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CHI - PNS

Find cheap flights from Chicago to Pensacola from $59

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 5/6. 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
Sun 5/19
Sun 5/26

Search 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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola.
In the last 7 days travelers have searched 44,212,662 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
5:30 am - 4:55 pmMDW-PNS
11h 25m1 stop
9:53 pm - 8:31 amPNS-MDW
10h 38m1 stop
$98Frontier
Find Deal
Tue, May 7 - Sat, May 11
10:53 pm - 5:27 pmMDW-PNS
18h 34m1 stop
9:53 pm - 8:31 amPNS-MDW
10h 38m1 stop
$100Frontier
Find Deal
Thu, May 9 - Sat, May 11
5:41 pm - 8:02 amORD-PNS
14h 21m1 stop
10:36 am - 11:10 pmPNS-ORD
12h 34m1 stop
$130Spirit Airlines
Find Deal
Sat, May 11 - Tue, May 14
5:00 am - 5:31 pmORD-PNS
12h 31m1 stop
6:21 pm - 9:55 amPNS-ORD
15h 34m1 stop
$135Spirit Airlines
Find Deal
Sat, May 18 - Tue, May 21
7:10 am - 12:49 pmORD-PNS
5h 39m1 stop
5:45 pm - 11:59 pmPNS-ORD
6h 14m1 stop
$208Delta
Find Deal
Tue, Sep 10 - Thu, Sep 19
12:42 pm - 6:27 pmMDW-PNS
5h 45m1 stop
5:57 pm - 10:01 pmPNS-MDW
4h 04m1 stop
$208Delta
Find Deal
Tue, May 14 - Wed, May 15
4:45 pm - 8:59 pmORD-PNS
4h 14m1 stop
6:22 pm - 11:55 pmPNS-ORD
5h 33m1 stop
$240American Airlines
Find Deal
Fri, Jul 26 - Mon, Jul 29
10:45 am - 1:07 pmORD-PNS
2h 22mnonstop
2:12 pm - 4:49 pmPNS-ORD
2h 37mnonstop
$259United Airlines
Find Deal
Tue, Sep 10 - Tue, Sep 17
8:05 am - 10:30 amORD-PNS
2h 25mnonstop
4:56 pm - 11:00 pmPNS-ORD
6h 04m1 stop
$263American Airlines
Find Deal
Sat, May 18 - Sat, May 25
10:45 am - 1:07 pmORD-PNS
2h 22mnonstop
7:00 am - 12:52 pmPNS-ORD
5h 52m1 stop
$268United Airlines
Find Deal
Tue, Sep 10 - Sat, Sep 14

Flights from Chicago to Pensacola - Travel Insights & Trends

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.

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 one-way flights from Chicago to Pensacola.
Our data shows that the cheapest route for a one-way flight from Chicago to Pensacola cost $138 and was between Chicago O'Hare Intl Airport and Pensacola. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $237.

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

The average price of all flights from Chicago to Pensacola clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Pensacola on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to Pensacola. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

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 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 $340 on average. On the other hand, the most expensive months are March and April, where the average cost of tickets is $506 and $489 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Chicago to Pensacola, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 24 days before departure.

Which airlines provide the cheapest flights from Chicago to Pensacola?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago to Pensacola were found on Frontier ($98) and Spirit Airlines ($130). Frontier proposed the cheapest one-way flight at $59.

Which airlines fly non-stop between Chicago and Pensacola?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Pensacola.
There are 3 airlines that fly nonstop from Chicago to Pensacola. They are: American Airlines, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $137 for a one-way flight. On average, the best prices for this route can be found at American Airlines.

How many flights are there between Chicago and Pensacola per day?

Each day, there are between 1 and 4 nonstop flights that take off from Chicago and land in Pensacola, with an average flight time of 2h 19m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 11 flights. The most frequent day of departure is Saturday, when 36% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between Chicago and Pensacola?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are First, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Pensacola take?

Direct flights take on average 2h 19m to travel the 788 miles between Chicago and Pensacola.

What’s the earliest departure time from Chicago to Pensacola?

Early birds can take the earliest flight from Chicago at 7:20 am and will be landing in Pensacola at 9:43 am.

What’s the latest departure time from Chicago to Pensacola?

If you prefer to fly at night, the latest flight from Chicago to Pensacola jets off at 11:08 am and lands at 1:30 pm.

Good to know

Low season

September

High season

March

Cheapest flight

$59
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 19% 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 $59 for a one-way ticket and $98 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 Boeing 737-800 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 oneworld 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, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Pensacola are Delta and United Airlines. With an average price for the route of $282 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $389 and an overall rating of 7.4.

  • 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.

See more FAQs

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 $182 or less one-way and $328 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.
See more tips

Prefer to fly non-stop from Chicago to Pensacola?

Find which airlines fly direct from Chicago to Pensacola, which days they fly and book direct flights.

Nonstop departures

Chicago to Pensacola

Monday

United Airlines, Southwest

United Airlines, Southwest

Tuesday

United Airlines, Southwest

United Airlines, Southwest

Wednesday

United Airlines, Southwest

United Airlines, Southwest

Thursday

United Airlines, Southwest

United Airlines, Southwest

Friday

United Airlines, Southwest

United Airlines, Southwest

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

Southwest, United Airlines

Southwest, United Airlines

See more direct flights

Nonstop returns

Pensacola to Chicago

Monday

Emirates, Lufthansa, United Airlines, +1 more

Emirates, Lufthansa, +2 more

Tuesday

Emirates, Lufthansa, United Airlines, +1 more

Emirates, Lufthansa, +2 more

Wednesday

Emirates, Lufthansa, United Airlines, +1 more

Emirates, Lufthansa, +2 more

Thursday

Emirates, Lufthansa, United Airlines, +1 more

Emirates, Lufthansa, +2 more

Friday

Emirates, Lufthansa, United Airlines, +1 more

Emirates, Lufthansa, +2 more

Saturday

American Airlines, Emirates, Lufthansa, +3 more

American Airlines, Emirates, +4 more

Sunday

Emirates, Lufthansa, Southwest, +1 more

Emirates, Lufthansa, +2 more

See more direct flights
See more direct flights

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
DeltaOverall score based on 11094 reviews
7.5food
8.2boarding
8.0entertainment
7.9comfort
8.6crew
Airline reviews

Seat back monitors and outlets were dead and not working.

