$79 Find Cheap Flights from Chicago to Gulf Shores

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 7/8. 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.
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1 adult, Economy

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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

Tue, Jul 8 - Tue, Jul 15
Spirit Airlines Logo
10:46 am - 10:37 pmORD-PNS
11h 51m1 stop
Spirit Airlines Logo
6:00 am - 3:31 pmPNS-ORD
9h 31m1 stop
$171Spirit Airlines
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Tue, Jul 8 - Wed, Jul 23
Spirit Airlines Logo
10:46 am - 10:37 pmORD-PNS
11h 51m1 stop
Spirit Airlines Logo
6:00 am - 3:31 pmPNS-ORD
9h 31m1 stop
$173Spirit Airlines
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Tue, Aug 5 - Wed, Aug 13
Delta Logo
1:35 pm - 7:07 pmORD-PNS
5h 32m1 stop
Delta Logo
6:00 am - 10:04 amPNS-ORD
4h 04m1 stop
$177Delta
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Mon, Sep 29 - Wed, Oct 8
Delta Logo
6:00 am - 10:46 amMDW-PNS
4h 46m1 stop
Delta Logo
6:00 am - 9:51 amPNS-MDW
3h 51m1 stop
$177Delta
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Sat, Sep 6 - Mon, Sep 8
Southwest Logo
8:20 am - 10:30 amMDW-PNS
2h 10mnonstop
Southwest Logo
4:35 pm - 10:50 pmPNS-MDW
6h 15m1 stop
$224Southwest
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Tue, Aug 5 - Thu, Aug 7
United Airlines Logo
10:39 am - 1:06 pmORD-PNS
2h 27mnonstop
United Airlines Logo
2:08 pm - 4:47 pmPNS-ORD
2h 39mnonstop
$227United Airlines
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Mon, Aug 11 - Fri, Aug 15
Southwest Logo
6:30 am - 10:20 amMDW-PNS
3h 50m1 stop
Southwest Logo
4:35 pm - 8:35 pmPNS-MDW
4h 00m1 stop
$237Southwest
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Thu, Oct 16 - Mon, Oct 27
American Airlines Logo
5:00 am - 12:14 pmORD-PNS
7h 14m1 stop
American Airlines Logo
7:40 pm - 12:59 amPNS-ORD
5h 19m1 stop
$251American Airlines
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Wed, Jul 16 - Sun, Jul 20
United Airlines Logo
10:39 am - 1:06 pmORD-PNS
2h 27mnonstop
United Airlines Logo
2:08 pm - 4:47 pmPNS-ORD
2h 39mnonstop
$277United Airlines
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Sun, Aug 3 - Sat, Aug 9
American Airlines Logo
8:23 am - 10:39 amORD-PNS
2h 16mnonstop
American Airlines Logo
7:10 am - 12:22 pmPNS-ORD
5h 12m1 stop
$285American Airlines
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Good to know

Low seasonJanuary
High seasonMarch
Cheapest flight$79
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 8% 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 05m.

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

    3 direct flights run between Chicago and Gulf Shores on a daily basis. On average, there are about 23 departures each week.

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

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

  • 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 72 hours, the cheapest one-way ticket between Chicago and Gulf Shores found on KAYAK was with Spirit Airlines for $79. Spirit Airlines offered a round-trip connection from $171 and Delta from $177.

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 84 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 November, December and January. The cheapest month to fly is January.

Top 5 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.
8.0
SouthwestOverall score based on 4287 reviews
7.1Food
7.6Entertainment
8.2Boarding
8.0Comfort
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

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.

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

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

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.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

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