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

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

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

As of January 2026, 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 92% of daily flights taking off in the afternoon.

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

Charlotte (CLT) has the shortest average layover time for this route: 0h 53m.

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 37% 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.

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

As of January 2026, 34 flights take off from Pensacola and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.

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

Southwest, Spirit Airlines, 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 Atlanta (ATL) have the shortest average one-way travel time: 4h 12m.

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

Atlanta (ATL) was the most common stop: 40% of momondo users choosing 1-stop flights on this route connected there.

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 January 2026, 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.

$70 Cheap Flights from Pensacola to Chicago in 2026

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Find the cheapest flights from Pensacola to Chicago

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

1:15 pm - 4:00 pm

PNS

ORD

2h 45mnonstop

11:50 am - 2:13 pm

ORD

PNS

2h 23mnonstop

$155American Airlines

Tue, Mar 17 - Tue, Mar 24

4:03 pm - 11:46 pm

PNS

ORD

7h 43m1 stop

5:15 am - 3:08 pm

ORD

PNS

9h 53m1 stop

$162Spirit Airlines

Thu, Jan 22 - Sun, Jan 25

5:20 pm - 11:22 am

PNS

ORD

18h 02m1 stop

7:00 am - 3:54 pm

ORD

PNS

8h 54m1 stop

$166Spirit Airlines

Tue, Feb 17 - Sat, Feb 28

4:03 pm - 11:46 pm

PNS

ORD

7h 43m1 stop

10:48 am - 4:37 pm

ORD

PNS

5h 49m1 stop

$172Spirit Airlines

Fri, Jan 30 - Tue, Feb 3

6:00 am - 10:05 am

PNS

ORD

4h 05m1 stop

5:30 am - 12:35 pm

ORD

PNS

7h 05m1 stop

$177Delta

Wed, Feb 4 - Wed, Feb 11

6:37 pm - 2:55 pm

PNS

MDW

20h 18m1 stop

9:22 pm - 5:42 pm

MDW

PNS

20h 20m1 stop

$183Multiple Airlines

Fri, Feb 20 - Mon, Feb 23

7:05 am - 1:00 pm

PNS

MDW

5h 55m1 stop

8:15 am - 3:15 pm

MDW

PNS

7h 00m1 stop

$193Southwest

Thu, Feb 5 - Tue, Feb 10

6:00 am - 11:59 am

PNS

MDW

5h 59m1 stop

10:45 am - 3:09 pm

MDW

PNS

4h 24m1 stop

$194Delta

Thu, Mar 5 - Tue, Mar 10

5:33 pm - 7:52 pm

PNS

MDW

26h 19m1 stop

1:00 pm - 4:37 pm

MDW

PNS

27h 37m1 stop

$196Multiple Airlines

Thu, Jan 22 - Mon, Jan 26

7:05 am - 1:00 pm

PNS

MDW

5h 55m1 stop

6:10 am - 3:15 pm

MDW

PNS

9h 05m2 stops

$199Southwest

Thu, Feb 5 - Tue, Feb 10

Spirit Airlines flights from Pensacola to Chicago

Our best Spirit Airlines deals on Pensacola to Chicago flight tickets

Spirit Airlines

Jan 22

PNS4:03 pmPensacola

7h 43m

1 stop

ORD11:46 pmChicago O'Hare Intl

Jan 25

ORD5:15 amChicago O'Hare Intl

9h 53m

1 stop

PNS3:08 pmPensacola

$162

Spirit Airlines

Feb 17

PNS5:20 pmPensacola

18h 02m

1 stop

ORD11:22 amChicago O'Hare Intl

Feb 28

ORD7:00 amChicago O'Hare Intl

8h 54m

1 stop

PNS3:54 pmPensacola

$166

Spirit Airlines

Jan 30

PNS4:03 pmPensacola

7h 43m

1 stop

ORD11:46 pmChicago O'Hare Intl

Feb 3

ORD10:48 amChicago O'Hare Intl

5h 49m

1 stop

PNS4:37 pmPensacola

$172

Delta flights from Pensacola to Chicago

Our best Delta deals on Pensacola to Chicago flight tickets

Delta

Feb 4

PNS6:00 amPensacola

4h 05m

1 stop

ORD10:05 amChicago O'Hare Intl

Feb 11

ORD5:30 amChicago O'Hare Intl

7h 05m

1 stop

PNS12:35 pmPensacola

$177

Delta

Mar 5

PNS1:37 pmPensacola

5h 12m

1 stop

ORD6:49 pmChicago O'Hare Intl

Mar 10

ORD2:38 pmChicago O'Hare Intl

5h 51m

1 stop

PNS8:29 pmPensacola

$194

Delta

Mar 14

PNS9:15 amPensacola

4h 33m

1 stop

ORD1:48 pmChicago O'Hare Intl

Mar 18

ORD7:05 amChicago O'Hare Intl

4h 06m

1 stop

PNS11:11 amPensacola

$203

Fly from

Fly to

Route

Depart

Return

Price

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 3/17

1:15 pm-4:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 3/24

11:50 am-2:13 pm

Nonstop2h 23m

$155

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 1/22

4:03 pm-11:46 pm

1 stop7h 43m

Chicago O'Hare Intl

Sun 1/25

5:15 am-3:08 pm

1 stop9h 53m

$162

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 2/17

5:20 pm-11:22 am

1 stop18h 02m

Chicago O'Hare Intl

Sat 2/28

7:00 am-3:54 pm

1 stop8h 54m

$166

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 1/30

4:03 pm-11:46 pm

1 stop7h 43m

Chicago O'Hare Intl

Tue 2/3

10:48 am-4:37 pm

1 stop5h 49m

$172

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 2/4

6:00 am-10:05 am

1 stop4h 05m

Chicago O'Hare Intl

Wed 2/11

5:30 am-12:35 pm

1 stop7h 05m

$177

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 2/20

6:37 pm-2:55 pm

1 stop20h 18m

Chicago Midway

Mon 2/23

9:22 pm-5:42 pm

1 stop20h 20m

$183

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 2/5

7:05 am-1:00 pm

1 stop5h 55m

Chicago Midway

Tue 2/10

8:15 am-3:15 pm

1 stop7h 00m

$193

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/5

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Tue 3/10

10:45 am-3:09 pm

1 stop4h 24m

$194

