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Pensacola

$61+ Cheap flights from Chicago (CHI) to Pensacola (PNS)

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pensacola are usually found in September or January, booked 16 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pensacola (PNS). 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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$61
(Priceline)

Popular in

March

Cheapest in

September

Average price

$339

Good round-trip deal

$236 or less

Good one-way deal

$136 or less
Provider with most accurate pricing for Chicago (CHI)-Pensacola flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Pensacola flights.
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From Chicago (CHI) to Pensacola
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One-way flight from Chicago (CHI) to Pensacola
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 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 Chicago (CHI) to Pensacola.
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Price to beat on a one-way flight from Chicago (CHI) to Pensacola.
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Find flight deals from Chicago to Pensacola

Cheapest flights from Chicago to Pensacola
Explore the most affordable flight options available from Chicago to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2010:49 amORD - PNS
Nonstop2h 26mUnited Airlines
lun. 11/242:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 10/28$209
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/1110:00 amORD - PNS
2 stops9h 11mSpirit Airlines
vie. 11/1411:17 amPNS - ORD
1 stop11h 49mSpirit Airlines
Deal found 10/28$210
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.
mar. 11/187:34 pmORD - PNS
2 stops23h 37mSpirit Airlines
jue. 11/201:44 pmPNS - ORD
1 stop9h 22mSpirit Airlines
Deal found 10/29$211
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.
mié. 11/197:34 pmORD - PNS
2 stops17h 15mSpirit Airlines
lun. 11/245:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 10/27$214
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/206:23 pmORD - PNS
1 stop22h 36mMultiple Airlines
lun. 11/248:16 pmPNS - ORD
1 stop23h 05mMultiple Airlines
Deal found 10/29$216
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.
mié. 11/121:48 pmORD - PNS
3 stops29h 23mSpirit Airlines
lun. 11/178:16 pmPNS - ORD
1 stop13h 31mSpirit Airlines
Deal found 10/27$218
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/1510:49 amORD - PNS
Nonstop2h 26mUnited Airlines
mar. 11/182:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 10/28$219
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.
sáb. 11/158:00 amORD - PNS
1 stop26h 22mMultiple Airlines
mié. 11/198:16 pmPNS - ORD
1 stop20h 55mMultiple Airlines
Deal found 10/28$221
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/310:50 amORD - PNS
Nonstop2h 27mUnited Airlines
dom. 12/72:15 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Deal found 10/28$223
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/117:10 amORD - PNS
1 stop11h 04mSpirit Airlines
dom. 12/147:09 pmPNS - ORD
1 stop16h 04mSpirit Airlines
Deal found 10/28$224
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/910:50 amMDW - PNS
1 stop4h 45mSouthwest
mar. 12/164:15 pmPNS - MDW
1 stop4h 00mSouthwest
Deal found 10/29$224
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/127:34 pmORD - PNS
2 stops23h 37mSpirit Airlines
vie. 11/1411:17 amPNS - ORD
1 stop11h 49mSpirit Airlines
Deal found 10/28$225

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Pensacola 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 30, 2025.
Use the filters below to find and compare flights from Chicago to Pensacola that are best for you.

Fly from

Chicago

Fly to

Pensacola

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

jue. 11/27

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

jue. 12/4

2:15 pm-4:47 pm

Nonstop2h 32m

$209

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

jue. 11/20

6:00 am-10:41 am

1 stop4h 41m

Pensacola

mar. 11/25

5:00 pm-11:40 pm

1 stop6h 40m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

sáb. 12/6

12:00 pm-5:00 pm

1 stop5h 00m

Pensacola

lun. 12/8

4:15 pm-8:15 pm

1 stop4h 00m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

jue. 12/11

6:00 am-12:41 pm

1 stop6h 41m

Pensacola

dom. 12/14

5:45 pm-11:47 pm

1 stop6h 02m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

vie. 1/23

7:05 am-12:45 pm

1 stop5h 40m

Pensacola

vie. 2/6

6:07 pm-11:57 pm

1 stop5h 50m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 1/27

7:05 am-12:45 pm

1 stop5h 40m

Pensacola

sáb. 2/7

6:00 am-10:15 am

1 stop4h 15m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mié. 1/28

5:33 am-10:28 am

1 stop4h 55m

Pensacola

jue. 2/5

1:40 pm-8:59 pm

1 stop7h 19m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

vie. 1/23

5:54 pm-11:12 pm

1 stop5h 18m

Pensacola

mar. 2/10

7:00 am-1:39 pm

1 stop6h 39m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

dom. 1/25

5:54 pm-11:12 pm

1 stop5h 18m

Pensacola

sáb. 2/7

1:59 pm-7:21 pm

1 stop5h 22m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 1/27

5:33 am-10:28 am

1 stop4h 55m

Pensacola

jue. 2/5

1:40 pm-6:49 pm

1 stop5h 09m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 42 results
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Compare providers for flights from Chicago to Pensacola

