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Pensacola Beach

$91+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 16 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 September 17, 2025.

Round-trip from

$203
(United Airlines)

One-way from

$91
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$304
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 September 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 September 17, 2025.

This United Airlines deal was found by Cheapflights users on 9/15. 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 10/1410:50 amORD - PNS
Nonstop2h 25mUnited Airlines
Fri 10/172:17 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Deal found 9/15$203
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Wed 10/16:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Sat 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/16$205
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Fri 10/176:00 amORD - PNS
1 stop11h 30mSpirit Airlines
Mon 10/274:36 pmPNS - ORD
1 stop8h 27mSpirit Airlines
Deal found 9/15$206
This CheapOair deal was found by Cheapflights users on 9/16. 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 10/165:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Sun 10/194:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/16$209
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sun 10/125:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Sun 10/194:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/14$211
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Sat 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/14$214
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:00 amORD - PNS
1 stop10h 26mFrontier
Sun 10/55:21 pmPNS - ORD
1 stop6h 38mFrontier
Deal found 9/16$215
This Delta deal was found by Cheapflights users on 9/15. 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 10/211:26 pmORD - PNS
1 stop5h 51mDelta
Wed 10/297:00 amPNS - ORD
1 stop5h 16mDelta
Deal found 9/15$217
This Southwest deal was found by Cheapflights users on 9/16. 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 10/148:40 amMDW - PNS
1 stop6h 50mSouthwest
Wed 10/221:25 pmPNS - MDW
1 stop5h 40mSouthwest
Deal found 9/16$217
This Southwest deal was found by Cheapflights users on 9/15. 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 11/1910:50 amMDW - PNS
1 stop4h 45mSouthwest
Wed 11/269:50 amPNS - MDW
1 stop7h 00mSouthwest
Deal found 9/15$218
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/1910:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Sun 11/232:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 9/15$219
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/319:32 amMDW - PNS
1 stop7h 58mMultiple Airlines
Sun 11/24:30 pmPNS - MDW
1 stop19h 00mMultiple Airlines
Deal found 9/14$219

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 September 17, 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

MDW - PNS

MDWPNS

Chicago Midway

Tue 10/14

8:40 am-3:30 pm

1 stop6h 50m

Pensacola

Wed 10/22

1:25 pm-7:05 pm

1 stop5h 40m

$217

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 10/21

1:26 pm-7:17 pm

1 stop5h 51m

Pensacola

Wed 10/29

7:00 am-12:16 pm

1 stop5h 16m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 12/2

5:35 am-9:20 am

1 stop3h 45m

Pensacola

Wed 12/3

4:15 pm-8:15 pm

1 stop4h 00m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/19

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Wed 11/26

9:50 am-4:50 pm

1 stop7h 00m

$218

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/5

6:00 am-10:42 am

1 stop4h 42m

Pensacola

Sun 11/9

7:09 pm-11:32 pm

1 stop4h 23m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 12/2

5:32 pm-11:06 pm

1 stop5h 34m

Pensacola

Sun 12/14

6:00 am-9:54 am

1 stop3h 54m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 10/14

7:55 am-1:45 pm

1 stop5h 50m

Pensacola

Fri 10/17

7:35 pm-11:15 pm

1 stop3h 40m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 2/18

5:50 am-10:49 am

1 stop4h 59m

Pensacola

Sat 2/21

5:00 pm-11:54 pm

1 stop6h 54m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 10/26

5:35 am-9:10 am

1 stop3h 35m

Pensacola

Wed 10/29

2:30 pm-6:10 pm

1 stop3h 40m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 10/24

1:30 pm-6:50 pm

1 stop5h 20m

Pensacola

Wed 10/29

7:40 am-12:45 pm

1 stop5h 05m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 40 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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Pensacola Beach, you should look to book at least 16 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 $302). Flying from Chicago to Pensacola Beach in March is currently the most expensive (average of $415). 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 September 17, 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.

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 September 17, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago to Pensacola Beach have to say. 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
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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.

  • How long is the flight from Chicago to Pensacola Beach?

    Airlines like Southwest and Delta fly from Chicago to Pensacola Beach in about 5h 51m. The time it takes to get you to your destination can typically vary by up to 59m. There are 795 mi between Chicago and Pensacola Beach. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $99 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $104 and $109, respectively.

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

    Consider United Airlines (87%), Air New Zealand (87%) or American Airlines (67%) 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 $368 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $107 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $182.

  • 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 $302). Flying from Chicago to Pensacola Beach in March is currently the most expensive (average of $415). 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

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$138FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$399FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$225Average$395FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$416FlexibilityNo cancel feeOn-time69%

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