HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pensacola

$79+ Cheap flights from O'Hare Intl (ORD) 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl 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.

Cheapflights Tip: The best prices from Chicago O'Hare Intl to Pensacola are usually found in January or May, booked 13 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Pensacola (PNS). 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 June 18, 2025.

Round-trip from

$221
(Cheapflightsfares)

One-way from

$79
(FlightHub)

Popular in

August

Cheapest in

January

Average price

$332

Good round-trip deal

$301 or less

Good one-way deal

$138 or less
From Chicago O'Hare Intl to Pensacola
Search Deals
One-way flight from Chicago O'Hare Intl to Pensacola
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 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 June 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Pensacola.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Pensacola.
Search Deals

Find flight deals from O'Hare Intl to Pensacola

Cheapest flights from O'Hare Intl to Pensacola
Explore the most affordable flight options available from O'Hare Intl to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/44:36 pmORD - PNS
1 stop6h 05mSpirit Airlines
Thu 8/76:00 amPNS - ORD
1 stop9h 31mSpirit Airlines
Deal found 6/15$221
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/145:40 amORD - PNS
1 stop9h 54mFrontier
Fri 7/184:29 pmPNS - ORD
1 stop7h 41mFrontier
Deal found 6/17$276
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 7/910:39 amORD - PNS
Nonstop2h 27mUnited Airlines
Mon 7/282:08 pmPNS - ORD
Nonstop2h 39mUnited Airlines
Deal found 6/15$277
This American Airlines deal was found by Cheapflights users on 6/17. 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 7/97:05 amORD - PNS
1 stop5h 13mAmerican Airlines
Sat 7/1211:36 amPNS - ORD
Nonstop2h 39mAmerican Airlines
Deal found 6/17$287
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:00 amORD - PNS
1 stop6h 50mDelta
Sat 10/1811:59 amPNS - ORD
1 stop4h 39mDelta
Deal found 6/18$297
This FlightHub deal was found by Cheapflights users on 6/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1710:46 amORD - PNS
1 stop11h 51mMultiple Airlines
Fri 6/204:29 pmPNS - ORD
1 stop7h 30mMultiple Airlines
Deal found 6/16$310
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:00 amORD - PNS
2 stops13h 00mSouthwest
Mon 9/2911:05 amPNS - ORD
1 stop5h 20mSouthwest
Deal found 6/16$325

Cheapflights Fare Finder

Customize your flight search to find flights from O'Hare Intl 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 June 18, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Pensacola that are best for you.

Fly from

O'Hare Intl

Fly to

Pensacola

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 8/4

4:36 pm-10:41 pm

1 stop6h 05m

Pensacola

Thu 8/7

6:00 am-3:31 pm

1 stop9h 31m

$221

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 7/14

5:40 am-3:34 pm

1 stop9h 54m

Pensacola

Fri 7/18

4:29 pm-12:10 am

1 stop7h 41m

$276

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 7/9

10:39 am-1:06 pm

Nonstop2h 27m

Pensacola

Mon 7/28

2:08 pm-4:47 pm

Nonstop2h 39m

$277

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 7/9

7:05 am-12:18 pm

1 stop5h 13m

Pensacola

Sat 7/12

11:36 am-2:15 pm

Nonstop2h 39m

$287

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 10/14

6:00 am-12:50 pm

1 stop6h 50m

Pensacola

Sat 10/18

11:59 am-4:38 pm

1 stop4h 39m

$297

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 8/21

7:30 am-7:00 pm

2 stops11h 30m

Pensacola

Mon 8/25

11:05 am-4:25 pm

1 stop5h 20m

$325

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 6/29

12:05 pm-7:31 pm

3 stops31h 26m

Pensacola

Fri 7/11

6:00 am-5:58 pm

1 stop11h 58m

$353

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 7/7

7:39 pm-7:51 am

1 stop12h 12m

$79

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 11/4

10:35 am-1:05 pm

Nonstop2h 30m

$139

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 11/10

5:00 am-9:42 am

1 stop4h 42m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 13 results
1
2

Best time to book a flight from O'Hare Intl to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from O'Hare Intl 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 Chicago O'Hare Intl Airport to Pensacola

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Pensacola?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Pensacola. Price data was last updated on June 13, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Pensacola is 13 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Pensacola?

