 3:35 pmMDW-PNS

4h 45m1 stop

$218Southwest

Find Deal

sáb., dic. 13 - mié., dic. 17

7:09 pm - 11:14 amPNS-ORD

16h 05m1 stop

7:20 am - 6:14 pmORD-PNS

10h 54m1 stop

$219Multiple Airlines

Find Deal

jue., dic. 18 - jue., ene. 1

7:09 pm - 3:47 pmPNS-ORD

20h 38m2 stops

7:10 am - 6:14 pmORD-PNS

11h 04m1 stop

$222Spirit Airlines

Find Deal

vie., dic. 12 - dom., dic. 14

1:40 pm - 7:21 pmPNS-ORD

5h 41m1 stop

5:59 pm - 11:13 pmORD-PNS

5h 14m1 stop

$223Delta

Find Deal

mié., ene. 28 - sáb., ene. 31

5:54 pm - 10:07 pmPNS-MDW

4h 13m1 stop

6:00 am - 10:26 amMDW-PNS

4h 26m1 stop

$229Delta

Find Deal

vie., ene. 16 - lun., ene. 19

United Airlines flights from Pensacola to Chicago

Our best United Airlines deals on Pensacola to Chicago flight tickets

United Airlines

Dec 13

PNS2:39 pmPensacola

2h 31m

ORD5:10 pmChicago O'Hare Intl

Dec 17

ORD10:50 amChicago O'Hare Intl

2h 26m

PNS1:16 pmPensacola

$209

Find similar

United Airlines

Dec 2

PNS2:15 pmPensacola

2h 32m

ORD4:47 pmChicago O'Hare Intl

Jan 14

ORD10:45 amChicago O'Hare Intl

2h 47m

PNS1:32 pmPensacola

$308

Find similar

United Airlines

Nov 25

PNS2:17 pmPensacola

2h 31m

ORD4:48 pmChicago O'Hare Intl

Nov 28

ORD10:49 amChicago O'Hare Intl

2h 26m

PNS1:15 pmPensacola

$319

Find similar

Spirit Airlines flights from Pensacola to Chicago

Our best Spirit Airlines deals on Pensacola to Chicago flight tickets

Spirit Airlines

Jan 16

PNS4:03 pmPensacola

7h 43m

1 stop

ORD11:46 pmChicago O'Hare Intl

Jan 19

ORD7:29 amChicago O'Hare Intl

7h 39m

1 stop

PNS3:08 pmPensacola

$213

Find similar

Spirit Airlines

Dec 12

PNS7:09 pmPensacola

20h 38m

2 stops

ORD3:47 pmChicago O'Hare Intl

Dec 14

ORD7:10 amChicago O'Hare Intl

11h 04m

1 stop

PNS6:14 pmPensacola

$222

Find similar

Spirit Airlines

Nov 24

PNS5:54 pmPensacola

5h 12m

1 stop

ORD11:06 pmChicago O'Hare Intl

Dec 2

ORD10:12 amChicago O'Hare Intl

8h 59m

1 stop

PNS7:11 pmPensacola

$223

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

sáb. 12/13

2:39 pm-5:10 pm

Nonstop2h 31m

Chicago O'Hare Intl

mié. 12/17

10:50 am-1:16 pm

Nonstop2h 26m

$209

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

mar. 12/9

4:15 pm-10:35 pm

1 stop6h 20m

Chicago Midway

mié. 12/10

10:50 am-3:35 pm

1 stop4h 45m

$212

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

vie. 1/16

4:03 pm-11:46 pm

1 stop7h 43m

Chicago O'Hare Intl

lun. 1/19

7:29 am-3:08 pm

1 stop7h 39m

$213

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

mié. 12/3

8:16 pm-11:08 am

1 stop14h 52m

Chicago O'Hare Intl

dom. 12/7

7:00 am-7:14 pm

2 stops36h 14m

$214

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

sáb. 2/14

1:16 pm-3:55 pm

Nonstop2h 39m

Chicago O'Hare Intl

mié. 2/18

8:25 am-10:47 am

Nonstop2h 22m

$215

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

sáb. 12/13

7:50 am-2:05 pm

1 stop6h 15m

Chicago Midway

mié. 12/17

10:50 am-3:35 pm

1 stop4h 45m

$218

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

jue. 12/18

7:09 pm-11:14 am

1 stop16h 05m

Chicago O'Hare Intl

jue. 1/1

7:20 am-6:14 pm

1 stop10h 54m

$219

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

vie. 12/12

7:09 pm-3:47 pm

2 stops20h 38m

Chicago O'Hare Intl

dom. 12/14

7:10 am-6:14 pm

1 stop11h 04m

$222

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

mié. 1/28

1:40 pm-7:21 pm

1 stop5h 41m

Chicago O'Hare Intl

sáb. 1/31

5:59 pm-11:13 pm

1 stop5h 14m

$223

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

vie. 1/16

5:54 pm-10:07 pm

1 stop4h 13m

Chicago Midway

lun. 1/19

6:00 am-10:26 am

1 stop4h 26m

$229

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 Pensacola to Chicago

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 Pensacola and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Pensacola, with most prices found around $279. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Pensacola to Chicago during November average around $279.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $367. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Pensacola to Chicago for around $544.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pensacola to Chicago during this time can be as low as $307. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $440.

