HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pensacola

$63+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Pensacola with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find 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 October 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/811:36 amMDW - PNS
1 stop22h 46mMultiple Airlines
Wed 11/124:44 pmPNS - MDW
2 stops25h 55mMultiple Airlines
Deal found 10/16$207
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/1110:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Wed 11/128:16 pmPNS - ORD
1 stop14h 56mSpirit Airlines
Deal found 10/15$208
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Fri 11/1410:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Mon 11/172:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 10/15$209
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/1210:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Fri 11/1411:17 amPNS - ORD
1 stop11h 49mSpirit Airlines
Deal found 10/15$210
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/83:26 pmORD - PNS
1 stop27h 45mMultiple Airlines
Wed 11/124:44 pmPNS - ORD
2 stops17h 57mMultiple Airlines
Deal found 10/16$211
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/95:25 amORD - PNS
1 stop28h 57mMultiple Airlines
Fri 11/144:30 pmPNS - ORD
1 stop7h 45mMultiple Airlines
Deal found 10/15$213
This CheapOair deal was found by Cheapflights users on 10/14. 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 10/296:00 amORD - PNS
1 stop11h 01mSpirit Airlines
Sun 11/211:17 amPNS - ORD
1 stop11h 49mSpirit Airlines
Deal found 10/14$214
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/83:26 pmORD - PNS
1 stop27h 45mSpirit Airlines
Wed 11/128:16 pmPNS - ORD
1 stop14h 56mSpirit Airlines
Deal found 10/16$218
This Southwest deal was found by Cheapflights users on 10/15. 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 11/1910:50 amMDW - PNS
1 stop4h 45mSouthwest
Tue 11/2512:05 pmPNS - MDW
1 stop7h 40mSouthwest
Deal found 10/15$218
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/510:30 amORD - PNS
Nonstop2h 30mAmerican Airlines
Tue 11/111:32 pmPNS - ORD
Nonstop2h 39mAmerican Airlines
Deal found 10/15$219
This Mytrip deal was found by Cheapflights users on 10/14. 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.
Thu 11/610:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Wed 11/128:16 pmPNS - ORD
1 stop14h 56mSpirit Airlines
Deal found 10/14$220
This Delta deal was found by Cheapflights users on 10/15. 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 11/196:45 amORD - PNS
1 stop5h 56mDelta
Tue 11/257:10 pmPNS - ORD
1 stop4h 52mDelta
Deal found 10/15$223

Cheap flight deals from Illinois to Pensacola

Keep the following information in mind while searching for Illinois to Pensacola flight deals. Data was last updated October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$205
(CheapOair)

One-way from

$80
(Frontier)

Popular in

March

Cheapest in

September

Average price

$339

Good round-trip deal

$222 or less

Good one-way deal

$136 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 October 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 October 16, 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

Sat 11/8

11:36 am-10:22 am

1 stop22h 46m

Pensacola

Wed 11/12

4:44 pm-6:39 pm

2 stops25h 55m

$207

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 12/18

10:55 am-1:31 pm

Nonstop2h 36m

Pensacola

Thu 12/25

2:33 pm-5:07 pm

Nonstop2h 34m

$209

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 11/14

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Mon 11/17

2:17 pm-4:48 pm

Nonstop2h 31m

$209

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/19

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Sun 11/23

4:30 pm-12:10 am

1 stop7h 40m

$218

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/19

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Tue 11/25

12:05 pm-7:45 pm

1 stop7h 40m

$218

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 11/5

9:52 am-3:05 pm

1 stop5h 13m

Pensacola

Sun 11/9

6:00 am-10:19 am

1 stop4h 19m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 12/12

5:30 am-12:41 pm

1 stop7h 11m

Pensacola

Sun 12/14

5:45 pm-12:02 am

1 stop6h 17m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 1/1

5:30 am-10:20 am

1 stop4h 50m

Pensacola

Thu 1/8

6:00 am-10:06 am

1 stop4h 06m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 12/19

5:25 am-9:10 am

1 stop3h 45m

Pensacola

Mon 12/22

6:10 pm-12:45 am

1 stop6h 35m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 12/14

5:30 am-12:41 pm

1 stop7h 11m

Pensacola

Tue 1/6

7:00 am-1:23 pm

1 stop6h 23m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 60 results
1
2
3
...
6

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, December is the cheapest month in which you can book a flight from Illinois to Pensacola (average of $78). 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 October 16, 2025.

It’s optimal to fly from Illinois to Pensacola in the evening. By choosing this option you can save up to 34% 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 October 16, 2025.

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 United Airlines, Southwest, and Delta fly from Illinois to Pensacola in about 2h 36m. The time it takes to get you to your destination can typically vary by up to 2h 37m. 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 Frontier, which is currently one of the cheapest options available, starting at $63. United Airlines flights start at $99 while deals on Southwest start at $104 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 cheapest flights from Illinois to Pensacola?

    Looking for the cheapest flight from Illinois to Pensacola? While on average our users pay $235, our data indicates the cheapest price to be $104. The most popular route (Chicago O'Hare Intl - Pensacola), is priced around $172.

  • 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, December is the cheapest month in which you can book a flight from Illinois to Pensacola (average of $78). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Miami flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Fort Lauderdale flights
Newark to Orlando flights
Newark to Miami flights
LaGuardia to Miami flights
John F Kennedy Intl to Tampa flights
Dallas/Fort Worth to Orlando flights
John F Kennedy Intl to West Palm Beach flights
O'Hare Intl to Orlando flights
LaGuardia to Tampa flights
Newark to Tampa flights
Boston to Orlando flights
Reagan-National to Miami flights
Philadelphia to Orlando flights
Dulles Intl to Miami flights
Dulles Intl to Orlando flights
Baltimore to Orlando flights
Boston to Miami flights
Los Angeles to Miami flights
Los Angeles to Orlando flights
Newark to West Palm Beach flights
Baltimore to Fort Lauderdale flights
Boston to Tampa flights
Boston to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Lauderdale flights
Detroit to Fort Lauderdale flights
Baltimore to Miami flights
Cleveland to Orlando flights
O'Hare Intl to Miami flights
Philadelphia to Fort Lauderdale flights
Los Angeles to Fort Lauderdale flights
LaGuardia to West Palm Beach flights
Detroit to Orlando flights
Reagan-National to Orlando flights
Seattle to Orlando flights
Minneapolis to Orlando flights
Cincinnati to Orlando flights
Denver to Orlando flights
Atlanta to Miami flights
Providence to Orlando flights
Newark to Fort Myers flights
Detroit to Miami flights
Denver to Miami flights
Philadelphia to Miami flights
Hartford to Orlando flights

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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$351FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$214Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$220Average$368FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.