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$53+ Cheap flights from Pensacola (PNS) to Chicago (CHI)

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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from Pensacola to Chicago are usually found in April or March, booked 83 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

Cheap flight deals from Pensacola to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

April

Round-trip from

$228
(Delta)

One-way from

$53
(Cheapflightsfares)
Provider with most accurate pricing for Pensacola-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Chicago (CHI) flights.
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High demand for flights, 12% potential price rise
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Best time to find cheap flights, 17% potential price drop
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From Pensacola to Chicago (CHI)
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One-way flight from Pensacola to Chicago (CHI)
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Find flight deals from Pensacola to Chicago

Cheapest flights from Pensacola to Chicago
Explore the most affordable flight options available from Pensacola to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/115:47 pmPNS - ORD
1 stop6h 11mDelta
Sat 12/145:40 amORD - PNS
1 stop4h 26mDelta
Deal found 11/19$228
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/57:00 pmPNS - ORD
2 stops15h 32mSpirit Airlines
Tue 12/105:00 amORD - PNS
1 stop11h 09mSpirit Airlines
Deal found 11/19$229
This CheapOair deal was found by Cheapflights users on 11/18. 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.
Mon 11/255:38 pmPNS - ORD
1 stop18h 37mFrontier
Thu 11/286:00 amORD - PNS
1 stop13h 58mFrontier
Deal found 11/18$232
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/146:00 amPNS - MDW
1 stop3h 50mDelta
Fri 1/36:00 amMDW - PNS
1 stop5h 02mDelta
Deal found 11/19$238
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/27:10 pmPNS - ORD
1 stop25h 05mMultiple Airlines
Fri 12/67:25 amORD - PNS
1 stop10h 57mMultiple Airlines
Deal found 11/19$249
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/127:00 amPNS - ORD
1 stop5h 31mUnited Airlines
Mon 12/1610:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Deal found 11/20$265
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/178:45 amPNS - MDW
1 stop8h 50mSouthwest
Tue 12/241:30 pmMDW - PNS
1 stop5h 20mSouthwest
Deal found 11/19$318
This Southwest deal was found by Cheapflights users on 11/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/184:25 pmPNS - ORD
1 stop5h 35mSouthwest
Fri 12/207:30 amORD - PNS
2 stops10h 20mSouthwest
Deal found 11/18$353
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/207:00 pmPNS - RFD
1 stop14h 24mMultiple Airlines
Fri 1/310:14 amRFD - PNS
1 stop7h 51mMultiple Airlines
Deal found 11/18$376
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/202:39 pmPNS - ORD
1 stop4h 45mAmerican Airlines
Sat 11/305:00 amORD - PNS
1 stop5h 42mAmerican Airlines
Deal found 11/20$413
This Trip.com deal was found by Cheapflights users on 11/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/238:58 pmPNS - MDW
1 stop15h 38mFrontier
Wed 11/279:48 pmMDW - PNS
1 stop22h 10mFrontier
Deal found 11/19$479
This Mytrip deal was found by Cheapflights users on 11/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/187:00 pmPNS - MDW
2 stops22h 51mMultiple Airlines
Fri 12/205:35 pmMDW - PNS
3 stops24h 30mMultiple Airlines
Deal found 11/18$793

Find flights from Pensacola to Chicago within your budget

Customize your flight search to find flights from Pensacola to Chicago 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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 1/3

