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Pensacola

$80+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/173:49 pm
STL
-
PNS
1 stop25h 53m
Multiple Airlines
Tue 2/246:37 pm
PNS
-
STL
1 stop27h 50m
Multiple Airlines
Deal found 1/18$169
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/163:49 pm
STL
-
PNS
1 stop25h 53m
Multiple Airlines
Mon 2/236:37 pm
PNS
-
STL
1 stop27h 50m
Multiple Airlines
Deal found 1/19$171
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/183:49 pm
STL
-
PNS
1 stop25h 53m
Multiple Airlines
Wed 2/256:37 pm
PNS
-
STL
2 stops36h 14m
Multiple Airlines
Deal found 1/21$207
This CheapOair deal was found by Cheapflights users on 1/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:49 pm
ORD
-
PNS
1 stop5h 32m
Spirit Airlines
Tue 5/121:47 pm
PNS
-
ORD
1 stop6h 01m
Spirit Airlines
Deal found 1/18$209
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Thu 2/125:05 am
ORD
-
PNS
2 stops37h 46m
Multiple Airlines
Tue 2/175:20 pm
PNS
-
ORD
1 stop18h 02m
Multiple Airlines
Deal found 1/20$210
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/87:20 am
ORD
-
PNS
1 stop7h 48m
Spirit Airlines
Mon 2/94:03 pm
PNS
-
ORD
1 stop19h 19m
Spirit Airlines
Deal found 1/18$211
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/87:20 am
ORD
-
PNS
1 stop7h 48m
Multiple Airlines
Fri 2/135:20 pm
PNS
-
ORD
1 stop26h 30m
Multiple Airlines
Deal found 1/18$212
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/610:48 am
ORD
-
PNS
1 stop5h 49m
Spirit Airlines
Sun 2/84:03 pm
PNS
-
ORD
1 stop7h 44m
Spirit Airlines
Deal found 1/20$213
This Priceline deal was found by Cheapflights users on 1/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/310:48 am
ORD
-
PNS
1 stop5h 49m
Spirit Airlines
Fri 2/64:03 pm
PNS
-
ORD
1 stop7h 44m
Spirit Airlines
Deal found 1/20$214
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:58 pm
ORD
-
PNS
2 stops23h 44m
Spirit Airlines
Fri 2/275:20 pm
PNS
-
ORD
1 stop6h 27m
Spirit Airlines
Deal found 1/20$217
This Southwest deal was found by Cheapflights users on 1/21. 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.
Thu 3/511:40 am
MDW
-
PNS
1 stop5h 05m
Southwest
Mon 3/95:25 pm
PNS
-
MDW
Nonstop2h 15m
Southwest
Deal found 1/21$217
This Cheapflightsfares deal was found by Cheapflights users on 1/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/2610:48 am
ORD
-
PNS
1 stop5h 49m
Spirit Airlines
Mon 2/24:03 pm
PNS
-
ORD
1 stop7h 44m
Spirit Airlines
Deal found 1/18$218

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 January 21, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$169
(Kiwi.com)

One-way from

$80
(Priceline)

Popular in

March

Cheapest in

September

Average price

$353

Good round-trip deal

$294 or less

Good one-way deal

$190 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. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 21, 2026.
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

Thu 3/5

11:40 am-4:45 pm

1 stop5h 05m

Pensacola

Mon 3/9

5:25 pm-7:40 pm

Nonstop2h 15m

$217

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 3/4

9:52 am-2:54 pm

1 stop5h 02m

Pensacola

Wed 3/11

12:16 pm-6:53 pm

1 stop6h 37m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 2/24

6:00 am-10:31 am

1 stop4h 31m

Pensacola

Fri 2/27

4:04 pm-10:31 pm

1 stop6h 27m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 4/11

7:25 am-2:10 pm

1 stop6h 45m

Pensacola

Wed 4/15

7:40 am-1:30 pm

1 stop5h 50m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 4/12

6:00 am-11:11 am

1 stop5h 11m

Pensacola

Thu 4/16

11:04 am-4:36 pm

1 stop5h 32m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 2/9

6:00 am-12:35 pm

1 stop6h 35m

Pensacola

Fri 2/13

5:48 pm-10:31 pm

1 stop4h 43m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 3/12

6:00 am-10:06 am

1 stop4h 06m

Pensacola

Sun 3/15

6:00 am-9:56 am

1 stop3h 56m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 3/5

6:40 pm-11:11 pm

1 stop4h 31m

Pensacola

Sun 3/8

6:00 am-9:56 am

1 stop3h 56m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/7

6:35 am-5:05 pm

1 stop10h 30m

Pensacola

Tue 2/10

4:00 pm-10:05 pm

1 stop6h 05m

$233

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 3/24

12:15 pm-2:25 pm

Nonstop2h 10m

Pensacola

Fri 3/27

3:00 pm-8:45 pm

1 stop5h 45m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 March is currently the most expensive (average of $121). 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 January 21, 2026.

It’s optimal to fly from Illinois to Pensacola at noon. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the afternoon.

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 January 21, 2026.

The most flights from USIL to PNS are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 Southwest, Delta, and United Airlines fly from Illinois to Pensacola in about 2h 27m. The time it takes to get you to your destination can typically vary by up to 2h 38m. 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 $63. 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 (80%), Air New Zealand (80%) and Republic Airways (67%).

  • What are the cheapest flights from Illinois to Pensacola?

    Looking for the cheapest flight from Illinois to Pensacola? While on average our users pay $506, our data indicates the cheapest price to be $159. The most popular route (Chicago O'Hare Intl - Pensacola), is priced around $178.

  • 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 March is currently the most expensive (average of $121). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Illinois to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$213FlexibilityNo cancel feeOn-time65%
DeltaCheapest$154Average$361FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$198Average$398FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$365FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$214Average$356FlexibilityNo cancel feeOn-time63%

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