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Cheap Flights from Pensacola to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Chicago
Chicago1 stop$214
Moline
Moline1 stop$339
Peoria
Peoria1 stop$326
Paducah
Paducah1 stop$418
Chicago
Chicago1 stop$214
Moline
Moline1 stop$339
Peoria
Peoria1 stop$326
Paducah
Paducah1 stop$418
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?

Flight prices are below average for this route right now.

Flights to Illinois from Pensacola usually cost between $284 and $541 in November.
The lowest price found in the past 5 days was $214 on Frontier (Nov 24-Nov 27).

What is the cheapest Pensacola to Illinois flight route?

The cheapest ticket to Illinois from Pensacola found in the last 5 days was to Chicago, at $319 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 5 days was $319.

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

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $459 on average. Morning departures are around 9% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $504.

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

No, with an average price for the route of $408, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Pensacola to Illinois is February, when tickets cost $279 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $446 and $415 respectively.

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

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

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

To get a below average price on the flight from Pensacola to Illinois, you should book around 3 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low season

September

Cheapest flight

$98
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 11% increase in price.
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.

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 $224 one-way - $394 round-trip; St. Louis $262 one-way - $296 round-trip

Reviews of the top 5 airlines serving from Pensacola to Illinois

 
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.
7.9
SouthwestOverall score based on 4217 reviews
7.4Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

10.0 ExcellentLaura, Sep 2026
Read more Southwest reviews

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

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.

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.

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

The flight was great. We were not offered any beverages though. And there was no real turbulence, so not sure why.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Requested an aisle seat at the gate and got it. The staff so friendly

Flight was very delayed so I was able to get on an earlier flight via stand-by. Crew communicated effectively around delay and worked to make customers comfortable. Wifi was ok, streaming TV was great. App functionality broke down once I was moved to stand-by on earlier flight.

Sat in the tarmac at O’Hare for 65 minutes. This is a regular occurrence for delta at O’Hare

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

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.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

The price. Omg $1100. Was crazy and it was not clear on the website.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

The flight attendant was very kind and offered my son a snack for free.

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Horrible airline! They always got something messed up with their planes. 3 hour delayed made us missed both out flights. Had to wake up early in the morning next morning to get another flight!

Took off over an hour late with multiple mechanical issues. Gate agent in Dallas was lazy and was slow as molasses. Had a line 10 people long. Spirit bad..

The flight was great until towards the end when the flight attendant read an excessively long commercial for purchasing an american airlines credit card. The worst part is that we are doing a lot of traveling this year so i was actually interested in getting the credit card, but I was so annoyed with the long commercial that I completely dismissed the flight attendant bringing around the information. Next time, keep the sales pitch to 10 seconds and then pass around the brochures!!

Me and my husband experienced very bad in American Airlines. We missed our flight going to Doha. The American Airlines was delayed we arrived already 10:27pm. Supposed to be 9:40 pm. So what they did they rebooked our flight and they gave us a hotel. When we arrived at the hotel the front desk said it was fully booked already. Oh my gosh! I said why did you accept the booking if it's fully booked. The guy said that's American Airlines they just book even it's already full. That's 2am already, we have nothing to do so, we decided to go another hotel. We pay the room, food and taxi. Pls give an action on this matter. Refund our expenses and give us more compensation. Not only our room, food, taxi but also our efforts, tiredness looking for a room that can accommodate us.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Severe turbulence. Captain never came on to reassure passengers after things settled down.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

The trip was unremarkable which is good. Crew was very professional and courteous.

More options for your flight from Pensacola to Illinois

Complete your trip to Illinois with a hotel stay or car rental