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$43+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from Pensacola to Chicago are usually found in January or April, booked 83 days in advance, depart on a Thursday or Wednesday 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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$96
(Cheapflightsfares)

One-way from

$45
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$353

Good round-trip deal

$229 or less

Good one-way deal

$194 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. 4% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/2011:32 amPNS - ORD
Nonstop2h 36mSpirit Airlines
jue. 3/278:14 amORD - PNS
Nonstop2h 23mSpirit Airlines
Deal found 2/18$96
This Mytrip deal was found by Cheapflights users on 2/19. 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. 4/35:23 pmPNS - ORD
1 stop6h 36mMultiple Airlines
sáb. 4/57:45 pmORD - PNS
2 stops20h 00mMultiple Airlines
Deal found 2/19$207
This Southwest deal was found by Cheapflights users on 2/19. 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. 4/32:50 pmPNS - MDW
1 stop4h 50mSouthwest
sáb. 4/56:10 amMDW - PNS
1 stop4h 50mSouthwest
Deal found 2/19$223
This United Airlines deal was found by Cheapflights users on 2/19. 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.
sáb. 3/82:10 pmPNS - ORD
Nonstop2h 38mUnited Airlines
mar. 3/1110:47 amORD - PNS
Nonstop2h 25mUnited Airlines
Deal found 2/19$229
This Delta deal was found by Cheapflights users on 2/18. 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.
vie. 10/311:59 pmPNS - MDW
1 stop4h 04mDelta
lun. 11/33:40 pmMDW - PNS
1 stop5h 01mDelta
Deal found 2/18$239
This Frontier deal was found by Cheapflights users on 2/18. 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.
sáb. 2/225:36 pmPNS - MDW
1 stop6h 41mFrontier
lun. 2/246:40 amMDW - PNS
1 stop11h 47mFrontier
Deal found 2/18$248
This Gotogate deal was found by Cheapflights users on 2/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/287:27 pmPNS - ORD
1 stop21h 58mFrontier
lun. 3/36:50 amORD - PNS
1 stop11h 37mFrontier
Deal found 2/19$259
This Southwest deal was found by Cheapflights users on 2/18. 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. 4/101:15 pmPNS - ORD
2 stops8h 15mSouthwest
mar. 4/154:00 pmORD - PNS
1 stop6h 10mSouthwest
Deal found 2/18$263
This American Airlines deal was found by Cheapflights users on 2/20. 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. 8/112:26 pmPNS - ORD
1 stop8h 10mAmerican Airlines
dom. 8/245:10 amORD - PNS
1 stop7h 03mAmerican Airlines
Deal found 2/20$289
This Delta deal was found by Cheapflights users on 2/18. 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.
vie. 10/317:15 pmPNS - ORD
1 stop4h 40mDelta
dom. 11/25:00 amORD - PNS
1 stop6h 49mDelta
Deal found 2/18$304

Find flights from Pensacola to Chicago within your budget

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 febrero 20, 2025.

Fly from

Pensacola

Fly to

Chicago

Route

Depart

Return

Price

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

jue. 3/20

11:32 am-2:08 pm

Nonstop2h 36m

Chicago O'Hare Intl

jue. 3/27

8:14 am-10:37 am

Nonstop2h 23m

$96

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

jue. 4/3

5:23 pm-11:59 pm

1 stop6h 36m

Chicago O'Hare Intl

sáb. 4/5

7:45 pm-3:45 pm

2 stops20h 00m

$207

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

jue. 4/3

2:50 pm-7:40 pm

1 stop4h 50m

Chicago Midway

sáb. 4/5

6:10 am-11:00 am

1 stop4h 50m

$223

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

sáb. 3/8

2:10 pm-4:48 pm

Nonstop2h 38m

Chicago O'Hare Intl

mar. 3/11

10:47 am-1:12 pm

Nonstop2h 25m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

sáb. 3/8

6:03 pm-10:20 pm

1 stop4h 17m

Chicago Midway

mar. 3/11

4:59 pm-11:11 pm

1 stop6h 12m

$249

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

jue. 4/10

1:15 pm-9:30 pm

2 stops8h 15m

Chicago O'Hare Intl

mar. 4/15

4:00 pm-10:10 pm

1 stop6h 10m

$263

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

lun. 8/11

2:26 pm-10:36 pm

1 stop8h 10m

Chicago O'Hare Intl

dom. 8/24

5:10 am-12:13 pm

1 stop7h 03m

$289

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

jue. 5/8

7:15 pm-12:06 am

1 stop4h 51m

Chicago O'Hare Intl

dom. 5/11

5:50 am-10:45 am

1 stop4h 55m

$344

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

vie. 6/6

4:35 pm-12:27 am

1 stop7h 52m

Chicago Midway

lun. 6/9

6:15 am-3:34 pm

1 stop9h 19m

$621

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

mié. 3/19

9:58 am-6:56 pm

1 stop8h 58m

$43

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 20 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub the most. FlightHub 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.

Travel insights for flights from Pensacola to Chicago

Get recent, data-driven insights about flights from Pensacola to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 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 febrero 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 49% on flights from Pensacola to Chicago by exploring options for tickets in the afternoon.

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 Wednesday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 febrero 20, 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
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,013 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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 $96 on this airline. Additional options worth looking into are Southwest and Delta, starting at $223 and $263 round-trip. Spirit Airlines is 71% 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 ($45), Frontier ($65), and Southwest ($105).

  • 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 Emirates (80%), Air New Zealand (80%) and Lufthansa (78%).

  • What are the cheapest flights from Pensacola to Chicago?

    On average you can expect to pay $1,021 for a flight from Pensacola to Chicago. The cheapest flight overall is $133 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $122.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$188FlexibilityNo cancel feeOn-time65%
DeltaCheapest$197Average$320FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$207Average$316FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$229Average$368FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$270Average$407FlexibilityNo cancel feeOn-time69%
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