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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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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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 Thursday

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 November 20, 2024.

Popular in

March

Cheapest in

January

Round-trip from

$233
(United Airlines)

One-way from

$60
(Frontier)
High demand for flights, 17% potential price rise
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Best time to find cheap flights, 26% potential price drop
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From Chicago (CHI) to Pensacola Beach
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One-way flight from Chicago (CHI) to Pensacola Beach
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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 November 20, 2024.

This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sat 12/77:33 amORD - PNS
2 stops10h 32mSpirit Airlines
Sat 12/145:15 pmPNS - ORD
1 stop16h 22mSpirit Airlines
Deal found 11/19$234
This Delta deal was found by Cheapflights users on 11/19. 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 12/75:55 pmORD - PNS
1 stop5h 15mDelta
Sat 12/145:37 pmPNS - ORD
1 stop6h 21mDelta
Deal found 11/19$238
This Mytrip deal was found by Cheapflights users on 11/20. 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 12/308:14 pmORD - PNS
2 stops19h 55mMultiple Airlines
Sun 1/54:22 pmPNS - ORD
1 stop15h 25mMultiple Airlines
Deal found 11/20$254
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Thu 12/57:15 amMDW - PNS
1 stop10h 58mFrontier
Sun 12/87:17 pmPNS - MDW
1 stop28h 56mFrontier
Deal found 11/20$258
This CheapOair deal was found by Cheapflights users on 11/19. 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 12/67:25 amORD - PNS
1 stop10h 57mFrontier
Sun 12/87:17 pmPNS - ORD
1 stop18h 43mFrontier
Deal found 11/19$274
This United deal was found by Cheapflights users on 11/19. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1610:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Mon 12/232:21 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Deal found 11/19$279
This Delta deal was found by Cheapflights users on 11/19. 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 12/116:00 amMDW - PNS
1 stop4h 06mDelta
Fri 12/135:47 pmPNS - MDW
1 stop4h 19mDelta
Deal found 11/19$303
This eDestinos deal was found by Cheapflights users on 11/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/268:50 amMDW - PNS
3 stops46h 54mMultiple Airlines
Tue 12/37:10 pmPNS - MDW
2 stops16h 32mMultiple Airlines
Deal found 11/18$339
This Southwest deal was found by Cheapflights users on 11/19. 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.
Fri 12/68:40 amMDW - PNS
2 stops10h 10mSouthwest
Sun 12/89:50 amPNS - MDW
1 stop6h 25mSouthwest
Deal found 11/19$353
This Southwest deal was found by Cheapflights users on 11/19. 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 12/257:30 amORD - PNS
2 stops8h 20mSouthwest
Wed 1/18:45 amPNS - ORD
1 stop4h 15mSouthwest
Deal found 11/19$376

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 2/18

11:07 am-1:31 pm

Nonstop2h 24m

Pensacola

Mon 2/24

2:33 pm-5:10 pm

Nonstop2h 37m

$233

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 12/7

7:33 am-6:05 pm

2 stops10h 32m

Pensacola

Sat 12/14

5:15 pm-9:37 am

1 stop16h 22m

$234

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 3/18

9:30 am-2:27 pm

1 stop4h 57m

Pensacola

Tue 4/1

12:38 pm-8:53 pm

1 stop8h 15m

$238

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/3

6:00 am-11:02 am

1 stop5h 02m

Pensacola

Fri 1/3

5:42 pm-10:06 pm

1 stop4h 24m

$238

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 12/30

8:14 pm-4:09 pm

2 stops19h 55m

Pensacola

Sun 1/5

4:22 pm-7:47 am

1 stop15h 25m

$254

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 12/5

7:15 am-6:13 pm

1 stop10h 58m

Pensacola

Sun 12/8

7:17 pm-12:13 am

1 stop28h 56m

$258

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 2/10

7:30 am-3:05 pm

2 stops7h 35m

Pensacola

Sun 2/16

7:35 am-1:00 pm

1 stop5h 25m

$267

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 12/6

7:25 am-6:22 pm

1 stop10h 57m

Pensacola

Sun 12/8

7:17 pm-2:00 pm

1 stop18h 43m

$274

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 12/31

2:55 pm-11:53 pm

1 stop8h 58m

Pensacola

Wed 1/1

5:30 am-11:03 am

1 stop5h 33m

$283

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/12

6:25 am-11:00 am

1 stop4h 35m

Pensacola

Sun 2/16

6:05 pm-12:25 am

1 stop6h 20m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 22 results
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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 November 15, 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 $379). 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 November 20, 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 November 18, 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 November 20, 2024.
Read reviews from past customers who have flown United Airlines, Southwest and American Airlines 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
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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.

Spirit Airlines
6.3
Okay
8,174 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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?

    $60 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 $81 and $105, respectively.

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

    Consider SkyWest Airlines (95%), United Airlines (93%) or Air New Zealand (93%) 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 $364 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $159 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $165.

  • 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 $379). 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.

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Alternative routes for Chicago to Pensacola Beach

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$174FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$100Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$143Average$418FlexibilityNo cancel feeOn-time63%
DeltaCheapest$199Average$370FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$362FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$231Average$441FlexibilityNo cancel feeOn-time69%
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