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Pensacola Beach

$62+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 70 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 February 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/188:30 am
ORD
-
PNS
1 stop9h 12m
Multiple Airlines
Wed 3/46:37 pm
PNS
-
ORD
1 stop23h 09m
Multiple Airlines
Deal found 2/10$218
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/188:30 am
ORD
-
PNS
1 stop9h 12m
Multiple Airlines
Tue 3/36:37 pm
PNS
-
ORD
1 stop21h 15m
Multiple Airlines
Deal found 2/10$219
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/13:40 pm
ORD
-
PNS
1 stop24h 14m
Multiple Airlines
Sun 3/86:37 pm
PNS
-
ORD
1 stop29h 01m
Multiple Airlines
Deal found 2/9$220
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:51 pm
MDW
-
PNS
1 stop19h 51m
Multiple Airlines
Mon 3/167:00 am
PNS
-
MDW
1 stop7h 21m
Multiple Airlines
Deal found 2/9$221
This Mytrip deal was found by Cheapflights users on 2/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/710:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Mon 3/96:37 pm
PNS
-
ORD
2 stops16h 45m
Spirit Airlines
Deal found 2/11$221
This Southwest deal was found by Cheapflights users on 2/9. 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 4/258:10 am
MDW
-
PNS
Nonstop2h 15m
Southwest
Tue 4/287:40 am
PNS
-
MDW
2 stops8h 05m
Southwest
Deal found 2/9$222
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Wed 2/255:20 pm
PNS
-
ORD
1 stop6h 27m
Spirit Airlines
Deal found 2/10$222
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sat 2/288:00 am
MDW
-
PNS
1 stop9h 42m
Multiple Airlines
Sat 3/75:20 pm
PNS
-
MDW
2 stops27h 59m
Multiple Airlines
Deal found 2/7$223
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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 2/2012:44 pm
ORD
-
PNS
1 stop4h 58m
Spirit Airlines
Tue 2/245:20 pm
PNS
-
ORD
1 stop6h 27m
Spirit Airlines
Deal found 2/8$223
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:51 pm
MDW
-
PNS
1 stop23h 23m
Multiple Airlines
Thu 3/199:40 am
PNS
-
MDW
1 stop8h 04m
Multiple Airlines
Deal found 2/10$224
This Travelocity deal was found by Cheapflights users on 2/9. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1610:44 am
ORD
-
PNS
1 stop6h 58m
Multiple Airlines
Mon 3/22:23 pm
PNS
-
ORD
1 stop25h 29m
Multiple Airlines
Deal found 2/9$224
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:14 am
MDW
-
PNS
1 stop12h 07m
Multiple Airlines
Sun 5/177:38 pm
PNS
-
MDW
1 stop12h 26m
Multiple Airlines
Deal found 2/9$225

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$218
(Mytrip)

One-way from

$62
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$301
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. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 11, 2026.
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 5/8

5:59 pm-11:30 pm

1 stop5h 31m

Pensacola

Sun 5/10

6:00 am-10:06 am

1 stop4h 06m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 5/29

2:59 pm-9:53 pm

1 stop6h 54m

Pensacola

Sat 6/6

4:55 pm-9:49 pm

1 stop4h 54m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 4/2

2:32 pm-6:43 pm

1 stop4h 11m

Pensacola

Mon 4/13

7:30 pm-11:59 pm

1 stop4h 29m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 3/7

6:02 pm-8:28 pm

Nonstop2h 26m

Pensacola

Sat 3/14

9:10 am-11:48 am

Nonstop2h 38m

$231

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 5/28

7:30 am-1:25 pm

1 stop5h 55m

Pensacola

Sun 5/31

4:50 pm-7:05 pm

Nonstop2h 15m

$237

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 8/6

1:15 pm-6:02 pm

1 stop4h 47m

Pensacola

Mon 8/10

3:35 pm-8:17 pm

1 stop4h 42m

$237

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 5/28

11:18 am-6:23 pm

1 stop7h 05m

Pensacola

Mon 6/1

7:30 pm-11:59 pm

1 stop4h 29m

$237

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 7/24

1:15 pm-6:02 pm

1 stop4h 47m

Pensacola

Thu 7/30

1:59 pm-8:18 pm

1 stop6h 19m

$237

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 3/30

5:59 pm-11:13 pm

1 stop5h 14m

Pensacola

Wed 4/1

6:00 am-9:59 am

1 stop3h 59m

$237

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 7/7

12:10 pm-4:32 pm

1 stop4h 22m

Pensacola

Sat 7/11

8:00 am-12:09 pm

1 stop4h 09m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 42 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 February 6, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Pensacola Beach, you should look to book at least 70 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 $217). 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 February 11, 2026.

It’s optimal to fly from Chicago to Pensacola Beach in the evening. By choosing this option you can save up to 3% on the cost of your flight, compared to a flight at noon.

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 February 11, 2026.
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
4,280 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,180 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
9,279 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
11,271 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,444 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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, United Airlines, and Southwest fly from Chicago to Pensacola Beach in about 2h 26m. The time it takes to get you to your destination can typically vary by up to 3h 29m. 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?

    $73 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 (81%), Air New Zealand (80%) or Envoy Air (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 $474 for a flight from Chicago to Pensacola Beach. The cheapest flight overall is $158 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $157.

  • 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 $217). 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$170FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$116Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$176Average$343FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$398FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$386FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$212Average$364FlexibilityNo cancel feeOn-time63%

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