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 9/2. 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

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola.
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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

Mon, Aug 18 - Sat, Aug 23
Spirit Airlines Logo
10:26 am - 3:57 pmORD-PNS
5h 31m1 stop
Spirit Airlines Logo
9:14 am - 7:07 pmPNS-ORD
9h 53m1 stop
$160Spirit Airlines
Find Deal
Mon, Aug 18 - Sat, Aug 23
Spirit Airlines Logo
5:05 am - 3:57 pmORD-PNS
10h 52m1 stop
Spirit Airlines Logo
9:14 am - 7:07 pmPNS-ORD
9h 53m1 stop
$168Spirit Airlines
Find Deal
Wed, Nov 19 - Mon, Nov 24
American Airlines Logo
10:30 am - 1:00 pmORD-PNS
2h 30mnonstop
American Airlines Logo
1:17 pm - 3:55 pmPNS-ORD
2h 38mnonstop
$209American Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
Southwest Logo
8:20 am - 10:30 amMDW-PNS
2h 10mnonstop
Southwest Logo
4:45 pm - 6:55 pmPNS-MDW
2h 10mnonstop
$217Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Frontier Logo
7:00 am - 3:05 pmORD-PNS
8h 05m1 stop
Frontier Logo
4:00 pm - 11:39 pmPNS-ORD
7h 39m1 stop
$218Frontier
Find Deal
Wed, Nov 19 - Mon, Nov 24
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
Southwest Logo
5:30 pm - 11:30 pmPNS-MDW
6h 00m1 stop
$224Southwest
Find Deal
Sat, Sep 13 - Fri, Sep 19
Frontier Logo
8:25 am - 4:26 pmORD-PNS
8h 01m1 stop
Frontier Logo
5:21 pm - 11:59 pmPNS-ORD
6h 38m1 stop
$228Frontier
Find Deal
Wed, Nov 19 - Mon, Nov 24
Delta Logo
7:10 am - 12:50 pmORD-PNS
5h 40m1 stop
Delta Logo
5:45 pm - 11:53 pmPNS-ORD
6h 08m1 stop
$229Delta
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
6:00 am - 10:50 amMDW-PNS
4h 50m1 stop
Delta Logo
9:22 am - 3:26 pmPNS-MDW
6h 04m1 stop
$229Delta
Find Deal
Sat, Nov 15 - Sat, Nov 22
American Airlines Logo
10:11 am - 12:41 pmORD-PNS
2h 30mnonstop
American Airlines Logo
1:17 pm - 3:55 pmPNS-ORD
2h 38mnonstop
$236American Airlines
Find Deal
Booking Insights

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 $217 and was between Chicago O'Hare Intl Airport (ORD) and Pensacola (PNS). On average, the best prices are found if you fly from Chicago Midway Airport (MDW) to Pensacola (PNS). The average price for a return flight for this route is $217.

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 $408 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $695 on average.

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, 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$79
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 12% 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 $160 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 A319 is the aircraft model that flies most regularly on the Chicago to Pensacola flight route.

  • Which airline alliances offer flights from Chicago to Pensacola?

    Star Alliance is the only airline alliance operating flights between Chicago and Pensacola.

  • 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 $381 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 $308 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 $186 or less one-way and $302 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

United Airlines

United Airlines

Wednesday

United Airlines

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

United Airlines

United Airlines

Wednesday

United Airlines

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 4246 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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!

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

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.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

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.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

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

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

I am very happy with my experience with Spirit Airlines. Both flights were on time. Boarding was very pleasant. Crew was very nice. Flights were amazing and we even arrived earlier than the schedule time. I am hoping Spirits keeps on having non stop flight from Ft Lauderdale to Hartford for many years to come.

you guys canceled my flight last minute and lost my luggage.

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.

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

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