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Pensacola Beach

$75+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pensacola Beach are usually found in September or November, booked 62 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap 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 December 21, 2025.

This Delta deal was found by Cheapflights users on 12/20. 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.
Wed 12/315:31 pmORD - PNS
1 stop4h 16mDelta
Wed 1/712:55 pmPNS - ORD
1 stop7h 52mDelta
Deal found 12/20$304
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:26 pmORD - PNS
1 stop26h 48mMultiple Airlines
Wed 1/711:18 amPNS - ORD
2 stops24h 17mMultiple Airlines
Deal found 12/20$329
This Delta deal was found by Cheapflights users on 12/20. 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.
Wed 12/316:35 amORD - PNS
2 stops15h 12mDelta
Tue 1/612:55 pmPNS - ORD
1 stop7h 52mDelta
Deal found 12/20$336
This American Airlines deal was found by Cheapflights users on 12/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:11 amORD - PNS
1 stop6h 52mAmerican Airlines
Mon 12/2911:29 amPNS - ORD
1 stop5h 48mAmerican Airlines
Deal found 12/18$339
This Delta deal was found by Cheapflights users on 12/19. 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.
Fri 12/265:29 pmORD - PNS
1 stop4h 18mDelta
Mon 1/55:54 pmPNS - ORD
1 stop6h 05mDelta
Deal found 12/19$344
This American Airlines deal was found by Cheapflights users on 12/20. 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.
Mon 12/295:21 amORD - PNS
1 stop5h 18mAmerican Airlines
Tue 1/66:00 amPNS - ORD
1 stop8h 01mAmerican Airlines
Deal found 12/20$353
This United Airlines deal was found by Cheapflights users on 12/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Thu 1/82:13 pmPNS - ORD
Nonstop2h 46mUnited Airlines
Deal found 12/20$354
This Southwest deal was found by Cheapflights users on 12/20. 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 12/315:35 amMDW - PNS
1 stop3h 45mSouthwest
Sat 1/31:10 pmPNS - MDW
2 stops6h 25mSouthwest
Deal found 12/20$354
This Delta deal was found by Cheapflights users on 12/19. 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.
Fri 12/265:05 pmMDW - PNS
1 stop4h 42mDelta
Mon 1/55:54 pmPNS - MDW
1 stop4h 13mDelta
Deal found 12/19$359
This American Airlines deal was found by Cheapflights users on 12/20. 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.
Mon 12/2210:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Sat 12/271:12 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 12/20$379
This Delta deal was found by Cheapflights users on 12/20. 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.
Mon 12/296:00 amMDW - PNS
1 stop5h 02mDelta
Fri 1/25:31 pmPNS - MDW
1 stop4h 51mDelta
Deal found 12/20$379
This American Airlines deal was found by Cheapflights users on 12/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:11 amORD - PNS
1 stop6h 52mAmerican Airlines
Thu 1/16:10 amPNS - ORD
1 stop7h 04mAmerican Airlines
Deal found 12/18$388

Find 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 December 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$75
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$354
Provider with most accurate pricing for Chicago (CHI)-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Pensacola flights.
Search Deals
From Chicago (CHI) to Pensacola Beach
Search Deals
One-way flight from Chicago (CHI) to Pensacola Beach
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 21, 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

Fri 1/30

5:30 am-10:26 am

1 stop4h 56m

Pensacola

Mon 2/2

12:55 pm-8:47 pm

1 stop7h 52m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/23

6:00 am-9:50 am

1 stop3h 50m

Pensacola

Sun 1/25

4:25 pm-10:30 pm

1 stop6h 05m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 1/31

5:30 am-10:26 am

1 stop4h 56m

Pensacola

Tue 2/3

6:00 am-10:05 am

1 stop4h 05m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 4/3

5:40 am-11:34 am

1 stop5h 54m

Pensacola

Fri 4/10

2:45 pm-9:00 pm

1 stop6h 15m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 3/8

5:59 pm-11:13 pm

1 stop5h 14m

Pensacola

Fri 3/13

7:34 pm-11:59 pm

1 stop4h 25m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 4/17

7:10 am-2:23 pm

1 stop7h 13m

Pensacola

Fri 4/24

1:59 pm-7:01 pm

1 stop5h 02m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 1/12

6:45 am-1:53 pm

1 stop7h 08m

Pensacola

Mon 1/19

7:00 am-11:59 am

1 stop4h 59m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

12:46 pm-6:42 pm

1 stop5h 56m

Pensacola

Tue 2/24

6:00 am-11:59 am

1 stop5h 59m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/30

6:00 am-10:26 am

1 stop4h 26m

Pensacola

Mon 2/2

1:40 pm-5:29 pm

1 stop3h 49m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

12:46 pm-6:42 pm

1 stop5h 56m

Pensacola

Mon 2/23

1:37 pm-5:45 pm

1 stop4h 08m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 39 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 December 19, 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, July is the cheapest month in which you can book a flight from Chicago to Pensacola Beach (average of $81). Flying from Chicago to Pensacola Beach in December is currently the most expensive (average of $208). 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 December 21, 2025.

It’s optimal to fly from Chicago to Pensacola Beach in the evening. By choosing this option you can save up to 16% on the cost of your flight, compared to a flight in the afternoon.

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 Sunday mornings when fares are most often at their lowest. Monday at noon 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 December 21, 2025.

The most flights from CHI to PB9 are scheduled on a Monday (3 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

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 December 21, 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
4,254 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
9,102 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
11,051 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
8,192 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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.

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

    Airlines like Delta and Southwest fly from Chicago to Pensacola Beach in about 3h 50m. The time it takes to get you to your destination can typically vary by up to 1h 06m. There are 782 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?

    $62 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 $88 and $98, respectively.

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

    Consider United Airlines (83%), Air New Zealand (76%) or Envoy Air (71%) 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 $311 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $153 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $156.

  • 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, July is the cheapest month in which you can book a flight from Chicago to Pensacola Beach (average of $81). Flying from Chicago to Pensacola Beach in December is currently the most expensive (average of $208). 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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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 2,558,603 searches. Data last updated December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$151FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$346FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$372FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$214Average$421FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$218Average$392FlexibilityNo cancel feeOn-time71%

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