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Pensacola

$79+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pensacola are usually found in January or April, booked 84 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 July 31, 2025.

Round-trip from

$240
(United Airlines)

One-way from

$79
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$376

Good round-trip deal

$293 or less

Good one-way deal

$138 or less
From Chicago (CHI) to Pensacola
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One-way flight from Chicago (CHI) to Pensacola
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High demand for flights, 0% potential price rise
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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 July 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 July 31, 2025.

This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2510:50 amORD - PNS
Nonstop2h 25mUnited Airlines
Tue 9/302:17 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Deal found 7/29$240
This Mytrip deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/138:12 pmORD - PNS
2 stops20h 55mSpirit Airlines
Sat 8/169:14 amPNS - ORD
1 stop9h 53mSpirit Airlines
Deal found 7/30$241
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/187:50 amMDW - PNS
1 stop6h 45mSouthwest
Mon 9/2210:00 amPNS - MDW
2 stops7h 45mSouthwest
Deal found 7/31$242
This Southwest deal was found by Cheapflights users on 7/30. 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 9/233:10 pmORD - PNS
1 stop3h 45mSouthwest
Tue 9/307:35 amPNS - ORD
2 stops10h 20mSouthwest
Deal found 7/30$242
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/124:48 pmMDW - PNS
1 stop23h 38mFrontier
Sun 9/145:21 pmPNS - MDW
1 stop22h 32mFrontier
Deal found 7/30$245
This American Airlines deal was found by Cheapflights users on 7/31. 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 11/510:30 amORD - PNS
Nonstop2h 30mAmerican Airlines
Tue 11/116:00 amPNS - ORD
1 stop6h 07mAmerican Airlines
Deal found 7/31$246
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/27:00 amORD - PNS
1 stop8h 34mMultiple Airlines
Sat 8/96:00 amPNS - ORD
1 stop10h 57mMultiple Airlines
Deal found 7/29$253
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 9/116:00 amMDW - PNS
1 stop4h 50mDelta
Wed 9/175:00 pmPNS - MDW
1 stop4h 36mDelta
Deal found 7/30$260
This Delta deal was found by Cheapflights users on 7/30. 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.
Mon 9/155:30 amORD - PNS
1 stop5h 20mDelta
Sat 9/206:00 amPNS - ORD
1 stop4h 10mDelta
Deal found 7/30$260
This Frontier deal was found by Cheapflights users on 7/30. 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 9/126:00 amORD - PNS
1 stop10h 26mFrontier
Sun 9/145:21 pmPNS - ORD
1 stop6h 38mFrontier
Deal found 7/30$268

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 July 31, 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 9/25

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Tue 9/30

2:17 pm-4:54 pm

Nonstop2h 37m

$240

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 8/13

8:12 pm-5:07 pm

2 stops20h 55m

Pensacola

Sat 8/16

9:14 am-7:07 pm

1 stop9h 53m

$241

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 9/18

7:50 am-2:35 pm

1 stop6h 45m

Pensacola

Mon 9/22

10:00 am-5:45 pm

2 stops7h 45m

$242

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 9/23

3:10 pm-6:55 pm

1 stop3h 45m

Pensacola

Tue 9/30

7:35 am-5:55 pm

2 stops10h 20m

$242

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 9/12

4:48 pm-4:26 pm

1 stop23h 38m

Pensacola

Sun 9/14

5:21 pm-3:53 pm

1 stop22h 32m

$245

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 9/11

6:00 am-10:50 am

1 stop4h 50m

Pensacola

Wed 9/17

5:00 pm-9:36 pm

1 stop4h 36m

$260

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 9/15

5:30 am-10:50 am

1 stop5h 20m

Pensacola

Sat 9/20

6:00 am-10:10 am

1 stop4h 10m

$260

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 9/12

6:00 am-4:26 pm

1 stop10h 26m

Pensacola

Fri 9/19

5:21 pm-11:59 pm

1 stop6h 38m

$268

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 9/9

6:30 am-6:10 pm

1 stop11h 40m

$79

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 9/27

8:20 am-10:30 am

Nonstop2h 10m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 17 results
1
2

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 July 25, 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 84 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 $417). 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 July 31, 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 27% 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 July 27, 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 July 31, 2025.

The most flights from CHI to PNS are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, 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.

Nashville (BNA) – chosen by Cheapflights users on 33% 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.

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $281.

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 Nashville (BNA) have the shortest average one-way travel time for 1-stop routes: 3h 55m.

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 Fort Lauderdale (FLL) offer the fastest connection on this route, with an average layover time of 1h 10m.

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 July 31, 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
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

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
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

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
8,049 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

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.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

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.

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

    Cheapflights users have booked flights from Chicago to Pensacola round-trip from $240. Other airlines that can offer you cheap pricing are Spirit Airlines, from $241, and Southwest, from $242. United Airlines is priced at 31% 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?

    $79 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 Southwest, with prices starting from $109 and $109, 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%), Envoy Air( 83%).

  • What are the cheapest flights from Chicago to Pensacola?

    Looking at all options, your cheapest flight can be booked for $166. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $171 on average our data indicates $332 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 $417). 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
Milton
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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$314FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$377FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$322FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$235Average$405FlexibilityNo cancel feeOn-time69%

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