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$79+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chicago are usually found in February or September, booked 82 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 June 12, 2025.

Round-trip from

$157
(United Airlines)

One-way from

$79
(Southwest)

Popular in

March

Cheapest in

February

Average price

$327

Good round-trip deal

$227 or less

Good one-way deal

$138 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. 4% potential increase in price ($13 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 June 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 June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 8/142:08 pmPNS - ORD
Nonstop2h 39mUnited Airlines
Mon 8/1810:39 amORD - PNS
Nonstop2h 27mUnited Airlines
Deal found 6/11$157
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/78:26 pmPNS - ORD
1 stop12h 24mSpirit Airlines
Wed 7/94:36 pmORD - PNS
1 stop6h 05mSpirit Airlines
Deal found 6/10$171
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 8/125:00 pmPNS - MDW
1 stop4h 49mDelta
Wed 8/206:04 amMDW - PNS
1 stop4h 46mDelta
Deal found 6/10$177
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 8/128:05 amPNS - ORD
1 stop4h 11mDelta
Thu 8/217:05 amORD - PNS
1 stop6h 03mDelta
Deal found 6/10$177
This Southwest deal was found by Cheapflights users on 6/11. 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.
Thu 8/1412:30 pmPNS - MDW
1 stop5h 05mSouthwest
Mon 8/185:25 amMDW - PNS
2 stops6h 20mSouthwest
Deal found 6/11$182
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/236:00 amPNS - RFD
2 stops26h 31mMultiple Airlines
Sun 7/279:21 amRFD - PNS
2 stops33h 08mMultiple Airlines
Deal found 6/10$227
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:20 amPNS - ORD
1 stop6h 49mAmerican Airlines
Mon 8/187:35 amORD - PNS
1 stop5h 43mAmerican Airlines
Deal found 6/11$251
This Southwest deal was found by Cheapflights users on 6/10. 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.
Fri 8/2211:05 amPNS - ORD
2 stops10h 25mSouthwest
Mon 8/252:55 pmORD - PNS
1 stop4h 05mSouthwest
Deal found 6/10$279
This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/144:29 pmPNS - ORD
1 stop7h 30mMultiple Airlines
Mon 6/1610:46 amORD - PNS
1 stop11h 51mMultiple Airlines
Deal found 6/11$326
This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/134:29 pmPNS - MDW
1 stop28h 24mFrontier
Sun 6/152:44 pmMDW - PNS
1 stop24h 45mFrontier
Deal found 6/11$384
This Mytrip deal was found by Cheapflights users on 6/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/39:28 amPNS - MDW
3 stops28h 36mMultiple Airlines
Mon 7/710:31 amMDW - PNS
3 stops36h 06mMultiple Airlines
Deal found 6/9$541

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 June 12, 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

Thu 8/14

2:08 pm-4:47 pm

Nonstop2h 39m

Chicago O'Hare Intl

Mon 8/18

10:39 am-1:06 pm

Nonstop2h 27m

$157

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 7/7

8:26 pm-8:50 am

1 stop12h 24m

Chicago O'Hare Intl

Wed 7/9

4:36 pm-10:41 pm

1 stop6h 05m

$171

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/12

5:00 pm-9:49 pm

1 stop4h 49m

Chicago Midway

Wed 8/20

6:04 am-10:50 am

1 stop4h 46m

$177

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 8/12

8:05 am-12:16 pm

1 stop4h 11m

Chicago O'Hare Intl

Mon 8/18

7:05 am-1:08 pm

1 stop6h 03m

$177

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 8/14

12:30 pm-5:35 pm

1 stop5h 05m

Chicago Midway

Mon 8/18

5:25 am-11:45 am

2 stops6h 20m

$182

PensacolaChicago

PNS - RFD

PNSRFD

Pensacola

Wed 7/23

6:00 am-8:31 am

2 stops26h 31m

Chicago Greater Rockford

Sun 7/27

9:21 am-6:29 pm

2 stops33h 08m

$227

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 8/14

7:20 am-2:09 pm

1 stop6h 49m

Chicago O'Hare Intl

Mon 8/18

7:35 am-1:18 pm

1 stop5h 43m

$251

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 8/22

11:05 am-9:30 pm

2 stops10h 25m

Chicago O'Hare Intl

Mon 8/25

2:55 pm-7:00 pm

1 stop4h 05m

$279

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 7/4

6:00 am-8:23 pm

1 stop14h 23m

Chicago O'Hare Intl

Sun 7/6

8:15 am-6:15 pm

3 stops34h 00m

$355

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 7/3

9:28 am-2:04 pm

3 stops28h 36m

Chicago Midway

Mon 7/7

10:31 am-10:37 pm

3 stops36h 06m

$541

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 21 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 June 9, 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 June 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 44% 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. Sunday at noon 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 June 12, 2025.

The most flights from PNS to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 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 June 12, 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
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8,052 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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 5 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 United Airlines. Our recent data shows that you can find tickets from as low as $157 on this airline. Additional options worth looking into are Spirit Airlines and Delta, starting at $171 and $177 round-trip. United 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 Southwest ($79), United Airlines ($79), and Delta ($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 Spirit Airlines (100%), American Airlines (88%) and Qatar Airways (88%).

  • What are the cheapest flights from Pensacola to Chicago?

    On average you can expect to pay $964 for a flight from Pensacola to Chicago. The cheapest flight overall is $138 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $176.

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Pensacola to Chicago

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$188FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$192Average$377FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$313FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$238Average$403FlexibilityNo cancel feeOn-time69%

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