CHI - PNS

$79 Find Cheap Flights from Chicago to Pensacola

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Pensacola departing on 7/8. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Pensacola

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola, 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 Chicago to Pensacola, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flights from Chicago to Pensacola (CHI-PNS)

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

Tue, Jul 8 - Sat, Jul 12
Spirit Airlines Logo
10:46 am - 10:37 pmORD-PNS
11h 51m1 stop
Spirit Airlines Logo
6:00 am - 4:57 pmPNS-ORD
10h 57m1 stop
$154Spirit Airlines
Find Deal
Tue, Jul 8 - Sat, Jul 26
Spirit Airlines Logo
10:46 am - 10:37 pmORD-PNS
11h 51m1 stop
Spirit Airlines Logo
6:00 am - 4:57 pmPNS-ORD
10h 57m1 stop
$171Spirit Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 30
United Airlines Logo
10:39 am - 1:06 pmORD-PNS
2h 27mnonstop
United Airlines Logo
2:08 pm - 4:47 pmPNS-ORD
2h 39mnonstop
$277United Airlines
Find Deal
Fri, Jul 18 - Mon, Jul 21
Southwest Logo
1:50 pm - 3:55 pmMDW-PNS
2h 05mnonstop
Southwest Logo
2:25 pm - 4:40 pmPNS-MDW
2h 15mnonstop
$277Southwest
Find Deal
Fri, Jul 18 - Tue, Jul 22
Southwest Logo
1:50 pm - 3:55 pmMDW-PNS
2h 05mnonstop
Southwest Logo
5:30 pm - 11:25 pmPNS-MDW
5h 55m1 stop
$287Southwest
Find Deal
Sun, Jul 13 - Sun, Jul 20
American Airlines Logo
5:15 am - 12:23 pmORD-PNS
7h 08m1 stop
American Airlines Logo
11:19 am - 1:58 pmPNS-ORD
2h 39mnonstop
$287American Airlines
Find Deal
Tue, Jul 8 - Sat, Jul 12
American Airlines Logo
8:30 am - 1:54 pmORD-PNS
5h 24m1 stop
American Airlines Logo
11:36 am - 2:15 pmPNS-ORD
2h 39mnonstop
$294American Airlines
Find Deal
Tue, Oct 14 - Sat, Oct 18
Delta Logo
6:00 am - 12:50 pmORD-PNS
6h 50m1 stop
Delta Logo
11:59 am - 4:38 pmPNS-ORD
4h 39m1 stop
$297Delta
Find Deal
Wed, Jul 9 - Sat, Jul 19
Delta Logo
6:00 am - 10:38 amMDW-PNS
4h 38m1 stop
Delta Logo
6:00 am - 9:45 amPNS-MDW
3h 45m1 stop
$297Delta
Find Deal
Fri, Aug 22 - Thu, Aug 28
United Airlines Logo
10:53 am - 1:18 pmORD-PNS
2h 25mnonstop
United Airlines Logo
2:15 pm - 4:52 pmPNS-ORD
2h 37mnonstop
$300United Airlines
Find Deal
Useful Info

KAYAK's insights & trends for Chicago to Pensacola flights

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

Find cheap flights to Pensacola
Find cheap flights to Pensacola

Planning a trip from Chicago to Pensacola? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the cheapest Chicago to Pensacola flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Pensacola.

Our data shows that the cheapest route for a return flight from Chicago to Pensacola cost $150 and was between Chicago Midway Airport (MDW) and Pensacola (PNS). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $150.

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

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

For Chicago to Pensacola, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Pensacola back to Chicago, the best deals are generally found on Thursday, with Tuesday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Pensacola, 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 Chicago to Pensacola is January, where tickets cost $298 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $429 and $396 respectively.

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

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 $635, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Pensacola, 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 Chicago to Pensacola, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonJanuary
High seasonMarch
Cheapest flight$79
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to Pensacola

When to book flights from Chicago to Pensacola

Are your dates flexible? Find out the best times to travel from Chicago to Pensacola 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 flights from Chicago to Pensacola

  • Is Chicago O' Hare International Airport (ORD) a hub for any airline on this route?

    This airport is a large hub for United Airlines. That means you will find five lounges offered by this airline at this airport. With the large number of flights they offer from this airport, you should have plenty of options in case of any issues with your original flight.

  • Are there any other airports that I can fly to on this route?

    The Mobile Regional Airport (MOB) is just a short trip to the west of downtown Pensacola. You can travel on one-stop flights from Chicago O' Hare International Airport (ORD) aboard Delta Air Lines to this airport and then take the Omnibus Express Houston Line that can get you to Pensacola in about 1 h 10 min.