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Pensacola (average of $306). Flying from Chicago O'Hare Intl Airport to Pensacola in March is currently the most expensive (average of $417). 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 ORD to PNS?

Find hourly flight availability from O'Hare Intl 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 June 18, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Pensacola is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 36% on airfare.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Pensacola?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Pensacola. Price data was last updated on June 15, 2025.

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

Weekly flight availability from Chicago O'Hare Intl Airport to Pensacola

Explore weekly flight availability from O'Hare Intl 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 June 18, 2025.

The most flights from ORD 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).

Rainfall in Pensacola by month

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

In terms of precipitation, rainfall in Pensacola ranges from 4.2 - 7.4 inches per month. July is typically the wettest month, when rainfall can reach 7.4 in. May is typically the driest time to visit Pensacola when rainfall is around 4.2 in.

Temperature in Pensacola by month

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

If weather is an important factor for your trip to Pensacola, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. 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 Pensacola. Reviews last updated June 18, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Chicago to Pensacola. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,810 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,066 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl 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 Chicago O'Hare Intl?

    Most people fly into Pensacola (PNS) if they book a flight to Pensacola from Chicago O'Hare Intl. On average, Pensacola has 2 inbound flights from Chicago O'Hare Intl per day from 5 airlines. Pensacola is conveniently located just 4.0 mi from Pensacola’s city center.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Pensacola round-trip?

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Pensacola round-trip from $221. Other airlines that can offer you cheap pricing are Frontier, from $276, and United Airlines, from $277. Users have found that Spirit Airlines is 38% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Pensacola one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Pensacola are Spirit Airlines ($79), United Airlines ($139), and American Airlines ($149).

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Pensacola?

    Consider United Airlines (93%), Air New Zealand (93%) or Envoy Air (88%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Pensacola.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Pensacola?

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $171 on average our data indicates $325 when flying from Chicago O'Hare Intl Airport to Pensacola.

  • Can I find deals for flights from O'Hare Intl to Pensacola that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Pensacola?

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

  • Can I find deals for business class flights from O'Hare Intl to Pensacola?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 Chicago O'Hare Intl Airport to Pensacola?

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Pensacola (average of $306). Flying from Chicago O'Hare Intl Airport to Pensacola in March is currently the most expensive (average of $417). 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Navarre
Gulf Breeze
Foley
Perdido Key
Milton
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 O'Hare Intl to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
Midway to Orlando flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Lauderdale flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Jacksonville flights
Midway to West Palm Beach flights
Midway to Tampa flights
O'Hare Intl to Key West flights
O'Hare Intl to Panama City flights
Midway to Fort Myers flights
Midway to Jacksonville flights
Midway to Key West flights
Midway to Pensacola flights
Midway to Sarasota flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to St Petersburg flights
Midway to Panama City flights
O'Hare Intl to Valparaiso flights
O'Hare Intl to Gainesville flights
Rockford to St Petersburg flights
O'Hare Intl to Tallahassee flights
O'Hare Intl to Daytona Beach flights
O'Hare Intl to Melbourne flights
O'Hare Intl to Orlando Sanford Intl flights
Midway to Valparaiso flights
O'Hare Intl to Punta Gorda flights
Midway to Punta Gorda flights
Midway to Gainesville flights
Midway to Orlando Sanford Intl flights
Midway to Tallahassee flights
Midway to Melbourne flights
Midway to Daytona Beach flights
Rockford to Punta Gorda flights
Midway to Valdosta flights
O'Hare Intl to Valdosta flights
O'Hare Intl to Destin flights

Top 5 airlines flying from O'Hare Intl to Pensacola

Discover the top 5 airlines that operate flights from O'Hare Intl 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$291FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$378FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$322FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$233Average$410FlexibilityNo 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.