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Find cheap flights from Chicago to Pensacola Beach from $40

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 Beach departing on 6/4. 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
0 bags
Thu 6/27
Thu 7/4

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Good to know

Low season

September

High season

March

Cheapest flight

$40
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago O'Hare Airport to Pensacola

When to book flights from Chicago to Pensacola Beach

Are your dates flexible? Find out the best times to travel from Chicago to Pensacola Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Pensacola Beach

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

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Pensacola Beach does not have its own airport so you’ll be flying into nearby Pensacola airport, which is 10.2 mi away.

  • How long does a flight from Chicago to Pensacola Beach take?

    Direct flights cover the 788 miles separating Chicago and Pensacola Beach in about 2h 22m.

  • How many flights are there between Chicago and Pensacola Beach?

    2 direct flights run between Chicago and Pensacola Beach on a daily basis. On average, there are about 18 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Pensacola Beach?

    Consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Sundays.

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

    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 Beach.

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

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

    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 Beach 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 Beach?

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

  • Which airlines provide the cheapest flights from Chicago to Pensacola Beach?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Pensacola Beach found on KAYAK was with Spirit Airlines for $40. Frontier offered a round-trip connection from $159 and Delta from $208.

See more FAQs

Top tips for finding cheap flights from Chicago to Pensacola Beach

  • There is no airport in Pensacola Beach. Instead, you’ll be flying into Pensacola Airport when flying between Chicago and Pensacola Beach.
  • The cheapest flight from Chicago to Pensacola Beach was found 63 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is January.
See more tips

Top 5 airlines serving Chicago to Pensacola Beach

 
Need help choosing which airline to fly with from Chicago to Pensacola Beach? 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
DeltaOverall score based on 10502 reviews
7.9Comfort
8.6Crew
8.2Boarding
7.4Food
8.0Entertainment
Airline reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

2.0 MediocreNairan, May 2024JFK - FLL
Read more about Delta reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

Everything was really good but the seats are not very comfortable.

Spirit canceled the flight in March and never notified me!

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

There was no wifi, there was no usb charger on the planes Frontier lowered the weight limit on suitcases from 50 to 40 pounds Frontier now charges for a seat...really? If i don't pay for a basic seat, do i stand the whole flight? Frontier now charges for the carry on, just like for the checked suitcase The bundle pricing is way over priced.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Book cheap flights from Chicago to Pensacola Beach

Recent round-trip flight deals

8/20Tue
1 stopFrontier
10h 49mMDW-PNS
8/24Sat
1 stopFrontier
15h 42mPNS-MDW
$159
8/19Mon
1 stopFrontier
13h 13mMDW-PNS
8/24Sat
1 stopFrontier
15h 42mPNS-MDW
$176
7/5Fri
1 stopDelta
4h 22mMDW-PNS
7/10Wed
1 stopDelta
4h 03mPNS-MDW
$208
7/8Mon
1 stopSpirit Airlines
23h 41mORD-PNS
7/18Thu
1 stopSpirit Airlines
12h 29mPNS-ORD
$208
6/8Sat
1 stopSpirit Airlines
12h 31mORD-PNS
6/12Wed
3 stopsSpirit Airlines
24h 24mPNS-ORD
$209
7/4Thu
1 stopDelta
4h 47mORD-PNS
7/9Tue
1 stopDelta
7h 09mPNS-ORD
$243
6/1Sat
nonstopAmerican Airlines
2h 25mORD-PNS
6/8Sat
1 stopAmerican Airlines
6h 59mPNS-ORD
$317
6/25Tue
nonstopUnited Airlines
2h 22mORD-PNS
7/2Tue
nonstopUnited Airlines
2h 37mPNS-ORD
$338
7/6Sat
1 stopAmerican Airlines
4h 42mORD-PNS
7/13Sat
1 stopAmerican Airlines
5h 32mPNS-ORD
$345
6/25Tue
nonstopUnited Airlines
2h 22mORD-PNS
7/2Tue
1 stopUnited Airlines
7h 43mPNS-ORD
$348

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Recent one-way flight deals

6/4Tue
1 stopSpirit Airlines
14h 35mORD-PNS
$40
7/16Tue
1 stopSpirit Airlines
12h 30mORD-PNS
$58
6/4Tue
1 stopFrontier
10h 55mMDW-PNS
$96
9/5Thu
1 stopFrontier
13h 13mMDW-PNS
$102
6/6Thu
1 stopAmerican Airlines
6h 07mORD-PNS
$173
7/14Sun
1 stopDelta
4h 20mMDW-PNS
$179
6/19Wed
nonstopUnited Airlines
2h 22mORD-PNS
$185
7/19Fri
nonstopUnited Airlines
2h 22mORD-PNS
$189
6/17Mon
2 stopsAmerican Airlines
6h 37mORD-PNS
$500
6/24Mon
2 stopsDelta
8h 04mMDW-PNS
$516

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Last minute flights from Chicago to Pensacola Beach

Last minute flight, train and bus deals

6/1Sat
multi-stop
21h 23mORD-PNS
6/5Wed
multi-stop
15h 45mPNS-ORD
$238
6/1Sat
multi-stopFrontier
17h 18mMDW-PNS
6/8Sat
multi-stopFrontier
16h 48mPNS-MDW
$258
5/31Fri
multi-stopSpirit Airlines
25h 52mORD-PNS
6/4Tue
multi-stopSpirit Airlines
21h 46mPNS-ORD
$273
5/29Wed
multi-stopSpirit Airlines
24h 20mORD-PNS
6/5Wed
multi-stopSpirit Airlines
15h 45mPNS-ORD
$281
6/1Sat
nonstopAmerican Airlines
2h 25mORD-PNS
6/8Sat
multi-stopAmerican Airlines
5h 49mPNS-ORD
$317
6/1Sat
multi-stopAmerican Airlines
4h 24mORD-PNS
6/8Sat
multi-stopAmerican Airlines
6h 58mPNS-ORD
$325
5/31Fri
multi-stopDelta
5h 44mORD-PNS
6/1Sat
multi-stopDelta
6h 03mPNS-ORD
$378
5/30Thu
multi-stopDelta
4h 54mMDW-PNS
6/2Sun
multi-stopDelta
4h 04mPNS-MDW
$378
5/31Fri
nonstopUnited Airlines
2h 22mORD-PNS
6/4Tue
multi-stopUnited Airlines
17h 13mPNS-ORD
$588
5/30Thu
nonstopUnited Airlines
2h 22mORD-PNS
6/2Sun
multi-stopUnited Airlines
24h 41mPNS-ORD
$709

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Flights to Pensacola Beach