  • Do any airlines on this route offer a service for kids flying alone?

    Delta Air Lines provides a specialized Unaccompanied Minor service, ensuring the safe travel of children who are flying alone. During the check-in process, a valid identification document must be presented, and upon arrival at the destination, the designated person meeting the child will be required to provide a signature for verification. Throughout the flight, Delta Air Lines takes every precaution to ensure your child's safety, comfort, and a positive travel experience.

  • Is there anything I can do with my kids at Chicago O' Hare International Airport (ORD)?

    Situated in Terminal Two beyond the security checkpoint, the Family Lounge at O'Hare Airport provides a dedicated area for kids to enjoy and play. The space is adorned with vibrant seating and convenient device charging stations. For families traveling with infants, there's a designated stroller parking area as well. At different times throughout the year, especially during the holiday season, visitors can enjoy live entertainment that includes performances by musicians, caricature artists, and other delightful acts.

  • What is the cheapest flight from Chicago to Pensacola?

    In the last 3 days, the lowest price for a flight from Chicago to Pensacola was $79 for a one-way ticket and $154 for a round-trip.

  • Do I need a passport to fly between Chicago and Pensacola?

    No, a passport isn't needed to fly from Chicago to Pensacola. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Pensacola?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Pensacola.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Pensacola?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Pensacola flight route.

  • Which aircraft models fly most regularly from Chicago to Pensacola?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Chicago to Pensacola flight route.

  • Which airline alliances offer flights from Chicago to Pensacola?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Pensacola, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Pensacola?

    There are nonstop flights from Chicago to Pensacola on a daily basis.

  • Which is the best airline for flights from Chicago to Pensacola, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Pensacola are Southwest and Delta. With an average price for the route of $395 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $305 and an overall rating of 8.0.

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

    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 Chicago to Pensacola.

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

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

    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 Pensacola with an airline and back to Chicago with another airline.

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

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

KAYAK’s top tips for finding a cheap flight from Chicago to Pensacola

  • Looking for a cheap flight? 25% of our users found flights on this route for $138 or less one-way and $268 or less round-trip.
  • When you want an easier way to get to Chicago Midway International Airport (MDW), you might consider taking the Chicago Transit Authority Orange Line that travels from the Adams/Wabash Station to the airport in about 23 minutes.
  • Since there are no direct flights on this route, some of the layover airports you can expect to use include Fort Lauderdale International Airport (FLL), Charlotte Douglas International Airport (CLT), and Orlando International Airport (MCO).
  • For passengers traveling with Spirit Airlines, it is crucial to adhere to the carry-on bag size restrictions, which must not exceed the maximum dimensions of 22 x 18 x 10 inches. Keep in mind that Spirit Airlines retains the authority to request the checking of a carry-on bag if it cannot be securely stowed on a particular flight.
  • Frontier Airlines imposes specific guidelines for checked bags. Your checked baggage should not exceed 62 linear inches and should weigh no more than 40 lb. Anything above this will result in an additional charge. Bags exceeding 110 linear inches will not be accepted for check-in.
  • American Airlines permits passengers to bring one golf bag, which can include golf clubs, golf balls, golf tees, and one pair of golf shoes. Bags can weigh up to 50 lb. and measure up to 126 inches in total dimensions. There may be a fee for taking golf clubs based on your ticket tier.

Prefer to fly direct from Chicago to Pensacola?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Pensacola.
Find which airlines fly direct from Chicago to Pensacola Airport, which days they fly and book direct flights.

Direct departures

Chicago to Pensacola

Monday

Southwest, United Airlines

Southwest, United Airlines

Tuesday

Southwest, United Airlines

Southwest, United Airlines

Wednesday

Southwest, United Airlines

Southwest, United Airlines

Thursday

Southwest, United Airlines

Southwest, United Airlines

Friday

Southwest, United Airlines

Southwest, United Airlines

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Direct returns

Pensacola to Chicago

Monday

Southwest, United Airlines

Southwest, United Airlines

Tuesday

Southwest, United Airlines

Southwest, United Airlines

Wednesday

Southwest, United Airlines

Southwest, United Airlines

Thursday

Southwest, United Airlines

Southwest, United Airlines

Friday

Southwest, United Airlines

Southwest, United Airlines

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Pensacola

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Pensacola. 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 Chicago to Pensacola? 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 4278 reviews
8.6Crew
7.1Food
8.2Boarding
7.6Entertainment
8.0Comfort
Airline reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

6.0 GoodVincent, May 2025MDW - MCO
Read more Southwest reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

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

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

My experience with spirit was terrible. Customer service was terrible. Flight got canceled abruptly with no accommodations made for the inconvenience or any sort of help. I was unable to rebook a new flight.

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.