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Pensacola

$73+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pensacola are usually found in January or April, booked 62 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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$185
(Mytrip)

One-way from

$73
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$409

Good round-trip deal

$282 or less

Good one-way deal

$99 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. 1% potential increase in price ($6 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 March 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 March 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/178:45 amORD - PNS
1 stop6h 19mSpirit Airlines
Fri 4/255:57 pmPNS - ORD
1 stop7h 01mSpirit Airlines
Deal found 3/27$186
This CheapOair deal was found by Cheapflights users on 3/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/46:40 amORD - PNS
1 stop11h 43mMultiple Airlines
Sun 4/611:32 amPNS - ORD
Nonstop2h 36mMultiple Airlines
Deal found 3/26$204
This United Airlines deal was found by Cheapflights users on 3/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/110:40 amORD - PNS
Nonstop2h 27mUnited Airlines
Thu 6/55:16 pmPNS - ORD
1 stop6h 57mUnited Airlines
Deal found 3/27$213
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/34:05 pmMDW - PNS
1 stop4h 05mSouthwest
Sat 5/244:15 pmPNS - MDW
Nonstop2h 10mSouthwest
Deal found 3/27$219
This Delta deal was found by Cheapflights users on 3/26. 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 5/63:30 pmORD - PNS
1 stop5h 55mDelta
Sat 5/1011:30 amPNS - ORD
1 stop7h 50mDelta
Deal found 3/26$223
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1810:39 amMDW - PNS
1 stop6h 19mDelta
Tue 6/247:00 amPNS - MDW
1 stop4h 56mDelta
Deal found 3/27$229
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/76:45 amMDW - PNS
1 stop11h 42mFrontier
Fri 4/117:23 pmPNS - MDW
1 stop28h 58mFrontier
Deal found 3/27$230
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/221:50 pmORD - PNS
2 stops8h 20mSouthwest
Sat 4/263:15 pmPNS - ORD
1 stop6h 45mSouthwest
Deal found 3/27$238
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/108:15 amORD - PNS
Nonstop2h 24mAmerican Airlines
Thu 5/155:30 amPNS - ORD
1 stop6h 48mAmerican Airlines
Deal found 3/27$267
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Fri 3/286:30 amORD - PNS
1 stop11h 57mFrontier
Fri 4/47:23 pmPNS - ORD
1 stop17h 54mFrontier
Deal found 3/27$306
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Thu 5/2911:03 amMDW - PNS
3 stops28h 27mMultiple Airlines
Mon 6/26:00 amPNS - MDW
2 stops13h 14mMultiple Airlines
Deal found 3/27$401

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 March 28, 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

Thu 4/17

8:45 am-3:04 pm

1 stop6h 19m

Pensacola

Fri 4/25

5:57 pm-12:58 am

1 stop7h 01m

$186

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 4/4

6:40 am-6:23 pm

1 stop11h 43m

Pensacola

Sun 4/6

11:32 am-2:08 pm

Nonstop2h 36m

$204

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 6/1

10:40 am-1:07 pm

Nonstop2h 27m

Pensacola

Thu 6/5

5:16 pm-12:13 am

1 stop6h 57m

$213

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 5/3

4:05 pm-8:10 pm

1 stop4h 05m

Pensacola

Sat 5/24

4:15 pm-6:25 pm

Nonstop2h 10m

$219

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 5/6

3:30 pm-9:25 pm

1 stop5h 55m

Pensacola

Sat 5/10

11:30 am-7:20 pm

1 stop7h 50m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 6/18

10:39 am-4:58 pm

1 stop6h 19m

Pensacola

Tue 6/24

7:00 am-11:56 am

1 stop4h 56m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 4/7

6:45 am-6:27 pm

1 stop11h 42m

Pensacola

Fri 4/11

7:23 pm-12:21 am

1 stop28h 58m

$230

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 4/22

1:50 pm-10:10 pm

2 stops8h 20m

Pensacola

Sat 4/26

3:15 pm-10:00 pm

1 stop6h 45m

$238

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 5/10

8:15 am-10:39 am

Nonstop2h 24m

Pensacola

Thu 5/15

5:30 am-12:18 pm

1 stop6h 48m

$267

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 5/29

11:03 am-3:30 pm

3 stops28h 27m

Pensacola

Mon 6/2

6:00 am-7:14 pm

2 stops13h 14m

$401

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 21 results
1
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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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Pensacola flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 March 21, 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, September is the cheapest month in which you can book a flight from Chicago to Pensacola (average of $306). Flying from Chicago to Pensacola in March is currently the most expensive (average of $418). 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 March 28, 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 32% 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 March 23, 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 March 28, 2025.

The most flights from CHI to PNS are scheduled on a Thursday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Pensacola by month

Plan your trip to Pensacola by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Pensacola ranges from 4.2 - 7.4 inches per month. July is typically the wettest month, when rainfall can reach 7.4 in. May is typically the driest time to visit Pensacola when rainfall is around 4.2 in.

Temperature in Pensacola by month

Plan your trip to Pensacola by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Pensacola, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 March 28, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Chicago to Pensacola to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

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
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

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
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

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
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

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
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

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
7,882 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

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.

  • What are the cheapest airlines flying from Chicago to Pensacola round-trip?

    Cheapflights users have booked flights from Chicago to Pensacola round-trip from $185. Other airlines that can offer you cheap pricing are United Airlines, from $213, and Delta, from $217. Spirit Airlines is priced at 50% 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?

    $73 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 United Airlines and Frontier, with prices starting from $99 and $105, 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 (74%), Air New Zealand (68%), SkyWest Airlines( 50%).

  • What are the cheapest flights from Chicago to Pensacola?

    Looking at all options, your cheapest flight can be booked for $69. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $146 on average our data indicates $313 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 $306). Flying from Chicago to Pensacola in March is currently the most expensive (average of $418). 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
Gulf Breeze
Navarre
Foley
Perdido Key
Milton
Atmore
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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$204Average$321FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$214Average$327FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$222Average$394FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$240Average$418FlexibilityNo cancel feeOn-time69%
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