$90 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 4/9. 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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Flight Deals

Cheap Flights from Pensacola to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$183
Moline
Moline1 stop$309
Peoria
Peoria1 stop$309
St. Louis
St. Louis1 stop$213
Paducah
Paducah2 stops$449
Chicago
Chicago1 stop$183
Moline
Moline1 stop$309
Peoria
Peoria1 stop$309
St. Louis
St. Louis1 stop$213
Paducah
Paducah2 stops$449

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

Thu, Apr 16 - Sun, Apr 19
Frontier Logo
3:25 pm - 7:59 am
PNS
-
MDW
16h 34m
1 stop
Frontier Logo
9:04 am - 9:17 am
MDW
-
PNS
24h 13m
1 stop
$183Frontier
Wed, Apr 8 - Sat, Apr 11
Spirit Airlines Logo
2:15 pm - 7:51 pm
PNS
-
ORD
5h 36m
1 stop
Spirit Airlines Logo
12:45 pm - 9:14 pm
ORD
-
PNS
8h 29m
1 stop
$184Spirit Airlines
Wed, Jul 22 - Tue, Jul 28
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
12:55 pm - 3:05 pm
MDW
-
PNS
2h 10mnonstop
$247Southwest
Thu, Apr 9 - Sun, Apr 12
Southwest Logo
9:55 am - 3:15 pm
PNS
-
MDW
5h 20m
1 stop
Southwest Logo
8:25 am - 10:40 am
MDW
-
PNS
2h 15mnonstop
$257Southwest
Wed, May 13 - Sat, May 16
Delta Logo
6:01 pm - 11:59 pm
PNS
-
STL
5h 58m
1 stop
Delta Logo
5:15 pm - 11:16 pm
STL
-
PNS
6h 01m
1 stop
$281Delta
Fri, May 8 - Sun, May 10
American Airlines Logo
4:31 pm - 10:05 pm
PNS
-
MLI
5h 34m
1 stop
American Airlines Logo
3:48 pm - 10:25 pm
MLI
-
PNS
6h 37m
1 stop
$309American Airlines
Wed, Apr 15 - Sun, Apr 19
American Airlines Logo
3:01 pm - 11:13 pm
PNS
-
PIA
8h 12m
1 stop
American Airlines Logo
6:00 am - 12:42 pm
PIA
-
PNS
6h 42m
1 stop
$309American Airlines
Fri, May 22 - Tue, May 26
Delta Logo
4:35 pm - 10:21 pm
PNS
-
MLI
5h 46m
1 stop
Delta Logo
5:17 pm - 11:16 pm
MLI
-
PNS
5h 59m
1 stop
$364Delta
Fri, May 29 - Thu, Jun 11
United Airlines Logo
2:04 pm - 7:26 pm
PNS
-
PIA
5h 22m
1 stop
United Airlines Logo
8:20 am - 1:02 pm
PIA
-
PNS
4h 42m
1 stop
$379United Airlines
Wed, Apr 15 - Sat, Apr 18
United Airlines Logo
2:15 pm - 9:13 pm
PNS
-
PIA
6h 58m
1 stop
United Airlines Logo
10:40 am - 9:57 pm
PIA
-
PNS
11h 17m
2 stops
$384United 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 $207 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 $207.

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

The average price for all round-trip flights from Pensacola to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $407 on average. Morning departures are around 18% 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 $500.

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 $287, 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 $273 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $352 and $350 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 Sunday, as it's usually the priciest day. When flying back from Illinois, Wednesday 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 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 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$90
Best time to beat the crowds with an average 13% drop 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.

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 $158 one-way - $282 round-trip; Chicago $169 one-way - $308 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 4318 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

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.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

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

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

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

The flight was great as well as the airline staff

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

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

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.

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

Information on your arrival and departure airports