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 airlines fly to Chicago?

United Airlines, Delta and American Airlines 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 33% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Charlotte (CLT) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

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

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

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

As of August 2025, 23 flights take off from Pensacola and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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.

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

Flights connecting via Nashville (BNA) have the shortest average one-way travel time: 3h 50m.

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

As of August 2025, 3 flights take off from Pensacola and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 100% 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 August 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.

$79 Cheap Flights from Pensacola to Chicago in 2025

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Find the cheapest flights from Pensacola to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

4:44 pm - 10:48 pmPNS-ORD

6h 04m1 stop

5:05 am - 3:39 pmORD-PNS

10h 34m1 stop

$173Spirit Airlines

Find Deal

Sat, Sep 20 - Sat, Oct 4

4:44 pm - 10:48 pmPNS-ORD

6h 04m1 stop

5:05 am - 3:39 pmORD-PNS

10h 34m1 stop

$181Spirit Airlines

Find Deal

Fri, Sep 19 - Sun, Sep 21

2:17 pm - 4:54 pmPNS-ORD

2h 37mnonstop

10:50 am - 1:15 pmORD-PNS

2h 25mnonstop

$203United Airlines

Find Deal

Fri, Oct 3 - Wed, Oct 8

2:17 pm - 4:54 pmPNS-ORD

2h 37mnonstop

10:50 am - 1:15 pmORD-PNS

2h 25mnonstop

$209United Airlines

Find Deal

Thu, Sep 25 - Mon, Sep 29

6:09 pm - 10:14 pmPNS-MDW

4h 05m1 stop

6:00 am - 10:42 amMDW-PNS

4h 42m1 stop

$223Delta

Find Deal

Fri, Oct 24 - Wed, Oct 29

4:03 pm - 8:23 pmPNS-ORD

4h 20m1 stop

6:00 am - 12:04 pmORD-PNS

6h 04m1 stop

$223Delta

Find Deal

Fri, Oct 24 - Wed, Oct 29

10:43 am - 5:13 pmPNS-ORD

6h 30m1 stop

10:30 am - 1:00 pmORD-PNS

2h 30mnonstop

$224American Airlines

Find Deal

Fri, Oct 31 - Tue, Nov 4

2:30 pm - 6:10 pmPNS-MDW

3h 40m1 stop

9:40 am - 5:30 pmMDW-PNS

7h 50m1 stop

$228Southwest

Find Deal

Wed, Oct 15 - Mon, Oct 20

11:05 am - 6:05 pmPNS-MDW

7h 00m1 stop

5:45 am - 11:45 amMDW-PNS

6h 00m1 stop

$229Southwest

Find Deal

Thu, Sep 25 - Mon, Sep 29

3:41 pm - 11:37 pmPNS-ORD

7h 56m1 stop

9:59 am - 12:30 pmORD-PNS

2h 31mnonstop

$230American Airlines

Find Deal

Fri, Nov 14 - Mon, Nov 17

American Airlines flights from Pensacola to Chicago

Our best American Airlines deals on Pensacola to Chicago flight tickets

American Airlines

Oct 31

PNS10:43 amPensacola

6h 30m

1 stop

ORD5:13 pmChicago O'Hare Intl

Nov 4

ORD10:30 amChicago O'Hare Intl

2h 30m

PNS1:00 pmPensacola

$224

Find similar

American Airlines

Nov 14

PNS3:41 pmPensacola

7h 56m

1 stop

ORD11:37 pmChicago O'Hare Intl

Nov 17

ORD9:59 amChicago O'Hare Intl

2h 31m

PNS12:30 pmPensacola

$230

Find similar

American Airlines

Dec 25

PNS1:12 pmPensacola

2h 42m

ORD3:54 pmChicago O'Hare Intl

Jan 1

ORD10:13 amChicago O'Hare Intl

2h 25m

PNS12:38 pmPensacola

$234

Find similar

United Airlines flights from Pensacola to Chicago

Our best United Airlines deals on Pensacola to Chicago flight tickets

United Airlines

Oct 3

PNS2:17 pmPensacola

2h 37m

ORD4:54 pmChicago O'Hare Intl

Oct 8

ORD10:50 amChicago O'Hare Intl

2h 25m

PNS1:15 pmPensacola

$203

Find similar

United Airlines

Sep 25

PNS2:17 pmPensacola

2h 37m

ORD4:54 pmChicago O'Hare Intl

Sep 29

ORD10:50 amChicago O'Hare Intl

2h 25m

PNS1:15 pmPensacola

$209

Find similar

United Airlines

Oct 15

PNS2:17 pmPensacola

2h 37m

ORD4:54 pmChicago O'Hare Intl

Oct 20

ORD10:50 amChicago O'Hare Intl

2h 25m

PNS1:15 pmPensacola

$227

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 9/20

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Sat 10/4

5:05 am-3:39 pm

1 stop10h 34m

$173

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 9/19

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Sun 9/21

5:05 am-3:39 pm

1 stop10h 34m

$181

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 10/3

2:17 pm-4:54 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 10/8

10:50 am-1:15 pm

Nonstop2h 25m

$203

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 9/25

2:17 pm-4:54 pm

Nonstop2h 37m

Chicago O'Hare Intl

Mon 9/29

10:50 am-1:15 pm

Nonstop2h 25m

$209

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/24

6:09 pm-10:14 pm

1 stop4h 05m

Chicago Midway

Wed 10/29

6:00 am-10:42 am

1 stop4h 42m

$223

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 10/24

4:03 pm-8:23 pm

1 stop4h 20m

Chicago O'Hare Intl

Wed 10/29

6:00 am-12:04 pm

1 stop6h 04m

$223

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 10/31

10:43 am-5:13 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 11/4

10:30 am-1:00 pm

Nonstop2h 30m

$224

