CHI - PNS

$113 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 9/8. 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, 0 bags

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
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Everything you should know

Cheapest round-trip
$361
Typical prices: $584-$299
Multiple Airlines
Tue 8/4Wed 8/12
ORD - PNS • 1 stop
Cheapest non-stop
$376
Southwest
Tue 7/21Sat 7/25
MDW - PNS • Non-stop
Top airlines
Cheapest • from $361 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 18m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 12% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 55% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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We hope you love your trip to Pensacola!
Flight Deals
Booking Insights
Expert advice
Flight 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, Aug 4 - Wed, Aug 12
Multiple Airlines Logo
5:13 pm - 12:09 pm
ORD
-
PNS
18h 56m
1 stop
Multiple Airlines Logo
8:26 am - 7:53 pm
PNS
-
ORD
11h 27m
2 stops
$361Multiple Airlines
Mon, Aug 10 - Thu, Aug 13
Southwest Logo
5:55 am - 9:30 am
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
7:45 am - 3:30 pm
PNS
-
MDW
7h 45m
2 stops
$361Southwest
Mon, Aug 3 - Tue, Aug 11
Multiple Airlines Logo
8:05 am - 6:52 pm
ORD
-
PNS
10h 47m
1 stop
Multiple Airlines Logo
2:07 pm - 5:37 am
PNS
-
ORD
15h 30m
2 stops
$362Multiple Airlines
Sun, Sep 13 - Wed, Sep 16
Southwest Logo
1:15 pm - 8:15 pm
MDW
-
PNS
7h 00m
2 stops
Southwest Logo
3:00 pm - 11:10 pm
PNS
-
MDW
8h 10m
2 stops
$362Southwest
Sat, Aug 1 - Sat, Aug 8
American Airlines Logo
10:05 am - 5:06 pm
ORD
-
PNS
7h 01m
1 stop
American Airlines Logo
2:59 pm - 5:49 pm
PNS
-
ORD
2h 50mnonstop
$365American Airlines
Tue, Aug 4 - Mon, Aug 10
Delta Logo
5:30 am - 10:43 am
ORD
-
PNS
5h 13m
1 stop
Delta Logo
7:00 am - 2:09 pm
PNS
-
ORD
7h 09m
1 stop
$366Delta
Mon, Aug 17 - Wed, Aug 26
Delta Logo
6:05 am - 10:43 am
MDW
-
PNS
4h 38m
1 stop
Delta Logo
5:00 pm - 10:36 pm
PNS
-
MDW
5h 36m
1 stop
$366Delta
Thu, Nov 5 - Mon, Nov 9
American Airlines Logo
2:50 pm - 10:55 pm
ORD
-
PNS
8h 05m
1 stop
American Airlines Logo
1:17 pm - 3:55 pm
PNS
-
ORD
2h 38mnonstop
$367American Airlines
Sun, Sep 13 - Fri, Sep 18
Frontier Logo
4:49 pm - 4:33 pm
ORD
-
PNS
23h 44m
1 stop
Frontier Logo
6:59 pm - 9:35 pm
PNS
-
ORD
26h 36m
1 stop
$368Frontier
Mon, Jul 6 - Mon, Jul 13
Frontier Logo
5:13 pm - 3:46 pm
ORD
-
PNS
22h 33m
1 stop
Frontier Logo
4:11 pm - 11:10 pm
PNS
-
ORD
6h 59m
1 stop
$369Frontier
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.

How much is a round-trip flight from Chicago to Pensacola?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Pensacola departing in August.

What is the cheapest Chicago to Pensacola flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Chicago to Pensacola costs $357 on the route between Chicago O'Hare Intl Airport (ORD) and Pensacola (PNS). However, over the past month, flights between Chicago Midway Airport (MDW) and Pensacola (PNS) were, on average, 1% cheaper than other Chicago-Pensacola routes. The most popular route is between Chicago O'Hare Intl Airport (ORD) and Pensacola (PNS).

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, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Pensacola back to Chicago, the best deals are generally found on Friday, with Sunday 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 October, where tickets cost $76 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $584 and $207 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 2 stops layover the cheapest option at $349 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 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Pensacola

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonJanuary
Cheapest flight$113
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 9% 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 5 days, the lowest price for a flight from Chicago to Pensacola was $111 for a one-way ticket and $361 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?

    American Airlines, Alaska Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago to Pensacola flight route.

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

    The Embraer 175 is the aircraft model that flies most regularly on the Chicago to Pensacola flight route.

  • Which airline alliances offer flights from Chicago to Pensacola?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Pensacola, with SkyTeam 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 $374 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $295 and an overall rating of 7.9.

  • 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 $183 or less one-way and $403 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

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

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

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

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 4 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.
7.9
SouthwestOverall score based on 4235 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Very easy to use and convenient, you can perform any action within the same portal

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Okay considering we had weather delays which the Pilot notified us of immediately!

N Everything was perfect from boarding to assistance to baggage in Tampa

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

Information on your arrival and departure airports