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Pensacola Beach

$79+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pensacola Beach 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 Beach

Keep the following information in mind while searching for Chicago to Pensacola Beach flight deals. Data was last updated June 12, 2025.

Round-trip from

$214
(Delta)

One-way from

$79
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$369
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. 0% potential increase in price ($1 potential increase over avg. RT price).
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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 June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 10/147:10 amORD - PNS
1 stop5h 40mDelta
Sat 10/185:45 pmPNS - ORD
1 stop6h 08mDelta
Deal found 6/10$214
This Southwest deal was found by Cheapflights users on 6/9. 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.
Sat 9/68:15 amMDW - PNS
1 stop6h 50mSouthwest
Mon 9/84:35 pmPNS - MDW
1 stop6h 15mSouthwest
Deal found 6/9$214
This FlightHub deal was found by Cheapflights users on 6/11. 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 8/227:00 pmORD - PNS
1 stop14h 00mSpirit Airlines
Mon 8/2510:08 amPNS - ORD
1 stop7h 42mSpirit Airlines
Deal found 6/11$215
This United Airlines deal was found by Cheapflights users on 6/11. 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 8/510:39 amORD - PNS
Nonstop2h 27mUnited Airlines
Thu 8/72:08 pmPNS - ORD
Nonstop2h 39mUnited Airlines
Deal found 6/11$227
This Delta deal was found by Cheapflights users on 6/12. 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 9/296:00 amMDW - PNS
1 stop4h 46mDelta
Tue 10/77:00 amPNS - MDW
2 stops11h 36mDelta
Deal found 6/12$236
This Southwest deal was found by Cheapflights users on 6/10. 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 8/11:30 pmORD - PNS
1 stop6h 10mSouthwest
Mon 8/46:00 amPNS - ORD
2 stops11h 55mSouthwest
Deal found 6/10$242
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 10/165:00 amORD - PNS
1 stop7h 14mAmerican Airlines
Mon 10/272:30 pmPNS - ORD
1 stop8h 21mAmerican Airlines
Deal found 6/11$251
This FlightHub deal was found by Cheapflights users on 6/9. 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.
Tue 6/1710:46 amORD - PNS
1 stop11h 51mMultiple Airlines
Fri 6/204:29 pmPNS - ORD
1 stop7h 30mMultiple Airlines
Deal found 6/9$252
This Mytrip deal was found by Cheapflights users on 6/10. 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 8/111:11 pmMDW - PNS
2 stops23h 37mMultiple Airlines
Thu 8/143:50 pmPNS - MDW
2 stops26h 27mMultiple Airlines
Deal found 6/10$308
This Frontier deal was found by Cheapflights users on 6/10. 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.
Sat 10/117:20 amORD - PNS
1 stop8h 11mFrontier
Thu 10/164:35 pmPNS - ORD
1 stop7h 18mFrontier
Deal found 6/10$374
This Booking.com deal was found by Cheapflights users on 6/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/122:44 pmMDW - PNS
1 stop24h 45mFrontier
Sat 6/144:29 pmPNS - MDW
1 stop28h 24mFrontier
Deal found 6/9$384

Cheapflights Fare Finder

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 June 12, 2025.
Use the filters below to find and compare flights from Chicago to Pensacola Beach that are best for you.

Fly from

Chicago

Fly to

Pensacola Beach

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 10/14

7:10 am-12:50 pm

1 stop5h 40m

Pensacola

Sat 10/18

5:45 pm-11:53 pm

1 stop6h 08m

$214

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 9/6

8:15 am-3:05 pm

1 stop6h 50m

Pensacola

Mon 9/8

4:35 pm-10:50 pm

1 stop6h 15m

$214

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 8/22

7:00 pm-9:00 am

1 stop14h 00m

Pensacola

Mon 8/25

10:08 am-5:50 pm

1 stop7h 42m

$215

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 8/5

10:39 am-1:06 pm

Nonstop2h 27m

Pensacola

Tue 8/12

2:08 pm-4:47 pm

Nonstop2h 39m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 9/29

6:00 am-10:46 am

1 stop4h 46m

Pensacola

Wed 10/8

6:00 am-6:36 pm

2 stops12h 36m

$236

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 8/1

1:30 pm-7:40 pm

1 stop6h 10m

Pensacola

Mon 8/4

6:00 am-5:55 pm

2 stops11h 55m

$242

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 10/16

5:00 am-12:14 pm

1 stop7h 14m

Pensacola

Mon 10/27

2:30 pm-10:51 pm

1 stop8h 21m

$251

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 10/10

6:00 am-3:31 pm

1 stop9h 31m

Pensacola

Mon 10/20

8:46 am-5:37 pm

1 stop8h 51m

$308

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 8/11

1:11 pm-12:48 pm

2 stops23h 37m

Pensacola

Thu 8/14

3:50 pm-6:17 pm

2 stops26h 27m

$308

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 9/29

6:00 am-3:31 pm

1 stop9h 31m

Pensacola

Thu 10/9

4:35 pm-11:53 pm

1 stop7h 18m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Pensacola Beach

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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Pensacola Beach, you should look to book at least 84 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 June 12, 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. 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 Beach

Explore weekly flight availability from Chicago to Pensacola Beach. 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 June 12, 2025.

The most flights from CHI to PB9 are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and United 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
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8,052 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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?

    $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 Delta and Southwest, with prices starting from $89 and $89, respectively.

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

    Consider Spirit Airlines (100%), United Airlines (90%) or Air New Zealand (90%) 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 $312 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $88 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $166.

  • 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$92Average$180FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$339FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$222Average$369FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$237Average$504FlexibilityNo cancel feeOn-time69%

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