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$60+ Cheap flights from Pensacola (PNS) to Illinois

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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap flight deals from Pensacola to Illinois

Cheapest flights from Pensacola to Illinois
Explore the most affordable flight options available from Pensacola to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This United Airlines deal was found by Cheapflights users on 12/4. 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 12/222:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Wed 1/710:45 amORD - PNS
Nonstop2h 47mUnited Airlines
Deal found 12/4$212
This United Airlines deal was found by Cheapflights users on 12/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Wed 1/710:45 amORD - PNS
Nonstop2h 47mUnited Airlines
Deal found 12/3$217
This Trip.com deal was found by Cheapflights users on 12/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Fri 1/27:30 amORD - PNS
1 stop10h 44mSpirit Airlines
Deal found 12/3$219
This Delta deal was found by Cheapflights users on 12/4. 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.
Thu 12/186:00 amPNS - ORD
1 stop6h 10mDelta
Sat 1/245:30 amORD - PNS
1 stop4h 56mDelta
Deal found 12/4$223
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/311:58 pmPNS - ORD
2 stops32h 26mMultiple Airlines
Wed 1/75:29 pmORD - PNS
1 stop23h 08mMultiple Airlines
Deal found 12/3$225
This United Airlines deal was found by Cheapflights users on 12/4. 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 12/242:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Sat 1/310:45 amORD - PNS
Nonstop2h 36mUnited Airlines
Deal found 12/4$229
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/227:54 pmPNS - ORD
2 stops46h 45mMultiple Airlines
Wed 1/75:29 pmORD - PNS
1 stop23h 08mMultiple Airlines
Deal found 12/4$231
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/172:08 pmPNS - ORD
1 stop24h 54mMultiple Airlines
Sat 1/2412:44 pmORD - PNS
1 stop27h 53mMultiple Airlines
Deal found 12/4$232
This Super.com deal was found by Cheapflights users on 12/4. 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.
Wed 12/241:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Sat 1/37:30 amORD - PNS
1 stop10h 44mSpirit Airlines
Deal found 12/4$233
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Thu 12/2512:58 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Wed 12/315:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Deal found 12/3$239
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/157:09 pmPNS - ORD
2 stops23h 37mMultiple Airlines
Sat 1/2412:44 pmORD - PNS
1 stop27h 53mMultiple Airlines
Deal found 12/4$246
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/313:20 pmPNS - MLI
1 stop5h 32mAmerican Airlines
Wed 1/73:58 pmMLI - PNS
1 stop5h 14mAmerican Airlines
Deal found 12/2$249

Find flight deals from Pensacola to Illinois

Keep the following information in mind while searching for Pensacola to Illinois flight deals. Data was last updated December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$119
(United Airlines)

One-way from

$60
(United Airlines)

Popular in

March

Cheapest in

February

Average price

$347

Good round-trip deal

$294 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Pensacola-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pensacola-Chicago (CHI) flights.
Search Deals
From Pensacola to Illinois
Search Deals
One-way flight from Pensacola to Illinois
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 Pensacola to Illinois.
Search Deals
Price to beat on a one-way flight from Pensacola to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pensacola to Illinois 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 4, 2025.
Use the filters below to find and compare flights from Pensacola to Illinois that are best for you.

Fly from

Pensacola

Fly to

Illinois

Route

Depart

Return

Price

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 1/27

7:50 am-1:20 pm

1 stop5h 30m

Chicago Midway

Sat 1/31

6:40 am-5:05 pm

2 stops10h 25m

$177

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 2/14

6:00 am-10:07 am

1 stop4h 07m

Chicago O'Hare Intl

Wed 2/18

2:46 pm-6:42 pm

1 stop3h 56m

$177

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 1/15

2:58 pm-7:35 pm

1 stop4h 37m

Chicago O'Hare Intl

Sat 1/17

8:00 am-1:49 pm

1 stop5h 49m

$177

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 1/8

5:54 pm-10:07 pm

1 stop4h 13m

Chicago Midway

Fri 1/9

5:31 pm-11:13 pm

1 stop5h 42m

$194

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 1/16

5:54 pm-10:07 pm

1 stop4h 13m

Chicago Midway

Mon 1/19

6:00 am-10:26 am

1 stop4h 26m

$194

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 1/16

10:06 am-4:29 pm

1 stop6h 23m

Chicago Midway

Wed 1/28

12:48 pm-6:42 pm

1 stop5h 54m

$194

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 2/20

7:26 pm-11:57 pm

1 stop4h 31m

Chicago O'Hare Intl

Mon 2/23

9:48 am-2:54 pm

1 stop5h 06m

$194

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 3/6

7:00 am-9:39 am

Nonstop2h 39m

Chicago O'Hare Intl

Sun 3/8

10:50 am-1:16 pm

Nonstop2h 26m

$209

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 12/22

2:33 pm-5:07 pm

Nonstop2h 34m

Chicago O'Hare Intl

Wed 1/7

10:45 am-1:32 pm

Nonstop2h 47m

$212

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 1/29

4:00 pm-10:05 pm

1 stop6h 05m

Chicago Midway

Sun 2/1

5:55 am-11:20 am

1 stop5h 25m

$222

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 Pensacola to Illinois

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

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

Currently, June is the cheapest month in which you can book a flight from Pensacola to Illinois (average of $78). Flying from Pensacola to Illinois in December is currently the most expensive (average of $233). 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 PNS to IL?

Find hourly flight availability from Pensacola to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 4, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 25% on flights from Pensacola to Illinois by exploring options for tickets in the evening.

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

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated December 4, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Pensacola to Illinois to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
9,066 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,047 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,157 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Pensacola to Illinois. 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 from for flights from Pensacola to Illinois?

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

  • How long is the flight from Pensacola to Illinois?

    For as low as $209, Southwest can have you in Illinois from Pensacola in 2h 39m. There are 795 mi between Pensacola and Illinois. Both multi-stop and nonstop flights can be found to your destination and back.

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

    One-way options have recently been found by users for as low as $87 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $98 and American Airlines from $104 one-way.

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

    When deciding which route to take from Pensacola to Illinois consider Pensacola - Chicago O'Hare Intl, Pensacola - Chicago Midway or Pensacola - Moline Quad-City as they are the most popular.

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

    The top 3 most reliable airlines when flying from Pensacola to Illinois are Lufthansa (96%), Emirates (81%) and American Airlines (79%).

  • What are the cheapest flights from Pensacola to Illinois?

    On average you can expect to pay $327 for a flight from Pensacola to Illinois. The cheapest flight overall is $122 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $160.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Pensacola to Illinois (average of $78). Flying from Pensacola to Illinois in December is currently the most expensive (average of $233). 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 Pensacola to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Pensacola to Illinois

Discover the top 5 airlines that operate flights from Pensacola to Illinois. 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$317FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$296FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$315FlexibilityNo cancel feeOn-time71%

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