$111 Find Cheap Flights from Chicago to Gulf Shores - Compare and Save

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 Gulf Shores departing on 9/14. 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

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Everything you should know

Cheapest round-trip
$361
Typical prices: $386-$287
Southwest
Mon 8/10Thu 8/13
MDW - PNS • 1 stop
Cheapest non-stop
$376
Southwest
Tue 7/21Sat 7/25
MDW - PNS • Non-stop
Arrival airport
You can't fly directly to Gulf Shores. It is served by Pensacola (PNS), located 34.4 miles from Gulf Shores.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Gulf Shores (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 Gulf Shores 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 Gulf Shores

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
Tue, Aug 4 - Sat, Aug 15
Multiple Airlines Logo
9:34 pm - 1:21 pm
ORD
-
PNS
15h 47m
2 stops
Multiple Airlines Logo
8:26 am - 11:10 pm
PNS
-
ORD
14h 44m
1 stop
$361Multiple Airlines
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
Fri, Jul 3 - Wed, Jul 8
Multiple Airlines Logo
12:10 pm - 10:30 am
ORD
-
PNS
22h 20m
1 stop
Multiple Airlines Logo
4:29 pm - 11:10 pm
PNS
-
ORD
6h 41m
1 stop
$363Multiple Airlines
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
6:05 am - 4:33 pm
ORD
-
PNS
10h 28m
1 stop
Frontier Logo
5:30 pm - 1:16 pm
PNS
-
ORD
19h 46m
1 stop
$364Frontier
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
Mon, Aug 10 - Sat, Aug 15
American Airlines Logo
11:59 am - 2:23 pm
ORD
-
PNS
2h 24mnonstop
American Airlines Logo
1:56 pm - 7:46 pm
PNS
-
ORD
5h 50m
1 stop
$366American Airlines
Mon, Aug 17 - Tue, Aug 25
Delta Logo
6:05 am - 10:43 am
MDW
-
PNS
4h 38m
1 stop
Delta Logo
11:51 am - 4:15 pm
PNS
-
MDW
4h 24m
1 stop
$366Delta
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
Sat, Aug 1 - Sat, Aug 8
Delta Logo
6:00 am - 10:46 am
MDW
-
PNS
4h 46m
1 stop
Delta Logo
9:22 am - 3:38 pm
PNS
-
MDW
6h 16m
1 stop
$375Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$111
Best time to beat the crowds with an average 4% 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 Gulf Shores

Are your dates flexible? Find out the best times to travel from Chicago to Gulf Shores 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 Gulf Shores

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

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Gulf Shores does not have its own airport so you’ll be flying into nearby Pensacola airport, which is 34.4 mi away.

  • How long does a flight from Chicago to Gulf Shores take?

    Direct flights cover the 788 miles separating Chicago and Gulf Shores in about 2h 10m.

  • How many flights are there between Chicago and Gulf Shores?

    5 direct flights run between Chicago and Gulf Shores on a daily basis. On average, there are about 36 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Gulf Shores?

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

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

    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 Gulf Shores.

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

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

    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 Gulf Shores 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 Gulf Shores?

    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 Gulf Shores 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 Gulf Shores?

    In the last 5 days, the cheapest one-way ticket between Chicago and Gulf Shores found on KAYAK was with Delta for $88. Delta offered a round-trip connection from $128 and Southwest from $207.

Top tips for finding cheap flights from Chicago to Gulf Shores

  • There is no airport in Gulf Shores. Instead, you’ll be flying into Pensacola Airport when flying between Chicago and Gulf Shores.
  • The cheapest flight from Chicago to Gulf Shores was found 70 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 May, June and July. The cheapest month to fly is November.

Reviews of the top 4 airlines serving Chicago to Gulf Shores

 
Need help choosing which airline to fly with from Chicago to Gulf Shores? 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 4237 reviews
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

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.

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 Gulf Shores

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