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Pensacola Beach

$61+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pensacola Beach are usually found in September or January, 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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$61
(Frontier)

Popular in

March

Cheapest in

September

Average price

$299
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 ($9 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 November 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 November 4, 2025.

This American Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/210:11 amORD - PNS
Nonstop2h 30mAmerican Airlines
Sat 12/61:00 pmPNS - ORD
Nonstop2h 44mAmerican Airlines
Deal found 11/3$209
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/116:15 amORD - PNS
1 stop11h 59mMultiple Airlines
Mon 12/157:09 pmPNS - ORD
1 stop15h 59mMultiple Airlines
Deal found 11/3$212
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Thu 11/206:48 amORD - PNS
1 stop6h 01mSpirit Airlines
Wed 11/265:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 11/3$213
This CheapOair deal was found by Cheapflights users on 11/1. 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.
Wed 11/1910:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Wed 11/265:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 11/1$214
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Sun 11/165:25 amORD - PNS
1 stop28h 57mMultiple Airlines
Thu 11/201:44 pmPNS - ORD
1 stop9h 22mMultiple Airlines
Deal found 11/3$219
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Sun 11/165:25 amORD - PNS
1 stop28h 57mMultiple Airlines
Sat 11/228:16 pmPNS - ORD
1 stop23h 05mMultiple Airlines
Deal found 11/3$220
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Tue 11/2511:48 amORD - PNS
1 stop7h 23mMultiple Airlines
Wed 11/268:16 pmPNS - ORD
1 stop20h 09mMultiple Airlines
Deal found 11/1$221
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Tue 12/210:12 amORD - PNS
1 stop8h 59mSpirit Airlines
Sat 12/67:09 pmPNS - ORD
1 stop15h 59mSpirit Airlines
Deal found 11/3$222
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 11/2510:12 amORD - PNS
1 stop8h 59mSpirit Airlines
Mon 12/15:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 11/3$223
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/15:00 amORD - PNS
1 stop14h 11mMultiple Airlines
Sat 12/64:44 pmPNS - ORD
1 stop18h 44mMultiple Airlines
Deal found 11/3$224
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/105:00 amORD - PNS
1 stop8h 13mSpirit Airlines
Fri 12/127:09 pmPNS - ORD
1 stop15h 59mSpirit Airlines
Deal found 11/3$225
This Delta deal was found by Cheapflights users on 11/3. 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 12/15:34 pmMDW - PNS
1 stop4h 26mDelta
Sun 12/76:00 amPNS - MDW
1 stop5h 55mDelta
Deal found 11/3$229

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 November 4, 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

Thu 12/4

10:50 am-1:17 pm

Nonstop2h 27m

Pensacola

Mon 12/8

2:15 pm-4:47 pm

Nonstop2h 32m

$209

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 12/10

10:50 am-1:17 pm

Nonstop2h 27m

Pensacola

Sat 12/13

2:39 pm-5:10 pm

Nonstop2h 31m

$209

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 12/11

6:00 am-10:41 am

1 stop4h 41m

Pensacola

Mon 12/15

5:45 pm-11:47 pm

1 stop6h 02m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

6:00 am-12:32 pm

1 stop6h 32m

Pensacola

Tue 2/24

6:00 am-12:01 pm

1 stop6h 01m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 12/12

12:50 pm-4:34 pm

1 stop3h 44m

Pensacola

Mon 12/15

7:15 am-11:55 am

1 stop4h 40m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 11/20

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Wed 11/26

2:17 pm-4:48 pm

Nonstop2h 31m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 12/9

12:50 pm-4:34 pm

1 stop3h 44m

Pensacola

Thu 12/11

7:15 am-11:55 am

1 stop4h 40m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 12/13

6:00 am-12:41 pm

1 stop6h 41m

Pensacola

Mon 12/15

11:46 am-4:34 pm

1 stop4h 48m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

12:46 pm-6:44 pm

1 stop5h 58m

Pensacola

Mon 2/23

5:42 pm-10:44 pm

1 stop5h 02m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 12/9

6:00 am-10:37 am

1 stop4h 37m

Pensacola

Mon 12/15

6:00 am-11:55 am

1 stop5h 55m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 44 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 October 31, 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, 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 August is currently the most expensive (average of $200). 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 November 4, 2025.

It’s optimal to fly from Chicago to Pensacola Beach in the evening. By choosing this option you can save up to 23% 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 November 4, 2025.

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

How much does it cost to fly round-trip from Chicago to Pensacola Beach?

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 November 4, 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
4,238 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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.
Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

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.

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

    Airlines like United Airlines and Delta fly from Chicago to Pensacola Beach in about 2h 27m. The time it takes to get you to your destination can typically vary by up to 2h 14m. 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?

    $92 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 United Airlines, with prices starting from $98 and $105, respectively.

  • What are the cheapest flights from Chicago to Pensacola Beach?

    On average you can expect to pay $271 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 $183.

  • 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 August is currently the most expensive (average of $200). 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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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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$168FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$392FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$385FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$400FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$410FlexibilityNo cancel feeOn-time69%

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