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 1/22

5:33 pm-7:52 pm

1 stop26h 19m

Chicago Midway

Mon 1/26

1:00 pm-4:37 pm

1 stop27h 37m

$196

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 2/5

7:05 am-1:00 pm

1 stop5h 55m

Chicago Midway

Tue 2/10

6:10 am-3:15 pm

2 stops9h 05m

$199

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 November is, on average, the cheapest month to fly to Chicago from Pensacola, with most prices found around $273. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Pensacola to Chicago during February 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 $373. 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 $543.

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 afternoon. Flights from Pensacola to Chicago during this time can be as low as $348. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $432.

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 $309 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?

You could potentially save up to 8% on your flight if you consider stops on a Pensacola to Chicago flight.

How have Pensacola to Chicago flight prices changed over time?

As of January 2026, prices for Pensacola to Chicago flights are approximately 68% more expensive 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	$219
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Pensacola in the past 72 hours is $219. The best round-trip flight deal from Pensacola to Chicago found on momondo in the last 72 hours is $363.

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

Direct flights go from Pensacola to Chicago every day.

There are 3 airports in Chicago. From Pensacola there are direct flights to 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 15m 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 January 2026, 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 Embraer 175, representing 38.36% of all bookings. The subsequent popular models are Boeing 737-800 at 30.14%, Boeing 737 MAX 8 at 7.88%, and Airbus A319 at 6.51%.
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 (37% of total bookings). The next most popular airlines are Southwest (26%), American Airlines (17%), and Delta (16%).

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 8,287 reviews	Search Spirit Airlines flights
Delta	PriceFrom $196	Free Cancellation	Rating 7.9 8,025 reviews	Search Delta flights
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 9,139 reviews	Search United Airlines flights
Southwest	PriceFrom $216	Free Cancellation	Rating 8.0 4,248 reviews	Search Southwest flights
American Airlines	PriceFrom $229	Free Cancellation	Rating 7.2 11,095 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 13 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 $317. Our users have rated United Airlines at 7.4/10.

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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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Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Las Vegasfrom $55

Flights to Washington, D.C.from $58

Flights to Bostonfrom $58

Flights to Atlantafrom $48

Flights to Dallasfrom $57

Flights to Seattlefrom $57

Flights to Denverfrom $38

Cheap flights from Pensacola to Chicago 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 Pensacola to Chicago departing on 2/28. 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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Spirit Airlines flights from Pensacola to Chicago

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How to get the cheapest flight ticket from Pensacola to Chicago

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Pensacola, with most prices found around $273. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Pensacola to Chicago during February 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 afternoon. Flights from Pensacola to Chicago during this time can be as low as $348. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $432.

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.

Can stopping save me money on Pensacola to Chicago flights?

You could potentially save up to 8% on your flight if you consider stops on a Pensacola to Chicago flight.

How have Pensacola to Chicago flight prices changed over time?

As of January 2026, prices for Pensacola to Chicago flights are approximately 68% more expensive when compared to flights at the same time last year.

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

Southwest, Spirit Airlines, 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?

Atlanta (ATL) was the most common stop: 40% 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 Atlanta (ATL) have the shortest average one-way travel time: 4h 12m.

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

Charlotte (CLT) has the shortest average layover time for this route: 0h 53m.

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

As of January 2026, 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 92% of daily flights taking off in the afternoon.

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

As of January 2026, 34 flights take off from Pensacola and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% 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.

Find better results for your trip to the United States