$55 Find Cheap Flights from Pensacola to Illinois

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 Illinois departing on 11/17. 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

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pensacola to Illinois, 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 Illinois, as well as popular online travel agencies
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Cheap Flights from Pensacola to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$209
Moline
Moline1 stop$249
Peoria
Peoria1 stop$279
St. Louis
St. Louis1 stop$175
Paducah
Paducah1 stop$304
Chicago
Chicagononstop$209
Moline
Moline1 stop$249
Peoria
Peoria1 stop$279
St. Louis
St. Louis1 stop$175
Paducah
Paducah1 stop$304

Book Cheap Pensacola to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pensacola to Illinois 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 Pensacola to Illinois

Sun, Nov 9 - Thu, Nov 13
Frontier Logo
4:45 pm - 9:07 amPNS-STL
16h 22m1 stop
Frontier Logo
7:45 pm - 3:35 pmSTL-PNS
19h 50m1 stop
$175Frontier
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Wed, Dec 3 - Sun, Dec 14
United Airlines Logo
2:15 pm - 4:47 pmPNS-ORD
2h 32mnonstop
United Airlines Logo
10:50 am - 1:16 pmORD-PNS
2h 26mnonstop
$209United Airlines
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Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
1:16 pm - 3:55 pmPNS-ORD
2h 39mnonstop
American Airlines Logo
8:25 am - 10:47 amORD-PNS
2h 22mnonstop
$213American Airlines
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Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
1:16 pm - 3:55 pmPNS-ORD
2h 39mnonstop
American Airlines Logo
8:25 am - 10:47 amORD-PNS
2h 22mnonstop
$214American Airlines
Find Deal
Wed, Nov 12 - Thu, Nov 20
Spirit Airlines Logo
8:16 pm - 11:12 amPNS-ORD
14h 56m1 stop
Spirit Airlines Logo
10:12 am - 7:11 pmORD-PNS
8h 59m1 stop
$218Spirit Airlines
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Thu, Dec 4 - Mon, Dec 8
Southwest Logo
4:15 pm - 8:15 pmPNS-MDW
4h 00m1 stop
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
$224Southwest
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Fri, Feb 6 - Mon, Feb 9
Spirit Airlines Logo
6:49 pm - 3:55 pmPNS-ORD
21h 06m2 stops
Spirit Airlines Logo
5:05 am - 3:36 pmORD-PNS
10h 31m1 stop
$228Spirit Airlines
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Mon, Jan 12 - Tue, Jan 13
Southwest Logo
4:00 pm - 9:55 pmPNS-STL
5h 55m1 stop
Southwest Logo
8:55 am - 3:15 pmSTL-PNS
6h 20m1 stop
$229Southwest
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Tue, Mar 10 - Wed, Mar 11
Delta Logo
6:00 am - 9:56 amPNS-MDW
3h 56m1 stop
Delta Logo
1:05 pm - 6:03 pmMDW-PNS
4h 58m1 stop
$229Delta
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Mon, Nov 24 - Sat, Nov 29
Delta Logo
7:09 pm - 12:02 amPNS-ORD
4h 53m1 stop
Delta Logo
5:23 am - 10:41 amORD-PNS
5h 18m1 stop
$229Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Pensacola to Illinois flights

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

How much is a round-trip flight from Pensacola to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Pensacola to Illinois departing in December.

What is the cheapest Pensacola to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Pensacola found in the last 72 hours was to Chicago, at $209 round-trip. The most popular route is from Pensacola (PNS) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $209.

Can I save money by flying with a layover from Pensacola to Illinois?

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 $298, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Pensacola to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Illinois, 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 Illinois is November, when tickets cost $267 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $414 and $353 respectively.

What’s the cheapest day of the week to fly from Pensacola to Illinois?

The average price of all round-trip flights from Pensacola to Illinois clicked on KAYAK for each day over the last 12 months.

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

How far in advance should I book a flight from Pensacola to Illinois?

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 Illinois, 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 Illinois, you should book around 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$55
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Pensacola to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Pensacola to Illinois?

    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 Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pensacola to Illinois 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 Illinois?

    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 from Pensacola to Illinois with an airline and back with another airline.

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

    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 from Pensacola to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $307 on average. Morning departures are around 20% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $448.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Pensacola to the following destinations at these prices or less: Chicago $125 one-way - $258 round-trip; St. Louis $201 one-way - $322 round-trip

Reviews of the top 5 airlines serving from Pensacola to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Pensacola to Illinois. 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 Illinois? 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 4241 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

10.0 ExcellentMelissa, Sep 2025MSY - MDW
Read more Southwest reviews

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

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.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Cramped seating for me. Luckily it wasn’t a long flight

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

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.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

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