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Pensacola

$89+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Find cheap flights from Chicago to Pensacola with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Pensacola are usually found in September or November, booked 62 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap 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 December 16, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Mon 12/294:19 pmPNS - ORD
1 stop6h 40mAmerican Airlines
Deal found 12/15$304
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Sun 12/215:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Wed 12/2412:58 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 12/14$329
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/225:21 amORD - PNS
1 stop5h 18mAmerican Airlines
Sat 12/275:15 amPNS - ORD
1 stop5h 30mAmerican Airlines
Deal found 12/14$339
This Southwest deal was found by Cheapflights users on 12/16. 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.
Tue 12/235:00 amMDW - PNS
1 stop6h 15mSouthwest
Sat 12/272:00 pmPNS - MDW
1 stop9h 55mSouthwest
Deal found 12/16$344
This Southwest deal was found by Cheapflights users on 12/14. 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.
Wed 12/315:35 amMDW - PNS
1 stop3h 45mSouthwest
Sun 1/46:10 pmPNS - MDW
1 stop4h 40mSouthwest
Deal found 12/14$348
This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:30 amORD - PNS
1 stop5h 33mSpirit Airlines
Tue 12/301:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Deal found 12/15$351
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/264:05 pmORD - PNS
1 stop5h 05mAmerican Airlines
Mon 1/56:10 amPNS - ORD
1 stop7h 04mAmerican Airlines
Deal found 12/15$353
This Mytrip deal was found by Cheapflights users on 12/14. 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.
Mon 12/297:30 amORD - PNS
1 stop10h 44mSpirit Airlines
Tue 1/61:58 pmPNS - ORD
3 stops30h 06mSpirit Airlines
Deal found 12/14$355
This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:30 amORD - PNS
1 stop10h 44mSpirit Airlines
Wed 12/241:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Deal found 12/15$368
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Sun 12/2110:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Thu 12/2512:58 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 12/14$379
This Booking.com deal was found by Cheapflights users on 12/15. 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.
Tue 12/167:10 amORD - PNS
1 stop6h 03mSpirit Airlines
Tue 12/231:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Deal found 12/15$386
This Southwest deal was found by Cheapflights users on 12/15. 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.
Tue 12/235:25 amMDW - PNS
1 stop3h 45mSouthwest
Tue 12/2312:05 pmPNS - MDW
1 stop4h 55mSouthwest
Deal found 12/15$388

Find 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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$222
(Expedia)

One-way from

$89
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$343

Good round-trip deal

$273 or less

Good one-way deal

$254 or less
Provider with most accurate pricing for Chicago (CHI)-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Pensacola flights.
Search Deals
From Chicago (CHI) to Pensacola
Search Deals
One-way flight from Chicago (CHI) to Pensacola
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Pensacola.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Pensacola.
Search Deals

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 December 16, 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

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/16

5:31 pm-11:13 pm

1 stop5h 42m

Pensacola

Wed 2/4

1:40 pm-5:29 pm

1 stop3h 49m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 1/8

6:00 am-9:50 am

1 stop3h 50m

Pensacola

Sun 1/11

4:25 pm-10:30 pm

1 stop6h 05m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 3/6

10:50 am-1:16 pm

Nonstop2h 26m

Pensacola

Mon 3/9

7:00 am-9:38 am

Nonstop2h 38m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Tue 2/24

1:37 pm-5:45 pm

1 stop4h 08m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 3/7

7:55 am-2:25 pm

1 stop6h 30m

Pensacola

Sat 3/7

5:20 pm-12:50 am

1 stop7h 30m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 1/14

6:45 am-11:39 am

1 stop4h 54m

Pensacola

Thu 2/5

1:40 pm-5:29 pm

1 stop3h 49m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 1/17

6:45 am-1:49 pm

1 stop7h 04m

Pensacola

Sun 1/18

6:00 am-10:27 am

1 stop4h 27m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 3/16

5:38 pm-10:01 pm

1 stop4h 23m

Pensacola

Tue 3/24

7:15 am-12:02 pm

1 stop4h 47m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 1/15

6:45 am-1:53 pm

1 stop7h 08m

Pensacola

Mon 1/19

4:04 pm-10:22 pm

1 stop6h 18m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 1/14

6:45 am-11:39 am

1 stop4h 54m

Pensacola

Sat 1/31

11:25 am-3:38 pm

1 stop4h 13m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 39 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 December.
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 December 12, 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 62 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 December is currently the most expensive (average of $208). 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 December 16, 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 42% 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 December 13, 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 December 16, 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
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

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
8,008 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

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
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

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
11,049 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

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
8,186 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

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 1 inbound flight from Chicago per day.

  • How long is the flight from Chicago to Pensacola?

    Delta, Southwest, and United Airlines can get you from Chicago to Pensacola in just under 2h 26m. Your travel time can differ by up to 3h 16m. 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 $116. Other airlines that can offer you cheap pricing are Delta, from $176, and United Airlines, from $210. 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?

    $62 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $88 and $98, respectively.

  • What are the most reliable airlines from Chicago to Pensacola?

    Before booking your flight to Pensacola from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (83%), Air New Zealand (76%), Envoy Air( 71%).

  • What are the cheapest flights from Chicago to Pensacola?

    Looking at all options, your cheapest flight can be booked for $153. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $170 on average, our data indicates $311 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 December is currently the most expensive (average of $208). 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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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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$283FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$214Average$368FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$214Average$373FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$218Average$318FlexibilityNo cancel feeOn-time71%

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