HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pensacola Beach

$54+ Cheap flights from Chicago (CHI) to Pensacola Beach, FL

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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Pensacola Beach 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chicago to Pensacola Beach are usually found in January or April, booked 63 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Chicago to Pensacola Beach

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pensacola Beach (PB9). 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 18, 2024.

Round-trip from

$228
(American Airlines)

One-way from

$54
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$444
From Chicago (CHI) to Pensacola Beach
Search Deals
One-way flight from Chicago (CHI) to Pensacola Beach
Search Deals
High demand for flights, 1% potential price rise
Search Deals
Best time to find cheap flights, 1% potential price drop
Search Deals
Average for round-trip flights in December 2024
Search Deals

Find flight deals from Chicago to Pensacola Beach

Cheapest flights from Chicago to Pensacola Beach
Explore the most affordable flight options available from Chicago to Pensacola Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2024.

This CheapOair deal was found by Cheapflights users on 12/17. 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.
Tue 12/313:31 pmORD - PNS
1 stop26h 34mSpirit Airlines
Tue 1/77:07 pmPNS - ORD
1 stop24h 44mSpirit Airlines
Deal found 12/17$246
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/2010:05 amORD - PNS
1 stop7h 20mAmerican Airlines
Wed 1/16:00 amPNS - ORD
1 stop8h 00mAmerican Airlines
Deal found 12/18$333
This Mytrip deal was found by Cheapflights users on 12/17. 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 12/307:30 pmORD - PNS
2 stops22h 35mMultiple Airlines
Mon 1/67:00 pmPNS - ORD
3 stops29h 33mMultiple Airlines
Deal found 12/17$344
This Southwest deal was found by Cheapflights users on 12/17. 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 12/316:20 amMDW - PNS
1 stop3h 40mSouthwest
Tue 1/711:40 amPNS - MDW
1 stop8h 15mSouthwest
Deal found 12/17$344
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/3110:50 amORD - PNS
Nonstop2h 30mUnited Airlines
Tue 1/72:31 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Deal found 12/17$369
This Southwest deal was found by Cheapflights users on 12/17. 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 12/315:45 amORD - PNS
2 stops13h 05mSouthwest
Mon 1/64:25 pmPNS - ORD
1 stop5h 35mSouthwest
Deal found 12/17$388
This Gotogate deal was found by Cheapflights users on 12/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:55 amORD - PNS
1 stop29h 00mFrontier
Fri 1/310:06 pmPNS - ORD
1 stop24h 38mFrontier
Deal found 12/17$524
This Delta deal was found by Cheapflights users on 12/17. 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.
Sat 12/283:20 pmORD - PNS
1 stop6h 09mDelta
Mon 12/307:12 pmPNS - ORD
1 stop4h 41mDelta
Deal found 12/17$628
This Delta deal was found by Cheapflights users on 12/18. 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.
Sun 12/226:00 amMDW - PNS
1 stop5h 02mDelta
Fri 12/275:40 pmPNS - MDW
1 stop4h 26mDelta
Deal found 12/18$668
This CheapOair deal was found by Cheapflights users on 12/17. 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 12/278:27 pmMDW - PNS
1 stop24h 20mFrontier
Fri 1/310:06 pmPNS - MDW
1 stop15h 02mFrontier
Deal found 12/17$918

Find flights from Chicago to Pensacola Beach within your budget

Customize your flight search to find flights from Chicago to Pensacola Beach 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 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 1/16

5:10 am-10:33 am

1 stop5h 23m

Pensacola

Tue 1/21

5:30 am-12:30 pm

1 stop7h 00m

$228

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 1/21

10:57 am-4:58 pm

1 stop6h 01m

Pensacola

Tue 1/28

6:03 pm-10:20 pm

1 stop4h 17m

$228

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 1/6

10:50 am-1:20 pm

Nonstop2h 30m

Pensacola

Sun 1/12

4:55 pm-12:15 am

1 stop7h 20m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 1/6

5:11 pm-6:12 pm

1 stop25h 01m

Pensacola

Fri 1/10

10:19 am-11:32 pm

1 stop13h 13m

$230

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 2/27

5:45 am-9:57 am

1 stop4h 12m

Pensacola

Thu 3/6

6:03 pm-11:49 pm

1 stop5h 46m

$263

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 1/16

7:15 am-6:17 pm

1 stop11h 02m

Pensacola

Mon 1/20

7:17 pm-12:17 am

1 stop29h 00m

$268

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 1/6

7:30 am-6:50 pm

2 stops11h 20m

Pensacola

Sun 1/12

5:00 pm-10:20 pm

1 stop5h 20m

$293

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/15

7:20 am-1:10 pm

1 stop5h 50m

Pensacola

Sat 2/22

3:35 pm-11:15 pm

1 stop7h 40m

$293

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 1/1

3:31 pm-6:05 pm

1 stop26h 34m

Pensacola

Sun 1/5

8:21 pm-11:46 pm

1 stop27h 25m

$342

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 3/4

6:50 am-4:23 pm

1 stop9h 33m

$54

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 20 results
1
2

Best time to book a flight from Chicago to Pensacola Beach

Have a flexible travel schedule? Discover the best time to fly to Pensacola Beach 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.

