$60 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 2/27. 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 Illinois

 
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
Chicago2 stops$163
Moline
Moline1 stop$279
Peoria
Peoria1 stop$279
St. Louis
St. Louis1 stop$143
Chicago
Chicago2 stops$163
Moline
Moline1 stop$279
Peoria
Peoria1 stop$279
St. Louis
St. Louis1 stop$143

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

mar., févr. 24 - mar., mars 3
Multiple Airlines Logo
6:37 pm - 10:27 pm
PNS
-
STL
27h 50m
1 stop
Multiple Airlines Logo
3:49 pm - 5:42 pm
STL
-
PNS
25h 53m
1 stop
$143Multiple Airlines
mar., févr. 24 - mar., mars 3
Multiple Airlines Logo
6:37 pm - 12:40 am
PNS
-
ORD
30h 03m
2 stops
Multiple Airlines Logo
8:30 am - 5:42 pm
ORD
-
PNS
9h 12m
1 stop
$163Multiple Airlines
sam., févr. 14 - mer., févr. 18
Spirit Airlines Logo
5:20 pm - 11:47 pm
PNS
-
ORD
6h 27m
1 stop
Spirit Airlines Logo
12:44 pm - 5:42 pm
ORD
-
PNS
4h 58m
1 stop
$167Spirit Airlines
jeu., mars 5 - mar., mars 10
Southwest Logo
5:25 pm - 7:40 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
12:15 pm - 2:25 pm
MDW
-
PNS
2h 10mnonstop
$207Southwest
jeu., mars 5 - mar., mars 10
Southwest Logo
7:10 am - 11:55 am
PNS
-
MDW
4h 45m
1 stop
Southwest Logo
12:15 pm - 2:25 pm
MDW
-
PNS
2h 10mnonstop
$217Southwest
jeu., mars 5 - mar., mars 10
Delta Logo
1:37 pm - 5:45 pm
PNS
-
MDW
4h 08m
1 stop
Delta Logo
12:47 pm - 7:01 pm
MDW
-
PNS
6h 14m
1 stop
$227Delta
mer., févr. 11 - dim., févr. 15
American Airlines Logo
4:15 pm - 9:43 pm
PNS
-
PIA
5h 28m
1 stop
American Airlines Logo
5:00 am - 10:21 am
PIA
-
PNS
5h 21m
1 stop
$279American Airlines
jeu., févr. 12 - lun., févr. 16
Delta Logo
9:25 am - 4:16 pm
PNS
-
MLI
6h 51m
1 stop
Delta Logo
5:01 pm - 11:11 pm
MLI
-
PNS
6h 10m
1 stop
$279Delta
mer., févr. 11 - dim., févr. 15
American Airlines Logo
6:05 am - 3:24 pm
PNS
-
PIA
9h 19m
2 stops
American Airlines Logo
5:00 am - 10:21 am
PIA
-
PNS
5h 21m
1 stop
$284American Airlines
jeu., févr. 12 - lun., févr. 16
United Airlines Logo
2:10 pm - 7:02 pm
PNS
-
MLI
4h 52m
1 stop
United Airlines Logo
10:46 am - 8:15 pm
MLI
-
PNS
9h 29m
2 stops
$397United Airlines
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.

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 $331, 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 February, when tickets cost $228 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is $394 and $351 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 Fridays 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 Saturday 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 3 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$60
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Pensacola to St. Louis

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 in the morning, when round-trip flights cost $393 on average. Morning departures are around 4% cheaper 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 $426.

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 $185 one-way - $318 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 4267 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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.

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

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

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

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

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

Everything you need to know for your flight from Pensacola to Illinois

Information on your arrival and departure airports