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 Chicago to Pensacola in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice 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 Chicago-Pensacola flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Pensacola flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Pensacola 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 Chicago-Pensacola 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 Chicago to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from Chicago 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 Chicago to Pensacola

How far ahead should I book a flight from Chicago to Pensacola?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Pensacola. Price data was last updated on October 24, 2025.

The price you pay for your flight from Chicago to Pensacola may vary depending on when you book. For the best chance of a lower fare, look to book 16 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 Chicago to Pensacola?

Currently, July is the cheapest month in which you can book a flight from Chicago to Pensacola (average of $81). Flying from Chicago to Pensacola in August is currently the most expensive (average of $200). 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 CHI to PNS?

Find hourly flight availability from Chicago to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 30, 2025.

One of the essential ways to save on airfare from Chicago to Pensacola is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 51% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Pensacola. Price data was last updated on October 26, 2025.

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

What’s the top layover airport for flights from Chicago to Pensacola?

Share of 1-stop round-trip flights from Chicago to Pensacola chosen by Cheapflights users in the past 12 months, using the same layover each way.

St. Louis (STL) – chosen by Cheapflights users on 60% of 1-stop itineraries from Chicago to Pensacola on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Pensacola?

Average round-trip fare for 1-stop flights from Chicago to Pensacola, chosen by Cheapflights users in the past 12 months, with the same layover each way.

St. Louis (STL) is the most affordable 1-stop option, with an average round-trip price of $185.

What’s the fastest layover option from Chicago to Pensacola?

Shortest average travel time for 1-stop one-way flights from Chicago to Pensacola, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via St. Louis (STL) have the shortest average one-way travel time for 1-stop routes: 3h 50m.

Which airport typically offers the quickest layover for flights from Chicago to Pensacola?

Average layover duration for 1-stop one-way flights from Chicago to Pensacola, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via St. Louis (STL) offer the fastest connection on this route, with an average layover time of 0h 55m.

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. 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 Pensacola. Reviews last updated octubre 30, 2025.
Read through reviews of airlines operating flights from Chicago to Pensacola, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Pensacola. 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 into for flights to Pensacola from Chicago?

    Pensacola (PNS), located 4.0 mi from the city center, is the airport you fly into when you book flights from Chicago to Pensacola. 5 airlines have flights to Pensacola from Chicago on a regular basis. Booking flights from Chicago to Pensacola should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Pensacola?

    United Airlines, Delta, and Southwest can get you from Chicago to Pensacola in just under 2h 26m. Your travel time can differ by up to 2h 34m. Chicago and Pensacola are separated by a distance of 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 Chicago to Pensacola round-trip?

    Cheapflights users have booked flights from Chicago to Pensacola round-trip from $118. Other airlines that can offer you cheap pricing are Delta, from $177, and Southwest, from $216. Spirit Airlines is priced at 64% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Pensacola one-way?

    $105 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $110 and $115, respectively.

  • What are the cheapest flights from Chicago to Pensacola?

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $162 on average, our data indicates $269 when flying from Chicago to Pensacola.

  • Can I find deals for flights from Chicago to Pensacola that include hotel bookings?

    Yes. In addition to deals on Chicago to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Pensacola.

  • Can I find deals for business class flights from Chicago to Pensacola?

    Yes. Cheapflights offers flight deals from Chicago to Pensacola 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 Chicago to Pensacola?

    Currently, July is the cheapest month in which you can book a flight from Chicago to Pensacola (average of $81). Flying from Chicago to Pensacola in August is currently the most expensive (average of $200). 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
Gulf Breeze
Navarre
Foley
Perdido Key
Navarre Beach
Warrington

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Alternative routes for Chicago to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Pensacola

Discover the top 5 airlines that operate flights from Chicago to Pensacola. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$279FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$318FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$379FlexibilityNo cancel feeOn-time69%

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