8.0 ExcellentCarl, Apr 2024JFK - FLL
Read more about Delta reviews

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.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

Everything was smooth and easy to fly. No complains and a lot of thanks!

More space in the cabin. The guy in front of me leaned his seat back and I felt he was sitting in my lap.

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

The flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

No complaints. It’s a budget airline so can’t expect any frills.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

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.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

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.

The weight limit per bag was really low - 40 lbs - so we had to pay extra. Then, they said their carry on size was 14x18x8, and we measured our bag very carefully. It was within the limit, yet they said it was too big, so we ended up paying an extra $100 for that too!! So it wasn’t the cheap flight we thought it would be. Then, they moved up our initial flight to depart 3 hours earlier which meant we had to be out on the road by 7 am and then have a 6 hour layover and we got home at 2am. It was a grueling day. I won’t be flying with them again.

Overall it was a good experience. Stewards were very kind and professional. The departure and arrival times were as promised. Plane was clean.

Terrible as usual!!!! Very unprofessional and rude flight attendants! You get what you pay for! HORRIBLE

My experience was above excellent!!!! First the lady that pushed me in the wheelchair to the gate was outstanding!!! Then the ladies at the gate went over and beyond, by helping me fill out the immigration form! I would not have been able to get to Guatemala without their help!!! God bless them all! They were amazing 🙏❤️🙏

First....my trip was from Ft. Myers to Philly (not the other way around). Plane was clean, staff was friendly and flight was efficient with boarding and flight time. Thumbs up all around.

Early departure and arrival. Cabin very cold. Waited a while for luggage to come out

The no frills ticket price. The seats are very uncomfortable.

My flight experience was OK. The crew are friendly. The Flight was smooth. One thing that didn’t sit well with me was when I was checking in from RSW to head to Nashville the ticket agent told me I didn’t have a seat assignment and asked if I wanted to upgrade to first class for $50. I said no. I was placed in the third row middle seat. Upon taking off the flight attendant asked if anyone wanted to move. He specifically mentioned the third row was the worst because the lack of legroom. There were 70 open seats on the flight. Just wondering why with 70 open seats the ticket agent would place me in a middle seat in the worst row.

Flights are great except for the ticketing service on the terminal.. Too little employees taking care for lots of flights.

The airplane was extremely hot the air conditioner wasn’t working I

Book cheap flights from Chicago to Pensacola

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Pensacola found on KAYAK in the last 72 hours.
5/6Mon
1 stopFrontier
22h 28mORD-PNS
$59
5/4Sat
1 stopFrontier
10h 23mMDW-PNS
$60
5/10Fri
1 stopSpirit Airlines
22h 51mORD-PNS
$76
5/6Mon
2 stopsSpirit Airlines
11h 01mORD-PNS
$80
6/21Fri
1 stopAmerican Airlines
5h 23mORD-PNS
$103
6/17Mon
1 stopDelta
3h 49mORD-PNS
$104
4/29Mon
1 stopDelta
5h 31mORD-PNS
$139
6/23Sun
1 stopAmerican Airlines
6h 48mORD-PNS
$148
6/23Sun
nonstopUnited Airlines
2h 22mORD-PNS
$184
5/23Thu
nonstopUnited Airlines
2h 22mORD-PNS
$212

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Last minute flights from Chicago to Pensacola

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Pensacola that are departing in the next 10 days.
4/24Wed
multi-stopFrontier
23h 37mORD-PNS
4/27Sat
multi-stopFrontier
26h 38mPNS-ORD
$227
4/20Sat
multi-stopFrontier
11h 00mMDW-PNS
4/29Mon
multi-stopFrontier
14h 28mPNS-MDW
$258
4/23Tue
multi-stopSpirit Airlines
6h 09mORD-PNS
4/30Tue
multi-stopSpirit Airlines
6h 55mPNS-ORD
$286
4/20Sat
nonstopAmerican Airlines
2h 29mORD-PNS
4/27Sat
multi-stopAmerican Airlines
5h 01mPNS-ORD
$317
4/20Sat
nonstopAmerican Airlines
2h 29mORD-PNS
4/29Mon
multi-stopAmerican Airlines
5h 40mPNS-ORD
$318
4/24Wed
multi-stopDelta
6h 46mMDW-PNS
4/27Sat
multi-stopDelta
5h 25mPNS-MDW
$328
4/23Tue
multi-stopSpirit Airlines
6h 09mORD-PNS
4/24Wed
multi-stopSpirit Airlines
8h 38mPNS-ORD
$344
4/24Wed
nonstopUnited Airlines
2h 22mORD-PNS
4/27Sat
multi-stopUnited Airlines
8h 03mPNS-ORD
$388
4/20Sat
nonstopUnited Airlines
2h 22mORD-PNS
4/22Mon
nonstopUnited Airlines
2h 37mPNS-ORD
$409
4/23Tue
multi-stopDelta
4h 04mMDW-PNS
4/30Tue
multi-stopDelta
7h 30mPNS-MDW
$742

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Flights to Pensacola

Destination:

Pensacola (PNS)United States

Return flight deals:

Pensacola - Chicago

Cabin classes:

$980
$758
$480
$237