Travel insights for flights from Chicago to Pensacola Beach

Get recent, data-driven insights about flights from Chicago to Pensacola Beach including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Pensacola Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Pensacola Beach. Price data was last updated on December 13, 2024.

To ensure you get the cheapest price possible for a flight from Chicago to Pensacola Beach, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Pensacola Beach?

Currently, September is the cheapest month in which you can book a flight from Chicago to Pensacola Beach (average of $296). Flying from Chicago to Pensacola Beach in March is currently the most expensive (average of $380). 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 PB9?

Find hourly flight availability from Chicago to Pensacola Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2024.

When flying from Chicago to Pensacola Beach, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Pensacola Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Pensacola Beach. Price data was last updated on December 16, 2024.

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

Rainfall in Pensacola Beach by month

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

In terms of precipitation, rainfall in Pensacola Beach 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 Beach when rainfall is around 4.2 in.

Temperature in Pensacola Beach by month

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

If weather is an important factor for your trip to Pensacola Beach, 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 Beach

Get insights into the airlines that provide service to Pensacola Beach. 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 Beach. Reviews last updated December 18, 2024.
Read reviews from past customers who have flown American Airlines, Frontier and Delta from Chicago to Pensacola Beach. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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.

Alaska Airlines
8.0
Very good
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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 Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Pensacola Beach one-way?

    $54 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $80 and $105, respectively.

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

    Consider SkyWest Airlines (92%), United Airlines (83%) or Air New Zealand (82%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Pensacola Beach.

  • What are the cheapest flights from Chicago to Pensacola Beach?

    On average you can expect to pay $363 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $139 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $146.

  • Can I find deals for flights from Chicago to Pensacola Beach that include hotel bookings?

    Yes. In addition to deals on Chicago to Pensacola Beach flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Pensacola Beach?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Pensacola Beach.

  • Can I find deals for business class flights from Chicago to Pensacola Beach?

    Yes. Cheapflights offers flight deals from Chicago to Pensacola Beach 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 Beach?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Pensacola Beach (average of $296). Flying from Chicago to Pensacola Beach in March is currently the most expensive (average of $380). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Pensacola Beach

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Midway to Miami flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to West Palm Beach flights
Midway to Tampa flights
O'Hare Intl to Key West flights
O'Hare Intl to Sarasota flights
Midway to Fort Lauderdale flights
O'Hare Intl to Jacksonville flights
St. Louis to Orlando flights
St. Louis to Miami flights
Midway to Fort Myers flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
O'Hare Intl to Panama City flights
St. Louis to Fort Lauderdale flights
Midway to Key West flights
Midway to Sarasota flights
St. Louis to Tampa flights
Rockford to Orlando Sanford Intl flights
Moline to Orlando flights
O'Hare Intl to Daytona Beach flights
O'Hare Intl to Valparaiso flights
St. Louis to Fort Myers flights
St. Louis to Sarasota flights
Midway to Pensacola flights
Moline to Tampa flights
Midway to Jacksonville flights
St. Louis to Key West flights
Midway to Panama City flights
O'Hare Intl to Melbourne flights
St. Louis to Jacksonville flights
Moline to Fort Myers flights
Rockford to St Petersburg flights
Peoria to Fort Myers flights
Peoria to Fort Lauderdale flights
Midway to Daytona Beach flights
Bloomington to Orlando flights
St. Louis to West Palm Beach flights
Peoria to Orlando flights
Peoria to Miami flights
St. Louis to Pensacola flights
Moline to Miami flights
Peoria to Tampa flights
Midway to Melbourne flights
Moline to Pensacola flights

Top 6 airlines flying from Chicago to Pensacola Beach

Discover the top 6 airlines that operate flights from Chicago to Pensacola Beach. 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 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$175FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$100Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$143Average$421FlexibilityNo cancel feeOn-time63%
DeltaCheapest$199Average$369FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$364FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$241Average$441FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.