PNS - ORD

$69 Find Cheap Flights from Pensacola to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pensacola to O'Hare Intl departing on 5/21. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pensacola to O'Hare Intl 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.

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Pensacola to O'Hare Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Spirit Airlines Logo
4:35 pm - 11:04 pmPNS-ORD
6h 29m1 stop
Spirit Airlines Logo
5:05 am - 3:30 pmORD-PNS
10h 25m1 stop
$151Spirit Airlines
Find Deal
Wed, May 21 - Tue, May 27
Spirit Airlines Logo
4:35 pm - 11:04 pmPNS-ORD
6h 29m1 stop
Spirit Airlines Logo
12:41 pm - 7:51 pmORD-PNS
7h 10m1 stop
$161Spirit Airlines
Find Deal
Wed, May 7 - Sat, May 10
Delta Logo
11:43 am - 4:59 pmPNS-ORD
5h 16m1 stop
Delta Logo
7:10 am - 12:53 pmORD-PNS
5h 43m1 stop
$197Delta
Find Deal
Thu, Jun 12 - Mon, Jun 16
Delta Logo
7:15 pm - 11:55 pmPNS-ORD
4h 40m1 stop
Delta Logo
9:30 am - 2:24 pmORD-PNS
4h 54m1 stop
$213Delta
Find Deal
Fri, Aug 29 - Wed, Sep 3
American Airlines Logo
9:07 am - 4:05 pmPNS-ORD
6h 58m1 stop
American Airlines Logo
8:15 am - 10:39 amORD-PNS
2h 24mnonstop
$228American Airlines
Find Deal
Thu, May 15 - Sun, May 18
United Airlines Logo
2:05 pm - 4:46 pmPNS-ORD
2h 41mnonstop
United Airlines Logo
10:40 am - 1:08 pmORD-PNS
2h 28mnonstop
$257United Airlines
Find Deal
Wed, May 7 - Sat, May 10
American Airlines Logo
12:07 pm - 2:49 pmPNS-ORD
2h 42mnonstop
American Airlines Logo
5:00 am - 11:52 amORD-PNS
6h 52m1 stop
$269American Airlines
Find Deal
Sun, May 25 - Mon, May 26
Southwest Logo
11:00 am - 4:25 pmPNS-ORD
5h 25m1 stop
Southwest Logo
1:30 pm - 10:00 pmORD-PNS
8h 30m2 stops
$287Southwest
Find Deal
Thu, Jul 17 - Mon, Jul 21
United Airlines Logo
2:05 pm - 4:46 pmPNS-ORD
2h 41mnonstop
United Airlines Logo
10:40 am - 1:07 pmORD-PNS
2h 27mnonstop
$298United Airlines
Find Deal
Wed, May 21 - Sun, May 25
Southwest Logo
6:00 am - 5:55 pmPNS-ORD
11h 55m2 stops
Southwest Logo
1:30 pm - 10:00 pmORD-PNS
8h 30m2 stops
$337Southwest
Find Deal
Thu, Jul 17 - Mon, Jul 21

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

Get data-powered insights and trends into flights from Pensacola to O'Hare Intl 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 Pensacola to Chicago O'Hare Airport?

The average price of all round-trip flights from Pensacola to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago O'Hare Airport on a Thursday and more expensive on a Tuesday. On your return trip to Pensacola, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Chicago O'Hare Intl Airport, 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 Pensacola to Chicago O'Hare Intl Airport is January, where tickets cost $279 (return) on average. On the other hand, the most expensive months are July and September, where the average cost of round-trip tickets is $388 and $387 respectively.

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

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 $406, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Pensacola to Chicago O'Hare Intl Airport, 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 Pensacola to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low season

January

High season

November

Cheapest flight

$69
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Pensacola to Chicago O'Hare Airport

When to book flights from Pensacola to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Pensacola to O'Hare Intl 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 Pensacola to Chicago O'Hare Airport flights

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

    In the last 3 days, the lowest price for a flight from Pensacola to Chicago O'Hare Intl Airport was $69 for a one-way ticket and $151 for a round-trip.

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

    A passport is not required to fly from Pensacola to Chicago O'Hare Airport.

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

    American Airlines, and Delta offer inflight Wi-Fi service on the Pensacola to Chicago O'Hare Airport flight route.

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

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Pensacola to Chicago O'Hare Airport flight route.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Pensacola to Chicago are Delta and Southwest. With an average price for the route of $282 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 $424 and an overall rating of 8.0.

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

    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 Pensacola to Chicago O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Pensacola 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 Pensacola to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport with an airline and back to Pensacola with another airline. Booking your flights between Pensacola and ORD 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 Pensacola to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport from Pensacola up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $164 or less one-way and $300 or less round-trip.

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

Find which airlines fly direct from Pensacola Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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
See more direct flights

Top 5 airlines serving from Pensacola to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Pensacola to Chicago. 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 Pensacola to O'Hare Intl? 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 4280 reviews
8.2Boarding
7.1Food
8.6Crew
8.0Comfort
7.6Entertainment
Airline reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

8.0 ExcellentJames, Feb 2025SRQ - DEN
Read more Southwest reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

The flight was delayed about 20 minutes, but this was an evening flight, so it comes as no surprise. This flight came a good 1.5 days ahead of hurricane Helene which was still far out in the gulf. However, the flight never removed the seated buckle light. The staff announced from the beginning that due to the bad weather (I suppose the hurricane a day and a half away) they would have to do an abbreviated service with water and a snack. I am fine with their water and snack offering, but this was one of the smoothest flights I've had in years. If Southwest believes a flight like this requires everyone to remain seated, then all of their flights should remain buckled for the entire flight. I cannot help but wonder if things like this are a sneaky way to cut back on expenses since the airline is currently under a lot of pressure to reduce costs.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Bad experience. Unhappy with the changing of flight times and one particular flight attendant (Bartholomew) on our flight from Orlando to Detroit. Traveling with a large family of 7, including our 18 month old, can be arduous but when the airline changes your flight time from landing at 9:30 pm to landing after midnight, this becomes much more difficult. When our 18 month old was predictably over tired and fussy, my wife and I tried to move to an open row so we can console her more effectively. The flight attendent rebuked us and said we could not sit in an exit row. We were not planning on sitting there for more than a few minutes but just to have space to console our screaming 18 month old. Spirit did not allow for a family friendly trip. Likely will be choosing a different airline next time.

This flight went flawlessly. I don’t like thei no adjustment seats and them charging for water… but they’re a discount airline so I guess it’s to be expected

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

I upgraded my ticket at the ticket counter and was not informed of the huge bottleneck at TSA pre check. It took me over an hour to get through the line at this small airport and although I ran to the gate and reached it prior to scheduled departure, it had already pushed pack. I missed the flight. Spirit rebooked me on a flight to Orlando that evening, which would require me to then rent a car and drive to FLL. For scheduling reasons, I determined it be would better to rent a car in Pensacola and drive it to my destination in FLL. Spirit called me that evening and asked me if I was going to board the plane. I explained no, for scheduling reasons. The person apologized and said I would receive a refund, but I have not heard back. Certainly, I ought to be refunded the upgrade I paid for at the counter.

Everything was excellent and as expected. The boarding process was great but deboarding was a bit slow. No fault of the crew; it just seemed like the passengers didn’t want to leave! 😂

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