ORD - PNS

$60 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 2/28. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$209
Overall average: $318
Multiple Airlines
Thu 2/12Tue 2/17
ORD - PNS • 1 stop
Cheapest non-stop
$217
Typical prices: $271-$553
United Airlines
Fri 3/6Sun 3/8
ORD - PNS • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Main Cabin Extra includes early boarding.
Spirit's Big Front Seat adds 11 inches more legroom.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from $227 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 21% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 10% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pensacola!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

Thu, Feb 12 - Tue, Feb 17
Multiple Airlines Logo
4:16 pm - 6:15 pm
ORD
-
PNS
25h 59m
1 stop
Multiple Airlines Logo
5:20 pm - 11:47 pm
PNS
-
ORD
6h 27m
1 stop
$209Multiple Airlines
Mon, Feb 9 - Thu, Feb 19
Spirit Airlines Logo
10:48 am - 4:37 pm
ORD
-
PNS
5h 49m
1 stop
Spirit Airlines Logo
5:20 pm - 11:22 am
PNS
-
ORD
18h 02m
1 stop
$210Spirit Airlines
Tue, Feb 10 - Wed, Feb 18
Spirit Airlines Logo
10:48 am - 4:37 pm
ORD
-
PNS
5h 49m
1 stop
Spirit Airlines Logo
5:20 pm - 7:54 am
PNS
-
ORD
14h 34m
2 stops
$211Spirit Airlines
Wed, Feb 11 - Wed, Feb 18
Multiple Airlines Logo
10:48 am - 4:37 pm
ORD
-
PNS
5h 49m
1 stop
Multiple Airlines Logo
6:37 pm - 10:46 am
PNS
-
ORD
16h 09m
1 stop
$212Multiple Airlines
Thu, Jan 29 - Mon, Feb 2
Spirit Airlines Logo
7:20 am - 3:08 pm
ORD
-
PNS
7h 48m
1 stop
Spirit Airlines Logo
4:03 pm - 11:47 pm
PNS
-
ORD
7h 44m
1 stop
$213Spirit Airlines
Sat, Feb 14 - Wed, Feb 18
Spirit Airlines Logo
5:15 am - 3:54 pm
ORD
-
PNS
10h 39m
1 stop
Spirit Airlines Logo
5:20 pm - 11:22 am
PNS
-
ORD
18h 02m
1 stop
$214Spirit Airlines
Wed, Apr 1 - Tue, Apr 7
Spirit Airlines Logo
7:17 am - 1:24 pm
ORD
-
PNS
6h 07m
1 stop
Spirit Airlines Logo
2:24 pm - 11:17 pm
PNS
-
ORD
8h 53m
1 stop
$215Spirit Airlines
Sat, Feb 14 - Wed, Feb 25
Spirit Airlines Logo
7:00 am - 3:54 pm
ORD
-
PNS
8h 54m
1 stop
Spirit Airlines Logo
5:20 pm - 11:22 am
PNS
-
ORD
18h 02m
1 stop
$216Spirit Airlines
Wed, Feb 18 - Thu, Feb 26
Spirit Airlines Logo
7:00 am - 3:54 pm
ORD
-
PNS
8h 54m
1 stop
Spirit Airlines Logo
6:37 pm - 11:22 am
PNS
-
ORD
16h 45m
2 stops
$217Spirit Airlines
Tue, Feb 17 - Wed, Feb 18
Spirit Airlines Logo
10:44 am - 5:42 pm
ORD
-
PNS
6h 58m
1 stop
Spirit Airlines Logo
5:20 pm - 7:54 am
PNS
-
ORD
14h 34m
2 stops
$218Spirit Airlines
Booking Insights

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 November, where tickets cost $298 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $374 and $368 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.

No, with an average price for the route of $379, prices are generally cheapest when you fly direct.

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, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from O'Hare Intl to Pensacola

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


United's Priority Boarding can help secure overhead bin space, placing you in Zone 2.

American Airlines

American's Main Cabin Extra provides early boarding and complimentary alcoholic drinks.


American's Wi-Fi offers 20 minutes free with an ad, useful for quick tasks.

Spirit Airlines

Spirit's Big Front Seat offers 20-inch width and 11 inches more legroom.


Spirit's Wi-Fi offers gate-to-gate connectivity, with browsing and streaming packages.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Read more

Good to know

Low seasonJanuary
Cheapest flight$60
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 13% 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 $60 for a one-way ticket and $209 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 Embraer 175 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and Pensacola, with SkyTeam 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Pensacola are Southwest and Delta. With an average price for the route of $348 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $263 and an overall rating of 7.9.

  • 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 $163 or less one-way and $316 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

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Pensacola to Chicago O'Hare Intl

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

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 4258 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

10.0 ExcellentManetta, Jan 2026
MDW - CLT
Read more Southwest reviews

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

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

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

Second time in 3 days I walked off the plane late. This time - almost an hour.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Your flight crew and boarding area crew need to have microphone use training. They all hold the microphone right up to their mouths, way to close making understanding them almost impossible. The microphone should be held about 3 to 4 inches away from their mouths. This would provide for much better clarity through the PA system. ‘Eating the mic’ DOES NOT work.

It was the first time I flew on that airline and had a very positive experience. Nearly identical to Jetblue which consider the standard of airlines excellence.

A bottled or canned drink, whether water or soda would have been appreciated upon settling in and flying, without being charged for it.

COMMUNICATION!!!! The issue was a crew shortage, which means you knew in advance the issue. Instead of notifying people in advance, we're finding out an hour before the flight it's canceled. You rebooked people to more flights you knew wouldn't get out. You ended by taking part of my party to a completely different state and leaving them there. The next morning, you still have no way to get them to the original destination and they ended up missing an important event. We came out of so much money to check bags multiple times. And on top of all that, the staff in the building seemed to not care and were fairly rude. Overall, just go on and fold and quit making promises to people to get them places when you know you can't. Shoutout to Delta for doing a great job at making it less painful (for those of us who made it).

The flight was cancelled without prior notice. I was inform as I was checking in. No hotel accommodation nor any simple explanation as why it was cancelled.

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Bad experience with gate agent. I asked what group she was boarding. She gave me a face and said, with attitude, group 1. I stood back and waited for my group, group 2 to be called. After an awful lot of people boarded she took the mic and announced, now boarding group 5. The lack of professionalism amongst spirit staff is astounding.

Boarding process was slightly delayed but took an extra long time which caused a 30 minutes delay.

Everything you need to know for your flight from O'Hare Intl to Pensacola

Information on your arrival and departure airports