ORD - PNS

$57 Find Cheap Flights from Chicago O'Hare Airport to Pensacola

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Pensacola departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Pensacola

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola, as well as popular online travel agencies
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Cheap Flights from O'Hare Intl to Pensacola (ORD-PNS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Pensacola that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Pensacola

Tue, Aug 12 - Tue, Aug 19
United Airlines Logo
10:39 am - 1:06 pmORD-PNS
2h 27mnonstop
United Airlines Logo
2:15 pm - 4:52 pmPNS-ORD
2h 37mnonstop
$133United Airlines
Find Deal
Mon, Aug 11 - Tue, Aug 19
United Airlines Logo
10:39 am - 1:06 pmORD-PNS
2h 27mnonstop
United Airlines Logo
2:15 pm - 4:52 pmPNS-ORD
2h 37mnonstop
$153United Airlines
Find Deal
Tue, Aug 12 - Tue, Aug 19
Southwest Logo
3:10 pm - 6:55 pmORD-PNS
3h 45m1 stop
Southwest Logo
7:35 am - 5:55 pmPNS-ORD
10h 20m2 stops
$158Southwest
Find Deal
Tue, Aug 12 - Tue, Aug 19
Southwest Logo
6:00 am - 3:35 pmORD-PNS
9h 35m2 stops
Southwest Logo
11:20 am - 11:05 pmPNS-ORD
11h 45m2 stops
$163Southwest
Find Deal
Tue, Jul 22 - Thu, Jul 24
Spirit Airlines Logo
4:36 pm - 10:41 pmORD-PNS
6h 05m1 stop
Spirit Airlines Logo
6:00 am - 3:31 pmPNS-ORD
9h 31m1 stop
$168Spirit Airlines
Find Deal
Tue, Aug 5 - Thu, Aug 7
Spirit Airlines Logo
4:36 pm - 10:41 pmORD-PNS
6h 05m1 stop
Spirit Airlines Logo
6:00 am - 3:31 pmPNS-ORD
9h 31m1 stop
$171Spirit Airlines
Find Deal
Tue, Aug 12 - Fri, Aug 22
Delta Logo
7:05 am - 1:08 pmORD-PNS
6h 03m1 stop
Delta Logo
5:59 pm - 11:56 pmPNS-ORD
5h 57m1 stop
$177Delta
Find Deal
Tue, Aug 5 - Sun, Aug 10
Delta Logo
7:00 am - 12:49 pmORD-PNS
5h 49m1 stop
Delta Logo
6:03 pm - 12:09 amPNS-ORD
6h 06m1 stop
$185Delta
Find Deal
Mon, Aug 11 - Mon, Aug 18
 Logo
5:40 am - 3:34 pmORD-PNS
9h 54m1 stop
 Logo
4:52 pm - 11:59 pmPNS-ORD
7h 07m1 stop
Thu, Oct 16 - Sun, Oct 19
 Logo
6:00 am - 3:31 pmORD-PNS
9h 31m1 stop
 Logo
8:46 am - 2:34 pmPNS-ORD
5h 48m1 stop
Useful Info

KAYAK's insights & trends for O'Hare Intl to Pensacola flights

Get data-powered insights and trends into flights from O'Hare Intl to Pensacola to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Pensacola?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Pensacola clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago O'Hare Airport to Pensacola, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Pensacola, Thursday is the cheapest day to fly and Tuesday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Pensacola, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Pensacola is January, where tickets cost $291 (return) on average. On the other hand, the most expensive months are August and December, where the average cost of round-trip tickets is $421 and $418 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Pensacola?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $629 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Pensacola, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Pensacola, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonJanuary
High seasonMarch
Cheapest flight$57
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago O'Hare Airport to Pensacola

When to book flights from O'Hare Intl to Pensacola

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Pensacola based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to Pensacola flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Pensacola?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Pensacola was $57 for a one-way ticket and $133 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Pensacola?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago O'Hare Airport to Pensacola?

    When flying out of Chicago O'Hare Airport you will be using Chicago O'Hare Intl. You will be landing at Pensacola, also known as Pensacola.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Pensacola?

    Only American Airlines offers inflight Wi-Fi service on the Chicago O'Hare Airport to Pensacola flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Pensacola?

    The Airbus A319 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Pensacola flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Pensacola?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and Pensacola, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago O'Hare Airport to Pensacola?

    There are nonstop flights from Chicago O'Hare Airport to Pensacola on a daily basis.

  • Which is the best airline for flights from Chicago to Pensacola, Delta or Southwest?

    The two airlines most popular with KAYAK users for flights from Chicago to Pensacola are Delta and Southwest. With an average price for the route of $297 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $378 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Pensacola?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Pensacola.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Pensacola?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pensacola from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Pensacola?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Pensacola with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and PNS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Pensacola?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Pensacola from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Pensacola

  • Looking for a cheap flight? 25% of our users found flights on this route for $203 or less one-way and $301 or less round-trip.

Prefer to fly direct from Chicago O'Hare Airport to Pensacola?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Pensacola.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Pensacola Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Pensacola

Monday

Air New Zealand, United Airlines

Air New Zealand, United Airlines

Tuesday

Air New Zealand, United Airlines

Air New Zealand, United Airlines

Wednesday

Air New Zealand, United Airlines

Air New Zealand, United Airlines

Thursday

Air New Zealand, United Airlines

Air New Zealand, United Airlines

Friday

Air New Zealand, United Airlines

Air New Zealand, United Airlines

Saturday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

Sunday

Air New Zealand, American Airlines, United Airlines

Air New Zealand, American Airlines, +1 more

See more direct flights

Direct returns

Pensacola to Chicago O'Hare Intl

Monday

Air New Zealand, Emirates, Lufthansa, +1 more

Air New Zealand, Emirates, +2 more

Tuesday

Air New Zealand, Emirates, Lufthansa, +1 more

Air New Zealand, Emirates, +2 more

Wednesday

Air New Zealand, Emirates, Lufthansa, +1 more

Air New Zealand, Emirates, +2 more

Thursday

Air New Zealand, Emirates, Lufthansa, +1 more

Air New Zealand, Emirates, +2 more

Friday

Air New Zealand, Emirates, Lufthansa, +1 more

Air New Zealand, Emirates, +2 more

Saturday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Sunday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

See more direct flights

Reviews of the top 5 airlines serving from O'Hare Intl to Pensacola

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Pensacola. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Pensacola? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4252 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.6Entertainment
Airline reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

I am very happy with my experience with Spirit Airlines. Both flights were on time. Boarding was very pleasant. Crew was very nice. Flights were amazing and we even arrived earlier than the schedule time. I am hoping Spirits keeps on having non stop flight from Ft Lauderdale to Hartford for many years to come.

you guys canceled my flight last minute and lost my luggage.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

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