PNS - ORD

$60 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 2/6. 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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Search hundreds of travel sites at once for deals on flights to Chicago O'Hare 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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

Save 23% or moreCompare multiple travel sites with one search.

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Cheap Flight Deals from Pensacola to Chicago O'Hare Airport (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 Chicago O'Hare Airport 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Pensacola to O'Hare Intl.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:17 pm - 12:32 amPNS-ORD
29h 15m1 stop
7:25 am - 6:39 pmORD-PNS
11h 14m1 stop
$148Frontier
Find Deal
Thu, Jan 23 - Fri, Jan 31
10:20 am - 8:13 pmPNS-ORD
9h 53m1 stop
8:00 am - 1:23 pmORD-PNS
5h 23m1 stop
$164Spirit Airlines
Find Deal
Thu, Jan 23 - Tue, Jan 28
10:20 am - 8:13 pmPNS-ORD
9h 53m1 stop
12:25 pm - 6:40 pmORD-PNS
6h 15m1 stop
$174Spirit Airlines
Find Deal
Thu, Jan 23 - Sun, Jan 26
2:36 pm - 5:08 pmPNS-ORD
2h 32mnonstop
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
$209United Airlines
Find Deal
Sat, Jan 11 - Sun, Jan 12
2:36 pm - 5:08 pmPNS-ORD
2h 32mnonstop
3:40 pm - 10:00 pmORD-PNS
6h 20m1 stop
$219United Airlines
Find Deal
Sat, Jan 11 - Wed, Jan 15
1:55 pm - 10:36 pmPNS-ORD
8h 41m1 stop
9:35 am - 1:43 pmORD-PNS
4h 08m1 stop
$238Delta
Find Deal
Mon, Jan 6 - Mon, Jan 13
11:47 am - 4:15 pmPNS-ORD
4h 28m1 stop
5:45 am - 11:27 amORD-PNS
5h 42m1 stop
$273Delta
Find Deal
Tue, Dec 31 - Wed, Jan 8
10:20 am - 10:20 pmPNS-ORD
12h 00m2 stops
7:30 am - 1:45 pmORD-PNS
6h 15m1 stop
$293Southwest
Find Deal
Fri, Feb 14 - Sun, Feb 16
8:20 am - 4:45 pmPNS-ORD
8h 25m1 stop
7:30 am - 5:25 pmORD-PNS
9h 55m2 stops
$303Southwest
Find Deal
Tue, Jan 14 - Wed, Jan 22
5:55 pm - 12:26 amPNS-ORD
6h 31m1 stop
5:02 am - 10:29 amORD-PNS
5h 27m1 stop
$363American Airlines
Find Deal
Thu, Jan 2 - Mon, Jan 6

Flights from Pensacola to O'Hare Intl - Travel Insights & Trends

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 Wednesday and more expensive on a Sunday. On your return trip to Pensacola, you should consider flying back on a Tuesday, and avoid Sundays 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 May, where tickets cost $277 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $384 and $384 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.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $334 on average.

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 6 weeks before departure.

Good to know

Low season

March

High season

November

Cheapest flight

$60
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 13% 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 $60 for a one-way ticket and $148 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?

    WestJet, American Airlines, Delta, and Air Canada 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 Embraer 175 (Enhanced Winglets) 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?

    Star Alliance is the only airline alliance operating flights between Pensacola and Chicago O'Hare Airport.

  • 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Pensacola to Chicago are Delta and United Airlines. With an average price for the route of $282 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $398 and an overall rating of 7.4.

  • 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 $228 or less one-way and $361 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, United Airlines, +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, Emirates, Lufthansa, +1 more

Air New Zealand, Emirates, +2 more

Sunday

Air New Zealand, Emirates, Lufthansa, +1 more

Air New Zealand, Emirates, +2 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, United Airlines

Air New Zealand, United Airlines

Sunday

Air New Zealand, United Airlines

Air New Zealand, United Airlines

See more direct flights
See more direct flights

Top 4 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
DeltaOverall score based on 8601 reviews
8.0Comfort
8.6Crew
7.3Food
8.2Boarding
7.9Entertainment
Airline reviews

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

10.0 ExcellentAllan, Dec 2024MCO - SLC
Read more Delta reviews

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.

