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Pensacola

$70+ Cheap flights from Illinois to Pensacola (PNS)

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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
1 adult, Economy
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Cheap flight deals from Illinois to Pensacola

Cheapest flights from Illinois to Pensacola
Explore the most affordable flight options available from Illinois to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 7, 2025.

This Mytrip deal was found by Cheapflights users on 12/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:00 amORD - PNS
1 stop11h 21mFrontier
Wed 12/247:26 pmPNS - ORD
1 stop28h 46mFrontier
Deal found 12/7$227
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/215:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Sun 12/281:12 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 12/6$239
This United Airlines deal was found by Cheapflights users on 12/6. 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 12/2410:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Fri 12/262:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Deal found 12/6$249
This United Airlines deal was found by Cheapflights users on 12/5. 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 12/2310:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Fri 12/262:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Deal found 12/5$253
This United Airlines deal was found by Cheapflights users on 12/6. 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.
Thu 12/2510:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Tue 12/302:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Deal found 12/6$258
This American Airlines deal was found by Cheapflights users on 12/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:21 amORD - PNS
1 stop5h 18mAmerican Airlines
Wed 12/2412:58 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 12/7$259
This American Airlines deal was found by Cheapflights users on 12/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amORD - PNS
1 stop8h 49mAmerican Airlines
Mon 1/56:10 amPNS - ORD
1 stop7h 04mAmerican Airlines
Deal found 12/7$269
This United Airlines deal was found by Cheapflights users on 12/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:50 amORD - PNS
Nonstop2h 26mUnited Airlines
Sun 12/212:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Deal found 12/7$284
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Wed 12/313:26 pmORD - PNS
1 stop26h 48mMultiple Airlines
Mon 1/57:54 pmPNS - ORD
2 stops24h 10mMultiple Airlines
Deal found 12/7$287
This Super.com deal was found by Cheapflights users on 12/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:10 amORD - PNS
1 stop11h 04mSpirit Airlines
Tue 12/162:08 pmPNS - ORD
1 stop10h 01mSpirit Airlines
Deal found 12/7$288
This American Airlines deal was found by Cheapflights users on 12/6. 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 12/1810:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Thu 1/15:19 amPNS - ORD
1 stop7h 21mAmerican Airlines
Deal found 12/6$294
This American Airlines deal was found by Cheapflights users on 12/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:00 amPIA - PNS
1 stop5h 15mAmerican Airlines
Mon 12/291:12 pmPNS - PIA
1 stop6h 17mAmerican Airlines
Deal found 12/7$294

Find flight deals from Illinois to Pensacola

Keep the following information in mind while searching for Illinois to Pensacola flight deals. Data was last updated December 7, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$192
(Kiwi.com)

One-way from

$70
(Southwest)

Popular in

March

Cheapest in

September

Average price

$348

Good round-trip deal

$277 or less

Good one-way deal

$238 or less
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 Illinois to Pensacola
Search Deals
One-way flight from Illinois to Pensacola
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Pensacola.
Search Deals
Price to beat on a one-way flight from Illinois to Pensacola.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Pensacola 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 7, 2025.
Use the filters below to find and compare flights from Illinois to Pensacola that are best for you.

Fly from

Illinois

Fly to

Pensacola

Route

Depart

Return

Price

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 1/21

12:48 pm-6:42 pm

1 stop5h 54m

Pensacola

Wed 1/28

1:40 pm-5:29 pm

1 stop3h 49m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 2/17

5:55 am-11:20 am

1 stop5h 25m

Pensacola

Sat 2/21

10:15 am-5:55 pm

1 stop7h 40m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 1/18

10:45 am-1:32 pm

Nonstop2h 47m

Pensacola

Fri 1/23

2:13 pm-4:59 pm

Nonstop2h 46m

$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

Wed 2/18

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Mon 2/23

1:37 pm-5:45 pm

1 stop4h 08m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/9

5:31 pm-11:13 pm

1 stop5h 42m

Pensacola

Sun 1/11

6:00 am-10:27 am

1 stop4h 27m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 1/20

6:00 am-12:35 pm

1 stop6h 35m

Pensacola

Fri 1/23

1:40 pm-5:29 pm

1 stop3h 49m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 1/28

12:48 pm-6:42 pm

1 stop5h 54m

Pensacola

Fri 1/30

6:00 am-11:59 am

1 stop5h 59m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/11

6:00 am-12:35 pm

1 stop6h 35m

Pensacola

Wed 2/18

6:00 am-9:56 am

1 stop3h 56m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 2/6

5:30 am-12:35 pm

1 stop7h 05m

Pensacola

Sun 2/8

1:50 pm-7:35 pm

1 stop5h 45m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from Illinois 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 Illinois to Pensacola

What is the cheapest month to book a flight from Illinois to Pensacola?

Currently, July is the cheapest month in which you can book a flight from Illinois to Pensacola (average of $81). Flying from Illinois to Pensacola in February is currently the most expensive (average of $130). 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 IL to PNS?

Find hourly flight availability from Illinois to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 7, 2025.

It’s optimal to fly from Illinois to Pensacola in the evening. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Illinois to Pensacola?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Pensacola. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to Pensacola flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Illinois to Pensacola

Explore weekly flight availability from Illinois to Pensacola. 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 7, 2025.

The most flights from USIL to PNS 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).

Related info for your journey

Find useful and relevant information for your journey from Illinois to Pensacola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Pensacola from Illinois?

    Most people fly into Pensacola (PNS) if they book a flight to Pensacola from Illinois. Pensacola is conveniently located just 4.0 mi from Pensacola’s city center.

  • How long is the flight from Illinois to Pensacola?

    Airlines like Delta, United Airlines, and American Airlines fly from Illinois to Pensacola in about 2h 47m. The time it takes to get you to your destination can typically vary by up to 3h 15m. There are 795 mi between Illinois and Pensacola. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $62. Delta flights start at $88 while deals on Southwest start at $98 one-way.

  • What are the most popular routes from Illinois to Pensacola?

    Most travelers choose Chicago O'Hare Intl - Pensacola, Chicago Midway - Pensacola or Lambert-St Louis - Pensacola when deciding on the best route from Illinois to Pensacola.

  • What are the most reliable airlines from Illinois to Pensacola?

    The top 3 most reliable airlines when flying from Illinois to Pensacola are United Airlines (82%), Air New Zealand (78%) and American Airlines (70%).

  • What are the cheapest flights from Illinois to Pensacola?

    Looking for the cheapest flight from Illinois to Pensacola? While on average our users pay $309, our data indicates the cheapest price to be $209. The most popular route (Chicago O'Hare Intl - Pensacola), is priced around $155.

  • Can I find deals for flights from Illinois to Pensacola that include hotel bookings?

    Yes. In addition to deals on Illinois to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Pensacola.

  • Can I find deals for business class flights from Illinois to Pensacola?

    Yes. Cheapflights offers flight deals from Illinois to Pensacola 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 Illinois to Pensacola?

    Currently, July is the cheapest month in which you can book a flight from Illinois to Pensacola (average of $81). Flying from Illinois to Pensacola in February is currently the most expensive (average of $130). 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

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Gulf Breeze
Navarre
Foley
Perdido Key
Navarre Beach
Warrington

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Alternative routes for Illinois to Pensacola

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Top 5 airlines flying from Illinois to Pensacola

Discover the top 5 airlines that operate flights from Illinois to Pensacola. 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 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$352FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$365FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$216Average$368FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$218Average$415FlexibilityNo cancel feeOn-time71%

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