5:42 pm-10:06 pm

1 stop4h 24m

Chicago Midway

Mon 1/6

10:57 am-5:00 pm

1 stop6h 03m

$228

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 2/13

1:55 pm-10:36 pm

1 stop8h 41m

Chicago O'Hare Intl

Mon 2/17

5:45 am-11:27 am

1 stop5h 42m

$228

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 12/5

7:00 pm-10:32 am

2 stops15h 32m

Chicago O'Hare Intl

Tue 12/10

5:00 am-4:09 pm

1 stop11h 09m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 12/2

7:10 pm-8:15 pm

1 stop25h 05m

Chicago O'Hare Intl

Fri 12/6

7:25 am-6:22 pm

1 stop10h 57m

$249

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 12/12

7:00 am-12:31 pm

1 stop5h 31m

Chicago O'Hare Intl

Mon 12/16

10:55 am-1:31 pm

Nonstop2h 36m

$265

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 12/5

7:17 pm-12:13 am

1 stop28h 56m

Chicago Midway

Mon 12/9

7:15 am-6:13 pm

1 stop10h 58m

$268

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 1/1

5:30 am-11:03 am

1 stop5h 33m

Chicago O'Hare Intl

Fri 1/31

1:54 pm-9:20 pm

1 stop7h 26m

$283

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 2/11

4:10 pm-10:25 pm

1 stop6h 15m

Chicago Midway

Sun 2/16

5:30 am-9:25 am

1 stop3h 55m

$288

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 2/27

7:35 am-6:10 pm

2 stops10h 35m

Chicago O'Hare Intl

Mon 3/3

2:55 pm-9:30 pm

1 stop6h 35m

$323

PensacolaChicago

PNS - RFD

PNSRFD

Pensacola

Fri 12/20

7:00 pm-9:24 am

1 stop14h 24m

Chicago Greater Rockford

Fri 1/3

10:14 am-6:05 pm

1 stop7h 51m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 23 results
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Compare providers for flights from Pensacola to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pensacola to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pensacola-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pensacola-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pensacola-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pensacola-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pensacola-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pensacola to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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.

Travel insights for flights from Pensacola to Chicago

Get recent, data-driven insights about flights from Pensacola to Chicago including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Pensacola to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Pensacola to Chicago. Price data was last updated on November 15, 2024.

The price you pay for your flight from Pensacola to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $232). Flying from Pensacola to Chicago in June is currently the most expensive (average of $308). 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 CHI?

Find hourly flight availability from Pensacola to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 18% on flights from Pensacola to Chicago by exploring options for tickets in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Pensacola to Chicago. Price data was last updated on November 18, 2024.

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 20, 2024.
Get a feel of what it's like to fly with Frontier, Spirit Airlines and United Airlines from Pensacola to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Spirit Airlines
6.3
Okay
8,174 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Related info for your journey

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

    Located just 4.0 mi from the city center, Pensacola is the airport most travelers will use when flying to Chicago from Pensacola. Booking flights from Pensacola (PNS) to Chicago should be relatively easy as there are 3 daily outbound flights to Chicago from 5 different airlines.

  • What are the cheapest airlines flying from Pensacola to Chicago round-trip?

    Our cheapest airline available from Pensacola to Chicago is Delta. Our recent data shows that you can find tickets from as low as $228 on this airline. Additional options worth looking into are Spirit Airlines and Frontier, starting at $229 and $232 round-trip. Delta is 30% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Pensacola to Chicago are Frontier ($53), Spirit Airlines ($81), and United Airlines ($105).

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

    Most travelers choose Pensacola - Chicago O'Hare Intl, Pensacola - Chicago Midway or Pensacola - Chicago Greater Rockford when deciding on the best route from Pensacola to Chicago.

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

    The top 3 most reliable airlines when flying from Pensacola to Chicago are SkyWest Airlines (95%), Lufthansa (93%) and Air New Zealand (93%).

  • What are the cheapest flights from Pensacola to Chicago?

    On average you can expect to pay $382 for a flight from Pensacola to Chicago. The cheapest flight overall is $167 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $167.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $232). Flying from Pensacola to Chicago in June is currently the most expensive (average of $308). 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.

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Alternative routes for Pensacola to Chicago

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Top 5 airlines flying from Pensacola to Chicago

Discover the top 5 airlines that operate flights from Pensacola to Chicago. 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$114Average$185FlexibilityNo cancel feeOn-time65%
DeltaCheapest$197Average$320FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$206Average$307FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$395FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$263Average$465FlexibilityNo cancel feeOn-time63%
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