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$76+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chicago are usually found in February or January, booked 83 days in advance, depart on a Thursday or Saturday 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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$151
(Cheapflightsfares)

One-way from

$76
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$318

Good round-trip deal

$300 or less

Good one-way deal

$153 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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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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).
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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 April 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/134:35 pmPNS - ORD
1 stop6h 29mSpirit Airlines
Tue 5/205:05 amORD - PNS
1 stop10h 25mSpirit Airlines
Deal found 4/15$151
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/132:05 pmPNS - ORD
Nonstop2h 41mUnited Airlines
Tue 5/2010:40 amORD - PNS
Nonstop2h 28mUnited Airlines
Deal found 4/15$177
This Delta deal was found by Cheapflights users on 4/14. 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.
Fri 5/29:18 amPNS - MDW
1 stop6h 54mDelta
Mon 5/54:59 pmMDW - PNS
1 stop6h 11mDelta
Deal found 4/14$197
This Delta deal was found by Cheapflights users on 4/14. 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.
Thu 6/124:07 pmPNS - ORD
1 stop5h 17mDelta
Mon 6/167:10 amORD - PNS
1 stop5h 43mDelta
Deal found 4/14$197
This Southwest deal was found by Cheapflights users on 4/14. 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.
Fri 5/24:40 pmPNS - MDW
1 stop6h 20mSouthwest
Sun 5/410:45 amMDW - PNS
Nonstop2h 15mSouthwest
Deal found 4/14$222
This American Airlines deal was found by Cheapflights users on 4/14. 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.
Wed 5/216:15 amPNS - ORD
1 stop7h 37mAmerican Airlines
Sun 5/259:13 amORD - PNS
Nonstop2h 23mAmerican Airlines
Deal found 4/14$228
This Southwest deal was found by Cheapflights users on 4/15. 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.
Sat 8/93:50 pmPNS - ORD
1 stop6h 10mSouthwest
Wed 8/133:10 pmORD - PNS
1 stop3h 45mSouthwest
Deal found 4/15$232
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Sun 6/86:14 pmPNS - ORD
1 stop5h 15mMultiple Airlines
Sun 6/2211:45 amORD - PNS
2 stops19h 25mMultiple Airlines
Deal found 4/14$271
This Booking.com deal was found by Cheapflights users on 4/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/187:23 pmPNS - MDW
1 stop28h 58mFrontier
Mon 4/216:45 amMDW - PNS
1 stop11h 42mFrontier
Deal found 4/15$341
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/304:18 pmPNS - ORD
1 stop7h 34mFrontier
Fri 6/66:00 amORD - PNS
1 stop9h 29mFrontier
Deal found 4/15$353
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Sun 6/88:20 amPNS - MDW
2 stops35h 26mMultiple Airlines
Sun 6/228:09 pmMDW - PNS
3 stops35h 46mMultiple Airlines
Deal found 4/14$464

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 April 15, 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

Tue 5/13

4:35 pm-11:04 pm

1 stop6h 29m

Chicago O'Hare Intl

Tue 5/20

5:05 am-3:30 pm

1 stop10h 25m

$151

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 5/13

2:05 pm-4:46 pm

Nonstop2h 41m

Chicago O'Hare Intl

Tue 5/20

10:40 am-1:08 pm

Nonstop2h 28m

$177

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 5/2

9:18 am-4:12 pm

1 stop6h 54m

Chicago Midway

Mon 5/5

4:59 pm-11:10 pm

1 stop6h 11m

$197

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 6/12

4:07 pm-9:24 pm

1 stop5h 17m

Chicago O'Hare Intl

Mon 6/16

7:10 am-12:53 pm

1 stop5h 43m

$197

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 5/2

4:40 pm-11:00 pm

1 stop6h 20m

Chicago Midway

Sun 5/4

10:45 am-1:00 pm

Nonstop2h 15m

$222

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 5/21

6:15 am-1:52 pm

1 stop7h 37m

Chicago O'Hare Intl

Sun 5/25

9:13 am-11:36 am

Nonstop2h 23m

$228

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 6/30

6:00 am-3:00 pm

2 stops9h 00m

Chicago O'Hare Intl

Fri 7/4

7:00 am-1:45 pm

1 stop6h 45m

$243

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sun 6/8

6:14 pm-11:29 pm

1 stop5h 15m

Chicago O'Hare Intl

Sun 6/22

11:45 am-7:10 am

2 stops19h 25m

$271

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 4/18

7:23 pm-12:21 am

1 stop28h 58m

Chicago Midway

Mon 4/21

6:45 am-6:27 pm

1 stop11h 42m

$341

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 5/30

4:18 pm-11:52 pm

1 stop7h 34m

Chicago O'Hare Intl

Fri 6/6

6:00 am-3:29 pm

1 stop9h 29m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 22 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pensacola-Chicago flight deals on Cheapflights vs. FlightHub >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 April 11, 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 81 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, August is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $245). Flying from Pensacola to Chicago in March is currently the most expensive (average of $321). 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 April 15, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 45% on flights from Pensacola to Chicago by exploring options for tickets in the evening.

What is the cheapest day to fly from Pensacola to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Pensacola to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Pensacola to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Pensacola to Chicago

Explore weekly flight availability from Pensacola to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 15, 2025.

The most flights from PNS to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 15, 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. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

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
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

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
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

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
8,658 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

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
10,000 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

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
7,921 reviews
Southwest
8.0
Very good
4,279 reviews

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

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 3 daily outbound flights to Chicago from 5 different airlines.

  • 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 $151 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $177 and $197 round-trip. Spirit Airlines is 55% 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 ($76), Southwest ($89), and United Airlines ($89).

  • 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 American Airlines (100%), Qatar Airways (100%) and Envoy Air (100%).

  • What are the cheapest flights from Pensacola to Chicago?

    On average you can expect to pay $608 for a flight from Pensacola to Chicago. The cheapest flight overall is $92 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $161.

  • 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, August is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $245). Flying from Pensacola to Chicago in March is currently the most expensive (average of $321). 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 Pensacola?

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

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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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$188FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$192Average$381FlexibilityNo cancel feeOn-time63%
DeltaCheapest$207Average$320FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$323FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$253Average$406FlexibilityNo cancel feeOn-time69%

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