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 10/15

2:30 pm-6:10 pm

1 stop3h 40m

Chicago Midway

Mon 10/20

9:40 am-5:30 pm

1 stop7h 50m

$228

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 9/25

11:05 am-6:05 pm

1 stop7h 00m

Chicago Midway

Mon 9/29

5:45 am-11:45 am

1 stop6h 00m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 11/14

3:41 pm-11:37 pm

1 stop7h 56m

Chicago O'Hare Intl

Mon 11/17

9:59 am-12:30 pm

Nonstop2h 31m

$230

Flights are sorted by cheapest round-trip flights first.

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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

Prices

Airlines

Layovers

Other information

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 $288.

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 $400. 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 $686.

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 $505.

What is the cheapest Pensacola to Chicago flight route?

Fly from Pensacola to Chicago Midway 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 $326 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.

Can stopping save me money on Pensacola to Chicago flights?

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

How have Pensacola to Chicago flight prices changed over time?

As of August 2025, prices for Pensacola to Chicago flights are approximately 7% 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	$199
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Pensacola in the past 72 hours is $199. The best round-trip flight deal from Pensacola to Chicago found on momondo in the last 72 hours is $287.

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

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 10m 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 August 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 Airbus A319, representing 30.00% of all bookings. The subsequent popular models are Boeing 737-700 at 14.21%, Airbus A320-100/200 at 12.11%, and Boeing 737-800 at 8.95%.
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 (38% of total bookings). The next most popular airlines are Southwest (23%), Delta (19%), and American Airlines (14%).

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 8,030 reviews	Search Spirit Airlines flights
Southwest	PriceFrom $173	Free Cancellation	Rating 8.0 4,241 reviews	Search Southwest flights
Delta	PriceFrom $194	Free Cancellation	Rating 7.9 7,977 reviews	Search Delta flights
United Airlines	PriceFrom $213	Free Cancellation	Rating 7.4 8,945 reviews	Search United Airlines flights
American Airlines	PriceFrom $228	Free Cancellation	Rating 7.2 10,000 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 5 flights/week on average for this route. A good United Airlines flight deal for Pensacola to Chicago starts from $213 round-trip, up to an average price of $393. Our users have rated United Airlines at 7.4/10.

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New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Dallasfrom $45

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Flights to Denverfrom $37

Cheap flights from Pensacola to Chicago from $79

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 9/16. 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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American Airlines flights from Pensacola to Chicago

Our best American Airlines deals on Pensacola to Chicago flight tickets

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Our best United Airlines deals on Pensacola to Chicago flight tickets

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

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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 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 $288.

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 $505.

What is the cheapest Pensacola to Chicago flight route?

Fly from Pensacola to Chicago Midway 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.

Can stopping save me money on Pensacola to Chicago flights?

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

How have Pensacola to Chicago flight prices changed over time?

As of August 2025, prices for Pensacola to Chicago flights are approximately 7% cheaper when compared to flights at the same time last year.

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

Spirit Airlines, United Airlines, and Southwest 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: 43% 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 Nashville (BNA) have the shortest average one-way travel time: 3h 50m.

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 August 2025, 3 flights take off from Pensacola and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 100% of daily flights taking off in the afternoon.

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

As of August 2025, 23 flights take off from Pensacola and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% 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

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.