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Pensacola Beach

$69+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$166
(Cheapflightsfares)

One-way from

$69
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$375
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. 2% potential increase in price ($10 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Tue 5/135:05 amORD - PNS
1 stop10h 25mSpirit Airlines
Sat 5/176:14 pmPNS - ORD
1 stop5h 15mSpirit Airlines
Deal found 4/29$166
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/1310:40 amORD - PNS
Nonstop2h 28mUnited Airlines
Sat 5/172:05 pmPNS - ORD
Nonstop2h 41mUnited Airlines
Deal found 4/29$177
This Southwest deal was found by Cheapflights users on 4/29. 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 5/136:45 amMDW - PNS
1 stop4h 00mSouthwest
Sat 5/174:15 pmPNS - MDW
Nonstop2h 10mSouthwest
Deal found 4/29$187
This Delta deal was found by Cheapflights users on 4/30. 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 6/146:15 pmORD - PNS
1 stop5h 05mDelta
Wed 6/186:00 amPNS - ORD
1 stop4h 09mDelta
Deal found 4/30$197
This Delta deal was found by Cheapflights users on 4/30. 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 6/74:15 pmMDW - PNS
1 stop5h 21mDelta
Mon 6/164:07 pmPNS - MDW
1 stop5h 38mDelta
Deal found 4/30$197
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 5/188:15 amORD - PNS
Nonstop2h 24mAmerican Airlines
Sun 5/2512:07 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 4/30$203
This Southwest deal was found by Cheapflights users on 4/30. 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 5/281:50 pmORD - PNS
2 stops8h 20mSouthwest
Wed 6/48:00 amPNS - ORD
1 stop4h 45mSouthwest
Deal found 4/30$252
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/811:45 amORD - PNS
2 stops19h 40mMultiple Airlines
Sat 5/106:14 pmPNS - ORD
1 stop5h 15mMultiple Airlines
Deal found 4/30$283
This Frontier deal was found by Cheapflights users on 4/30. 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.
Fri 5/306:00 amORD - PNS
1 stop9h 23mFrontier
Mon 6/24:29 pmPNS - ORD
1 stop7h 30mFrontier
Deal found 4/30$290
This Gotogate deal was found by Cheapflights users on 4/30. 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.
Fri 6/1312:35 pmMDW - PNS
1 stop26h 54mFrontier
Fri 6/204:29 pmPNS - MDW
1 stop28h 24mFrontier
Deal found 4/30$436

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 May 1, 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 5/13

5:05 am-3:30 pm

1 stop10h 25m

Pensacola

Sat 5/17

6:14 pm-11:29 pm

1 stop5h 15m

$166

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 5/13

10:40 am-1:08 pm

Nonstop2h 28m

Pensacola

Sat 5/17

2:05 pm-4:46 pm

Nonstop2h 41m

$177

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 5/13

6:45 am-10:45 am

1 stop4h 00m

Pensacola

Sat 5/17

4:15 pm-6:25 pm

Nonstop2h 10m

$187

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 6/14

6:15 pm-11:20 pm

1 stop5h 05m

Pensacola

Wed 6/18

6:00 am-10:09 am

1 stop4h 09m

$197

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 6/7

4:15 pm-9:36 pm

1 stop5h 21m

Pensacola

Mon 6/16

4:07 pm-9:45 pm

1 stop5h 38m

$197

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 5/18

8:15 am-10:39 am

Nonstop2h 24m

Pensacola

Sun 5/25

12:07 pm-2:49 pm

Nonstop2h 42m

$203

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 5/28

1:50 pm-10:10 pm

2 stops8h 20m

Pensacola

Wed 6/4

8:00 am-12:45 pm

1 stop4h 45m

$252

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 5/8

11:45 am-7:25 am

2 stops19h 40m

Pensacola

Sat 5/10

6:14 pm-11:29 pm

1 stop5h 15m

$283

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 5/30

6:00 am-3:23 pm

1 stop9h 23m

Pensacola

Mon 6/2

4:29 pm-11:59 pm

1 stop7h 30m

$290

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 6/13

12:35 pm-3:29 pm

1 stop26h 54m

Pensacola

Fri 6/20

4:29 pm-8:53 pm

1 stop28h 24m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 21 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 April 25, 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 May 1, 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.

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 May 1, 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
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

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
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

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
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

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
7,962 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

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 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?

    $69 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 American Airlines and Southwest, with prices starting from $89 and $89, respectively.

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

    Consider American Airlines (100%), Envoy Air (100%) or Spirit Airlines (89%) 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 $315 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $104 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 $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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$92Average$167FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$205FlexibilityNo cancel feeOn-time65%
DeltaCheapest$199Average$333FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$383FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$430FlexibilityNo cancel feeOn-time69%

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