I liked the screens in the seat headrest with movies to watch. I didn’t like being forced to check my carryon bag and being told there wasn’t room for my bag - when there were 5 bins sitting empty on takeoff. I didn’t like the “I don’t give a fig” attitude of the flight attendants and the delta gate attendants when I asked why they decided to put me out. They gave me a 1800 number to call but I can’t get a live person on the phone. Customer service is non existent. My business must not be that important to them.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Love delta but the delays and long waits for updates was just too much this time.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

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

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

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.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

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

The people were wonderful, but I hated the way they over charged for luggage, especially for stops which were charged the same as starting point to final destination.

Very mean staff. No entertainment.. No WiFi, a baby cried for over 3 hours no staff offer to assist. My son $500 computer screen got damaged under the plane due to force check in of my bag. TERRIBLE EXPERIENCE!

Nothing I liked. Seats uncomfortable child behind kicking my seat entire flight. Delayed. Couldn't get free glass of water

I did not fly Spirit. Connie used my email while booking her flight. I do not know Connie. It's fraud!!!

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! 😂

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.

Book cheap flights from Pensacola to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Pensacola to Chicago found on KAYAK in the last 72 hours.
2/6Thu
1 stopFrontier
29h 15mPNS-ORD
$60
1/30Thu
1 stopFrontier
29h 15mPNS-ORD
$61
1/24Fri
1 stopSpirit Airlines
9h 53mPNS-ORD
$91
1/18Sat
1 stopSpirit Airlines
9h 53mPNS-ORD
$95
1/21Tue
1 stopDelta
4h 01mPNS-ORD
$114
1/17Fri
1 stopDelta
8h 41mPNS-ORD
$124
1/20Mon
1 stopAmerican Airlines
7h 00mPNS-ORD
$174
1/18Sat
1 stopUnited Airlines
11h 05mPNS-ORD
$188
1/18Sat
2 stopsUnited Airlines
14h 02mPNS-ORD
$193
3/9Sun
1 stopAmerican Airlines
7h 18mPNS-ORD
$209

Search by stops

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Last minute flights from Pensacola to O'Hare Intl

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Pensacola to Chicago that are departing in the next 10 days.
12/25Wed
nonstopUnited Airlines
2h 32mPNS-ORD
1/30Thu
nonstopUnited Airlines
2h 30mORD-PNS
$374
12/24Tue
nonstopUnited Airlines
2h 32mPNS-ORD
1/1Wed
nonstopUnited Airlines
2h 30mORD-PNS
$409
12/24Tue
multi-stopUnited Airlines
8h 06mPNS-ORD
1/1Wed
nonstopUnited Airlines
2h 30mORD-PNS
$419
12/24Tue
multi-stopAmerican Airlines
6h 42mPNS-ORD
1/1Wed
multi-stopAmerican Airlines
5h 27mORD-PNS
$448
12/24Tue
multi-stopAmerican Airlines
5h 31mPNS-ORD
12/29Sun
multi-stopAmerican Airlines
5h 27mORD-PNS
$483
12/25Wed
multi-stopDelta
6h 32mPNS-ORD
12/30Mon
multi-stopDelta
5h 22mORD-PNS
$503
12/22Sun
multi-stop
27h 25mPNS-ORD
1/2Thu
multi-stop
11h 09mORD-PNS
$517
12/22Sun
multi-stop
27h 25mPNS-ORD
1/2Thu
multi-stop
11h 09mORD-PNS
$527
12/22Sun
multi-stopSpirit Airlines
16h 04mPNS-ORD
12/27Fri
multi-stopSpirit Airlines
24h 38mORD-PNS
$956
12/25Wed
multi-stopDelta
7h 50mPNS-ORD
12/30Mon
multi-stopDelta
10h 27mORD-PNS
$2,765

Search by stops

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

Information on your arrival and departure airports

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