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Pensacola

$64+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This CheapOair deal was found by Cheapflights users on 1/27. 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.
Sat 2/710:48 am
ORD
-
PNS
1 stop5h 49m
Spirit Airlines
Sat 2/145:20 pm
PNS
-
ORD
1 stop6h 27m
Spirit Airlines
Deal found 1/27$215
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 2/257:00 am
MDW
-
PNS
2 stops34h 42m
Multiple Airlines
Wed 3/46:37 pm
PNS
-
MDW
1 stop19h 49m
Multiple Airlines
Deal found 1/28$215
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 3/138:41 pm
ORD
-
PNS
2 stops24h 33m
Multiple Airlines
Wed 3/187:00 am
PNS
-
ORD
1 stop16h 38m
Multiple Airlines
Deal found 1/28$216
This Mytrip deal was found by Cheapflights users on 1/28. 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.
Fri 3/65:58 pm
ORD
-
PNS
2 stops23h 44m
Spirit Airlines
Mon 3/95:20 pm
PNS
-
ORD
1 stop6h 27m
Spirit Airlines
Deal found 1/28$217
This Southwest deal was found by Cheapflights users on 1/27. 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.
Wed 3/46:00 am
MDW
-
PNS
1 stop3h 50m
Southwest
Tue 3/105:20 pm
PNS
-
MDW
Nonstop2h 15m
Southwest
Deal found 1/27$217
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 2/2310:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Tue 2/246:37 pm
PNS
-
ORD
2 stops16h 45m
Spirit Airlines
Deal found 1/28$218
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:07 pm
ORD
-
PNS
1 stop20h 35m
Multiple Airlines
Tue 2/246:37 pm
PNS
-
ORD
2 stops16h 45m
Multiple Airlines
Deal found 1/27$219
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 2/2310:44 am
ORD
-
PNS
1 stop6h 58m
Multiple Airlines
Sat 2/2811:18 am
PNS
-
ORD
2 stops13h 22m
Multiple Airlines
Deal found 1/28$220
This Mytrip deal was found by Cheapflights users on 1/27. 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 3/510:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Tue 3/106:37 pm
PNS
-
ORD
2 stops24h 34m
Spirit Airlines
Deal found 1/27$221
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:30 am
MDW
-
PNS
2 stops32h 24m
Multiple Airlines
Fri 2/276:37 pm
PNS
-
MDW
1 stop20h 18m
Multiple Airlines
Deal found 1/27$221
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 4/99:30 am
ORD
-
PNS
1 stop11h 44m
Multiple Airlines
Tue 4/147:00 am
PNS
-
ORD
2 stops14h 17m
Multiple Airlines
Deal found 1/28$222
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Fri 5/85:15 am
ORD
-
PNS
1 stop7h 37m
Spirit Airlines
Mon 5/111:47 pm
PNS
-
ORD
1 stop9h 54m
Spirit Airlines
Deal found 1/27$223

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$215
(Kiwi.com)

One-way from

$64
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$353

Good round-trip deal

$294 or less

Good one-way deal

$194 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. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Sun 4/19

6:00 am-10:02 am

1 stop4h 02m

Pensacola

Wed 4/22

6:00 am-9:56 am

1 stop3h 56m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

6:40 pm-11:11 pm

1 stop4h 31m

Pensacola

Tue 2/24

6:00 am-11:59 am

1 stop5h 59m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 2/23

12:45 pm-6:19 pm

1 stop5h 34m

Pensacola

Tue 2/24

6:00 am-9:54 am

1 stop3h 54m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 2/22

6:00 am-10:31 am

1 stop4h 31m

Pensacola

Tue 2/24

4:04 pm-10:33 pm

1 stop6h 29m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 2/22

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Wed 2/25

6:00 am-11:59 am

1 stop5h 59m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/25

6:00 am-10:31 am

1 stop4h 31m

Pensacola

Wed 2/25

5:48 pm-10:31 pm

1 stop4h 43m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 3/11

6:00 am-10:06 am

1 stop4h 06m

Pensacola

Sun 3/15

6:00 am-9:56 am

1 stop3h 56m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 3/8

6:00 am-10:06 am

1 stop4h 06m

Pensacola

Wed 3/11

6:00 am-9:56 am

1 stop3h 56m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 2/24

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Wed 2/25

6:00 am-9:54 am

1 stop3h 54m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 3/2

10:49 am-2:54 pm

1 stop4h 05m

Pensacola

Thu 3/5

6:00 am-9:54 am

1 stop3h 54m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 48 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 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 January 23, 2026.

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 August is currently the most expensive (average of $217). 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 January 29, 2026.

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 32% on airfare.

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 January 29, 2026.

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

How much does it cost to fly round-trip from Chicago to Pensacola?

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 January 29, 2026.
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
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
8,393 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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?

    Delta can get you from Chicago to Pensacola in just under 4h 02m. Your travel time can differ by up to . Chicago and Pensacola are separated by a distance of 782 mi.

  • 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 $154, and United Airlines, from $209. 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?

    $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 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 (80%), Air New Zealand (80%), Republic Airways( 67%).

  • What are the cheapest flights from Chicago to Pensacola?

    Looking at all options, your cheapest flight can be booked for $159. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $147 on average, our data indicates $494 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 $217). 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
Navarre Beach
Perdido Key
Warrington

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Alternative routes for Chicago to Pensacola

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$154Average$282FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$370FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$321FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$214Average$355FlexibilityNo cancel feeOn-time63%

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