What is the cheapest Pensacola to Chicago flight route?

Fly from Pensacola to Chicago O'Hare Intl for the best Pensacola - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Pensacola when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $310 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Pensacola for as low as $196 on momondo.

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

There are 4 cabin classes available to choose from on Pensacola to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Pensacola to Chicago flight prices changed over time?

As of November 2025, prices for Pensacola to Chicago flights are approximately 11% cheaper when compared to flights at the same time last year.

When to book flights from Pensacola to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$139
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Pensacola in the past 72 hours is $139. The best round-trip flight deal from Pensacola to Chicago found on momondo in the last 72 hours is $253.

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

Direct flights go from Pensacola to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Pensacola to Chicago by plane?
A flight from Pensacola to Chicago will travel around 791.2 mi. 2h 31m is a normal flight duration for this route.
When did momondo last update prices for flights from Pensacola Airport to Chicago?
Prices for flights from Pensacola Airport to Chicago were last updated today.
How many operators does momondo search for flights from Pensacola Airport to Chicago?
As of November 2025, there are 5 operators available to choose from for flights from Pensacola Airport to Chicago.
How old do you have to be to fly from Pensacola Airport to Chicago?
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 Pensacola Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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 Pensacola to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Pensacola to Chicago is Boeing 737-800, representing 34.11% of all bookings. The subsequent popular models are Embraer 175 at 26.74%, Boeing 737-700 at 13.95%, and Boeing 737 MAX 8 at 6.20%.
What is the most popular airline from Pensacola to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Pensacola to Chicago is United Airlines (41% of total bookings). The next most popular airlines are Southwest (24%), Delta (17%), and American Airlines (15%).

Best airlines flying from Pensacola to Chicago

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $155	Free Cancellation	Rating 6.3 8,151 reviews	Search Spirit Airlines flights
Southwest	PriceFrom $173	Free Cancellation	Rating 8.0 4,248 reviews	Search Southwest flights
Delta	PriceFrom $194	Free Cancellation	Rating 7.9 8,003 reviews	Search Delta flights
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 9,019 reviews	Search United Airlines flights
American Airlines	PriceFrom $228	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights

United Airlines Flights From Pensacola to Chicago
United Airlines is one of the most popular airlines flying from Pensacola to Chicago, operating 8 flights/week on average for this route. A good United Airlines flight deal for Pensacola to Chicago starts from $209 round-trip, up to an average price of $343. Our users have rated United Airlines at 7.4/10.
American Airlines Flights From Pensacola to Chicago
$228 is the best American Airlines flight deal from Pensacola to Chicago found on momondo over the last 72 hours. The average American Airlines ticket price found was closer to $307, however, with flight time and availability significantly affecting the price. American Airlines (7.2/10 from 11,045 user reviews) flies into Chicago from Pensacola 4 times in an average week so prices can vary.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Pensacola.

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

momondo does allow users to show only those flights to Chicago from Pensacola which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Pensacola and Chicago 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 Pensacola to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Pensacola to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago 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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jue. 12/18

jue. 12/25

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Cheap flights from Pensacola to Chicago from $81

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Chicago departing on 12/16. 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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United Airlines flights from Pensacola to Chicago

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How to get the cheapest flight ticket from Pensacola to Chicago

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 Pensacola and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Pensacola, with most prices found around $279. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Pensacola to Chicago during November average around $279.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pensacola to Chicago during this time can be as low as $307. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $440.

What is the cheapest Pensacola to Chicago flight route?

Fly from Pensacola to Chicago O'Hare Intl for the best Pensacola - Chicago flight prices

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

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

There are 4 cabin classes available to choose from on Pensacola to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Pensacola to Chicago flight prices changed over time?

As of November 2025, prices for Pensacola to Chicago flights are approximately 11% cheaper when compared to flights at the same time last year.

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

Spirit Airlines, Southwest, and Delta are the most popular carriers operating from Pensacola to Chicago

What airlines fly to Chicago?

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

Charlotte (CLT) was the most common stop: 38% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Orlando (MCO) offer the lowest average round-trip price of $158.

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

Flights connecting via St. Louis (STL) have the shortest average one-way travel time: 4h 20m.

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

Charlotte (CLT) has the shortest average layover time for this route: 0h 52m.

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

As of November 2025, 4 flights take off from Pensacola and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 97% of daily flights taking off in the afternoon.

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

As of November 2025, 32 flights take off from Pensacola and land in Chicago each week. The most common flight departure day for this route is Fri, with 25% of weekly flights taking off on this day.

When to book flights from Pensacola to Chicago

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Pensacola to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

What is the most popular airline from Pensacola to Chicago?

Best airlines flying from Pensacola to Chicago

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

United Airlines Flights From Pensacola to Chicago

American Airlines Flights From Pensacola to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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.