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Pensacola Beach

$47+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Pensacola Beach 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 Beach

Keep the following information in mind while searching for Chicago to Pensacola Beach flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Mytrip)

One-way from

$47
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$341
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 Beach
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One-way flight from Chicago (CHI) to Pensacola Beach
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 3/95:55 amORD - PNS
2 stops32h 27mSpirit Airlines
Sat 3/151:49 pmPNS - ORD
2 stops17h 55mSpirit Airlines
Deal found 2/20$217
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1212:20 pmMDW - PNS
1 stop3h 45mSouthwest
Wed 4/1611:30 amPNS - MDW
1 stop5h 35mSouthwest
Deal found 2/20$217
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/127:00 amORD - PNS
2 stops12h 30mSouthwest
Wed 4/163:05 pmPNS - ORD
1 stop6h 25mSouthwest
Deal found 2/20$222
This United Airlines deal was found by Cheapflights users on 2/19. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/511:07 amORD - PNS
Nonstop2h 24mUnited Airlines
Tue 4/156:30 amPNS - ORD
1 stop5h 50mUnited Airlines
Deal found 2/19$228
This Delta deal was found by Cheapflights users on 2/19. 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 8/2310:10 amMDW - PNS
1 stop4h 14mDelta
Sat 8/301:59 pmPNS - MDW
1 stop4h 04mDelta
Deal found 2/19$229
This CheapOair deal was found by Cheapflights users on 2/19. 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 4/46:45 amMDW - PNS
1 stop11h 38mFrontier
Fri 4/117:23 pmPNS - MDW
1 stop28h 58mFrontier
Deal found 2/19$230
This Mytrip deal was found by Cheapflights users on 2/20. 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 2/246:50 amORD - PNS
1 stop11h 37mFrontier
Thu 2/277:27 pmPNS - ORD
1 stop29h 17mFrontier
Deal found 2/20$231
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Thu 3/65:10 amORD - PNS
1 stop11h 55mMultiple Airlines
Sun 3/94:25 pmPNS - ORD
1 stop17h 03mMultiple Airlines
Deal found 2/19$233
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/47:05 amORD - PNS
1 stop4h 56mDelta
Sat 5/106:00 amPNS - ORD
1 stop4h 02mDelta
Deal found 2/20$239
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/144:40 pmORD - PNS
1 stop4h 35mAmerican Airlines
Sat 3/226:15 amPNS - ORD
1 stop7h 03mAmerican Airlines
Deal found 2/20$257

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 February 20, 2025.

Fly from

Chicago

Fly to

Pensacola Beach

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 3/9

5:55 am-2:22 pm

2 stops32h 27m

Pensacola

Sat 3/15

1:49 pm-7:44 am

2 stops17h 55m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 3/12

12:20 pm-4:05 pm

1 stop3h 45m

Pensacola

Wed 4/16

11:30 am-5:05 pm

1 stop5h 35m

$217

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 3/12

7:00 am-7:30 pm

2 stops12h 30m

Pensacola

Wed 4/16

3:05 pm-9:30 pm

1 stop6h 25m

$222

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 3/5

11:07 am-1:31 pm

Nonstop2h 24m

Pensacola

Tue 4/15

6:30 am-12:20 pm

1 stop5h 50m

$228

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 4/4

6:45 am-6:23 pm

1 stop11h 38m

Pensacola

Fri 4/11

7:23 pm-12:21 am

1 stop28h 58m

$230

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 2/24

6:50 am-6:27 pm

1 stop11h 37m

Pensacola

Thu 2/27

7:27 pm-12:44 am

1 stop29h 17m

$231

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 3/6

5:10 am-5:05 pm

1 stop11h 55m

Pensacola

Sun 3/9

4:25 pm-9:28 am

1 stop17h 03m

$233

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 5/4

7:05 am-12:01 pm

1 stop4h 56m

Pensacola

Sat 5/10

6:00 am-10:02 am

1 stop4h 02m

$239

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 3/7

6:00 am-11:26 am

1 stop5h 26m

Pensacola

Tue 3/11

7:05 am-12:06 pm

1 stop5h 01m

$239

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 3/14

4:40 pm-9:15 pm

1 stop4h 35m

Pensacola

Sat 3/22

6:15 am-1:18 pm

1 stop7h 03m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Pensacola Beach, you should look to book at least 62 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 $306). Flying from Chicago to Pensacola Beach 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 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 February 20, 2025.

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 February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines 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
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

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.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

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.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

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 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?

    $47 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 Frontier and United Airlines, with prices starting from $81 and $99, respectively.

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

    Consider SkyWest Airlines (100%), United Airlines (87%) 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 $355 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $133 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $96.

  • 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 $306). Flying from Chicago to Pensacola Beach 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.

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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 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$205FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$114Average$175FlexibilityNo cancel feeOn-time88%
DeltaCheapest$199Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$207Average$372FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$228Average$422FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$229Average$447FlexibilityNo cancel feeOn-time69%
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