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$55+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chicago are usually found in November or February, booked 37 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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 octubre 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$55
(Frontier)

Popular in

March

Cheapest in

November

Average price

$349

Good round-trip deal

$258 or less

Good one-way deal

$125 or less
Provider with most accurate pricing for Pensacola-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Chicago (CHI) flights.
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From Pensacola to Chicago (CHI)
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One-way flight from Pensacola to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Pensacola to Chicago (CHI).
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Price to beat on a one-way flight from Pensacola to Chicago (CHI).
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Find 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 octubre 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/42:15 pmPNS - ORD
Nonstop2h 32mUnited Airlines
jue. 12/1810:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Deal found 10/26$209
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
vie. 11/1411:17 amPNS - ORD
1 stop27h 51mMultiple Airlines
jue. 11/206:48 amORD - PNS
1 stop6h 01mMultiple Airlines
Deal found 10/27$210
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
lun. 11/1711:17 amPNS - ORD
2 stops12h 54mMultiple Airlines
vie. 12/53:14 pmORD - PNS
1 stop24h 50mMultiple Airlines
Deal found 10/27$214
This Mytrip deal was found by Cheapflights users on 10/29. 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.
mié. 11/128:16 pmPNS - ORD
2 stops18h 15mSpirit Airlines
jue. 11/2010:12 amORD - PNS
1 stop8h 59mSpirit Airlines
Deal found 10/29$218
This American Airlines deal was found by Cheapflights users on 10/27. 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.
jue. 12/111:00 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
dom. 12/149:45 amORD - PNS
Nonstop2h 34mAmerican Airlines
Deal found 10/27$219
This Mytrip deal was found by Cheapflights users on 10/27. 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. 11/118:16 pmPNS - ORD
2 stops18h 15mSpirit Airlines
sáb. 11/1510:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Deal found 10/27$220
This Mytrip deal was found by Cheapflights users on 10/26. 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.
jue. 12/47:09 pmPNS - ORD
1 stop16h 04mSpirit Airlines
sáb. 12/137:10 amORD - PNS
1 stop11h 04mSpirit Airlines
Deal found 10/26$223
This Southwest deal was found by Cheapflights users on 10/28. 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.
jue. 12/44:15 pmPNS - MDW
1 stop4h 00mSouthwest
lun. 12/810:50 amMDW - PNS
1 stop4h 45mSouthwest
Deal found 10/28$224
This Kiwi.com deal was found by Cheapflights users on 10/28. 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. 11/124:44 pmPNS - ORD
2 stops17h 57mMultiple Airlines
dom. 11/165:25 amORD - PNS
1 stop28h 57mMultiple Airlines
Deal found 10/28$224
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
jue. 11/271:44 pmPNS - ORD
1 stop9h 22mMultiple Airlines
jue. 12/46:15 amORD - PNS
1 stop11h 59mMultiple Airlines
Deal found 10/27$227
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/314:30 pmPNS - ORD
1 stop7h 46mFrontier
dom. 11/25:00 amORD - PNS
1 stop9h 35mFrontier
Deal found 10/28$228
This Southwest deal was found by Cheapflights users on 10/28. 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.
jue. 12/44:15 pmPNS - MDW
1 stop6h 20mSouthwest
dom. 12/75:10 amMDW - PNS
1 stop6h 15mSouthwest
Deal found 10/28$229

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 octubre 29, 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

jue. 12/4

2:15 pm-4:47 pm

Nonstop2h 32m

Chicago O'Hare Intl

jue. 12/18

10:55 am-1:31 pm

Nonstop2h 36m

$209

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

mié. 11/12

8:16 pm-11:12 am

1 stop14h 56m

Chicago O'Hare Intl

jue. 11/20

10:12 am-7:11 pm

1 stop8h 59m

$218

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

mié. 12/10

4:15 pm-8:15 pm

1 stop4h 00m

Chicago Midway

mié. 12/17

10:50 am-3:35 pm

1 stop4h 45m

$224

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

jue. 12/18

6:00 am-9:54 am

1 stop3h 54m

Chicago Midway

dom. 12/21

6:00 am-12:37 pm

1 stop6h 37m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

lun. 11/24

8:00 am-11:52 am

1 stop3h 52m

Chicago Midway

lun. 12/1

6:00 am-12:41 pm

1 stop6h 41m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

jue. 12/18

5:30 pm-9:15 pm

1 stop3h 45m

Chicago Midway

lun. 12/22

5:25 am-9:10 am

1 stop3h 45m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

mié. 11/12

2:17 pm-4:48 pm

Nonstop2h 31m

Chicago O'Hare Intl

jue. 11/20

10:49 am-1:15 pm

Nonstop2h 26m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

jue. 11/27

10:05 am-3:05 pm

1 stop5h 00m

Chicago Midway

jue. 12/4

12:25 pm-6:35 pm

1 stop6h 10m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

dom. 12/7

6:00 am-10:14 am

1 stop4h 14m

Chicago O'Hare Intl

lun. 12/8

5:30 am-10:41 am

1 stop5h 11m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

jue. 12/4

4:15 pm-10:35 pm

1 stop6h 20m

Chicago Midway

dom. 12/7

5:10 am-11:25 am

1 stop6h 15m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 44 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 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 October 24, 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 December is currently the most expensive (average of $235). 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 octubre 29, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 38% 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 octubre 29, 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
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
8,114 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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 are 2 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Pensacola to Chicago?

    Departing from Pensacola to Chicago will take you 2h 32m. The distance from Pensacola to Chicago is about 795 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 United Airlines ($105), Frontier ($114), and Southwest ($115).

  • 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 United Airlines (88%), Lufthansa (86%) and Emirates (85%).

  • What are the cheapest flights from Pensacola to Chicago?

    On average you can expect to pay $265 for a flight from Pensacola to Chicago. The cheapest flight overall is $104 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $175.

  • 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 December is currently the most expensive (average of $235). 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
Merrillville
Lansing
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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$317FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$297FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$238Average$310FlexibilityNo cancel feeOn-time71%

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