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Pensacola

$70+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pensacola are usually found in January or April, 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 September 15, 2025.

Round-trip from

$203
(American Airlines)

One-way from

$70
(Southwest)

Popular in

December

Cheapest in

January

Average price

$304

Good round-trip deal

$264 or less

Good one-way deal

$135 or less
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. 0% potential increase in price ($1 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 September 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 11/1910:30 amORD - PNS
Nonstop2h 30mAmerican Airlines
Mon 11/241:17 pmPNS - ORD
Nonstop2h 38mAmerican Airlines
Deal found 9/13$203
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:50 amORD - PNS
1 stop9h 40mFrontier
Mon 11/35:07 pmPNS - ORD
1 stop7h 08mFrontier
Deal found 9/14$204
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:41 amORD - PNS
1 stop6h 55mSpirit Airlines
Sun 11/94:41 pmPNS - ORD
1 stop7h 01mSpirit Airlines
Deal found 9/14$206
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Mon 11/310:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Sat 11/152:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 9/13$209
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amORD - PNS
1 stop9h 35mFrontier
Fri 11/74:30 pmPNS - ORD
1 stop7h 45mFrontier
Deal found 9/14$210
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/125:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Sun 10/194:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/14$211
This Frontier deal was found by Cheapflights users on 9/13. 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.
Sat 11/17:15 amORD - PNS
1 stop8h 20mFrontier
Sun 11/164:30 pmPNS - ORD
1 stop7h 45mFrontier
Deal found 9/13$213
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Sat 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/14$214
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/211:26 pmORD - PNS
1 stop5h 51mDelta
Wed 10/297:00 amPNS - ORD
1 stop5h 16mDelta
Deal found 9/15$217
This Southwest deal was found by Cheapflights users on 9/14. 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 10/88:40 amMDW - PNS
1 stop6h 45mSouthwest
Tue 10/1410:10 amPNS - MDW
1 stop5h 45mSouthwest
Deal found 9/14$217
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 11/1910:50 amMDW - PNS
1 stop4h 45mSouthwest
Wed 11/269:50 amPNS - MDW
1 stop7h 00mSouthwest
Deal found 9/15$218
This Booking.com deal was found by Cheapflights users on 9/13. 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.
Wed 10/156:00 amORD - PNS
1 stop11h 01mSpirit Airlines
Sun 10/194:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/13$219

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 September 15, 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

Wed 10/8

8:40 am-3:25 pm

1 stop6h 45m

Pensacola

Tue 10/14

10:10 am-3:55 pm

1 stop5h 45m

$217

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 10/21

1:26 pm-7:17 pm

1 stop5h 51m

Pensacola

Wed 10/29

7:00 am-12:16 pm

1 stop5h 16m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/19

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Wed 11/26

9:50 am-4:50 pm

1 stop7h 00m

$218

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 11/4

10:40 am-3:05 pm

1 stop4h 25m

Pensacola

Fri 11/14

6:00 am-9:51 am

1 stop3h 51m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 10/26

5:35 am-9:10 am

1 stop3h 35m

Pensacola

Wed 10/29

2:30 pm-6:10 pm

1 stop3h 40m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 12/2

9:50 am-4:35 pm

1 stop6h 45m

Pensacola

Thu 12/4

5:45 pm-9:53 pm

1 stop4h 08m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 10/8

8:40 am-3:25 pm

1 stop6h 45m

Pensacola

Mon 10/13

7:35 pm-11:15 pm

1 stop3h 40m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 2/11

5:50 am-10:49 am

1 stop4h 59m

Pensacola

Mon 2/16

7:15 pm-11:54 pm

1 stop4h 39m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 2/14

5:50 am-10:49 am

1 stop4h 59m

Pensacola

Wed 2/18

1:59 pm-9:14 pm

1 stop7h 15m

$224

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 10/13

5:30 am-11:30 am

1 stop6h 00m

Pensacola

Mon 10/20

12:05 pm-8:55 pm

1 stop8h 50m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 43 results
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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 September 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 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, September is the cheapest month in which you can book a flight from Chicago to Pensacola (average of $303). Flying from Chicago to Pensacola in March is currently the most expensive (average of $415). 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 September 15, 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 morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 24% 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 September 14, 2025.

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

Weekly flight availability from Chicago to Pensacola

Explore weekly flight availability from Chicago to Pensacola. 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 September 15, 2025.

The most flights from CHI to PNS are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 50% 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 September 15, 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
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

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 2 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Pensacola?

    Southwest and Delta can get you from Chicago to Pensacola in just under 5h 51m. Your travel time can differ by up to 54m. 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 $196, and Southwest, from $214. Spirit Airlines is priced at 65% 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?

    $70 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Spirit Airlines, with prices starting from $89 and $91, 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 (90%), Air New Zealand (90%), American Airlines( 80%).

  • What are the cheapest flights from Chicago to Pensacola?

    Looking at all options, your cheapest flight can be booked for $107. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $177 on average, our data indicates $368 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, September is the cheapest month in which you can book a flight from Chicago to Pensacola (average of $303). Flying from Chicago to Pensacola in March is currently the most expensive (average of $415). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$303FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$214Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$225Average$319FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$391FlexibilityNo cancel feeOn-time69%

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