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$67+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chicago are usually found in February or November, booked 27 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 September 11, 2025.

Round-trip from

$154
(Southwest)

One-way from

$67
(United Airlines)

Popular in

March

Cheapest in

February

Average price

$287

Good round-trip deal

$287 or less

Good one-way deal

$179 or less
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. 6% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/152:30 pmPNS - MDW
1 stop3h 40mSouthwest
Sat 10/188:20 amMDW - PNS
2 stops5h 55mSouthwest
Deal found 9/10$154
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/74:30 pmPNS - ORD
1 stop7h 45mFrontier
Mon 11/106:00 amORD - PNS
1 stop9h 50mFrontier
Deal found 9/10$156
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/152:30 pmPNS - MDW
1 stop3h 40mSouthwest
Mon 10/205:30 amMDW - PNS
1 stop6h 00mSouthwest
Deal found 9/11$158
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 11/72:17 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Sun 11/910:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Deal found 9/11$165
This Southwest deal was found by Cheapflights users on 9/11. 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 11/75:30 pmPNS - MDW
1 stop3h 45mSouthwest
Tue 11/115:35 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 9/11$166
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Sun 10/195:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Deal found 9/8$173
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/152:30 pmPNS - MDW
1 stop3h 40mSouthwest
Sun 10/196:50 amMDW - PNS
1 stop3h 35mSouthwest
Deal found 9/11$175
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/254:20 pmPNS - MDW
1 stop5h 54mDelta
Tue 10/285:04 pmMDW - PNS
1 stop4h 43mDelta
Deal found 9/10$177
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/251:42 pmPNS - ORD
1 stop5h 07mDelta
Tue 10/284:05 pmORD - PNS
1 stop5h 42mDelta
Deal found 9/10$177
This Delta deal was found by Cheapflights users on 9/11. 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 10/246:09 pmPNS - MDW
1 stop4h 05mDelta
Wed 10/296:00 amMDW - PNS
1 stop6h 37mDelta
Deal found 9/11$181
This Delta deal was found by Cheapflights users on 9/9. 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 10/244:03 pmPNS - ORD
1 stop4h 20mDelta
Wed 10/296:00 amORD - PNS
1 stop6h 04mDelta
Deal found 9/9$181
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Thu 10/24:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Mon 10/65:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Deal found 9/9$182

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 September 11, 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 - MDW

PNSMDW

Pensacola

Wed 10/15

2:30 pm-6:10 pm

1 stop3h 40m

Chicago Midway

Sat 10/18

8:20 am-2:15 pm

2 stops5h 55m

$154

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 11/7

5:30 pm-9:15 pm

1 stop3h 45m

Chicago Midway

Tue 11/11

5:35 am-9:20 am

1 stop3h 45m

$166

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 10/15

2:30 pm-6:10 pm

1 stop3h 40m

Chicago Midway

Sun 10/19

6:50 am-10:25 am

1 stop3h 35m

$175

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 10/25

1:42 pm-6:49 pm

1 stop5h 07m

Chicago O'Hare Intl

Tue 10/28

4:05 pm-9:47 pm

1 stop5h 42m

$177

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/24

4:27 pm-10:14 pm

1 stop5h 47m

Chicago Midway

Wed 10/29

6:00 am-10:42 am

1 stop4h 42m

$181

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 11/7

2:17 pm-4:49 pm

Nonstop2h 32m

Chicago O'Hare Intl

Mon 11/10

10:49 am-1:15 pm

Nonstop2h 26m

$184

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/24

4:27 pm-10:14 pm

1 stop5h 47m

Chicago Midway

Mon 10/27

6:00 am-10:39 am

1 stop4h 39m

$185

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 10/24

4:03 pm-8:23 pm

1 stop4h 20m

Chicago O'Hare Intl

Mon 10/27

5:20 am-10:39 am

1 stop5h 19m

$185

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 10/16

7:35 pm-11:15 pm

1 stop3h 40m

Chicago Midway

Mon 10/20

4:10 pm-9:55 pm

1 stop5h 45m

$202

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 11/10

5:30 pm-11:30 pm

1 stop6h 00m

Chicago Midway

Wed 11/12

5:35 am-9:20 am

1 stop3h 45m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 44 results
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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 August 29, 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 27 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 September 11, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 37% 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 Wednesday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 11, 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
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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.

  • 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 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 (82%), United Airlines (82%) and Air New Zealand (82%).

  • What are the cheapest flights from Pensacola to Chicago?

    On average you can expect to pay $296 for a flight from Pensacola to Chicago. The cheapest flight overall is $125 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $165.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$317FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$296FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$387FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$313FlexibilityNo cancel feeOn-time71%

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