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$81+ Cheap flights from Pensacola (PNS) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
ene. 15 — ene. 221
jue. 1/15
jue. 1/22
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chicago are usually found in February or November, booked 37 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Pensacola to Chicago

Cheapest flights from Pensacola to Chicago
Explore the most affordable flight options available from Pensacola to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 16, 2025.

This Mytrip deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/301:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
lun. 1/55:00 amORD - PNS
1 stop13h 14mSpirit Airlines
Deal found 12/15$269
This American Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3011:29 amPNS - ORD
1 stop8h 08mAmerican Airlines
lun. 1/510:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Deal found 12/15$274
This Kiwi.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/311:58 pmPNS - ORD
2 stops28h 35mMultiple Airlines
lun. 1/55:00 amORD - PNS
1 stop13h 14mMultiple Airlines
Deal found 12/15$277
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/284:19 pmPNS - ORD
1 stop8h 24mAmerican Airlines
jue. 1/110:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Deal found 12/16$294
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/216:10 pmPNS - MDW
1 stop6h 35mSouthwest
vie. 1/25:25 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/15$304
This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/213:42 pmPNS - ORD
1 stop5h 32mDelta
vie. 1/25:30 amORD - PNS
1 stop4h 11mDelta
Deal found 12/15$304
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/237:20 amPNS - ORD
1 stop6h 52mAmerican Airlines
vie. 1/210:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Deal found 12/16$329
This American Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/294:19 pmPNS - ORD
1 stop8h 24mAmerican Airlines
dom. 1/45:21 amORD - PNS
1 stop5h 18mAmerican Airlines
Deal found 12/15$353
This American Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/211:12 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
vie. 1/25:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Deal found 12/15$354
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/307:20 amPNS - MDW
1 stop10h 35mSouthwest
lun. 1/55:10 amMDW - PNS
1 stop6h 15mSouthwest
Deal found 12/15$358
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/307:20 amPNS - MDW
1 stop10h 35mSouthwest
dom. 1/45:25 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/15$393
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/1912:05 pmPNS - MDW
1 stop4h 55mSouthwest
dom. 12/215:25 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/15$399

Find flight deals from Pensacola to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated diciembre 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$178
(Kiwi.com)

One-way from

$81
(Frontier)

Popular in

March

Cheapest in

February

Average price

$353

Good round-trip deal

$288 or less

Good one-way deal

$219 or less
Provider with most accurate pricing for Pensacola-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pensacola-Chicago (CHI) flights.
Search Deals
From Pensacola to Chicago (CHI)
Search Deals
One-way flight from Pensacola to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Pensacola to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Pensacola to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pensacola to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 16, 2025.
Use the filters below to find and compare flights from Pensacola to Chicago that are best for you.

Fly from

Pensacola

Fly to

Chicago

Route

Depart

Return

Price

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

vie. 1/16

5:33 pm-12:08 pm

2 stops18h 35m

Chicago O'Hare Intl

dom. 1/18

10:48 am-4:37 pm

1 stop5h 49m

$206

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

jue. 3/5

7:00 am-9:39 am

Nonstop2h 39m

Chicago O'Hare Intl

mar. 3/10

10:50 am-1:16 pm

Nonstop2h 26m

$209

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

lun. 2/16

5:20 pm-10:39 am

2 stops17h 19m

Chicago O'Hare Intl

jue. 2/19

3:40 pm-3:54 pm

1 stop24h 14m

$217

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

jue. 3/5

5:25 pm-7:40 pm

Nonstop2h 15m

Chicago Midway

mar. 3/10

10:30 am-4:15 pm

1 stop5h 45m

$219

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

vie. 1/16

12:35 pm-4:29 pm

1 stop3h 54m

Chicago Midway

lun. 1/19

6:00 am-12:35 pm

1 stop6h 35m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

vie. 1/16

12:35 pm-4:29 pm

1 stop3h 54m

Chicago Midway

dom. 1/18

6:45 am-1:53 pm

1 stop7h 08m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

dom. 1/18

4:00 pm-10:05 pm

1 stop6h 05m

Chicago Midway

mar. 1/20

6:00 am-9:50 am

1 stop3h 50m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

jue. 3/5

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

mar. 3/10

12:47 pm-4:35 pm

1 stop3h 48m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

vie. 1/30

7:50 am-1:20 pm

1 stop5h 30m

Chicago Midway

dom. 2/1

1:15 pm-6:50 pm

1 stop5h 35m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

dom. 1/25

6:07 pm-10:22 pm

1 stop4h 15m

Chicago Midway

mar. 1/27

6:00 am-12:35 pm

1 stop6h 35m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 52 results
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Compare providers for flights from Pensacola to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pensacola to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pensacola-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Pensacola-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Pensacola-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pensacola-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pensacola-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pensacola to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pensacola with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Pensacola to Chicago

How far ahead should I book a flight from Pensacola to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Pensacola to Chicago. Price data was last updated on December 12, 2025.

The price you pay for your flight from Pensacola to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 37 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Pensacola to Chicago?

Currently, June is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $118). Flying from Pensacola to Chicago in April is currently the most expensive (average of $232). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PNS to CHI?

Find hourly flight availability from Pensacola to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 16, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 36% on flights from Pensacola to Chicago by exploring options for tickets in the evening.

How much does it cost to fly round-trip from Pensacola to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated diciembre 16, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Pensacola to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,049 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,186 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Pensacola to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Pensacola to Chicago?

    Located just 4.0 mi from the city center, Pensacola is the airport most travelers will use when flying to Chicago from Pensacola. Booking flights from Pensacola (PNS) to Chicago should be relatively easy as there is 1 daily outbound flight to Chicago from 5 different airlines.

  • How long is the flight from Pensacola to Chicago?

    Departing from Pensacola to Chicago will take you 2h 15m. The distance from Pensacola to Chicago is about 782 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Pensacola to Chicago round-trip?

    Our cheapest airline available from Pensacola to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $155 on this airline. Additional options worth looking into are Southwest and Delta, starting at $173 and $194 round-trip. Spirit Airlines is 50% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Pensacola to Chicago one-way?

    The cheapest airlines for a one-way flight from Pensacola to Chicago are Spirit Airlines ($87), Delta ($98), and United Airlines ($104).

  • What are the most popular routes from Pensacola to Chicago?

    Most travelers choose Pensacola - Chicago O'Hare Intl, Pensacola - Chicago Midway or Pensacola - Chicago Greater Rockford when deciding on the best route from Pensacola to Chicago.

  • What are the most reliable airlines from Pensacola to Chicago?

    The top 3 most reliable airlines when flying from Pensacola to Chicago are Lufthansa (96%), Emirates (81%) and American Airlines (79%).

  • What are the cheapest flights from Pensacola to Chicago?

    On average you can expect to pay $402 for a flight from Pensacola to Chicago. The cheapest flight overall is $122 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $182.

  • Can I find deals for flights from Pensacola to Chicago that include hotel bookings?

    Yes. In addition to deals on Pensacola to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pensacola to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pensacola to Chicago.

  • Can I find deals for business class flights from Pensacola to Chicago?

    Yes. Cheapflights offers flight deals from Pensacola to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pensacola to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $118). Flying from Pensacola to Chicago in April is currently the most expensive (average of $232). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Pensacola to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Pensacola to Chicago

Discover the top 5 airlines that operate flights from Pensacola to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$317FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$295FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$307FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$330FlexibilityNo cancel feeOn-time71%

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