$81 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 4/2. 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
$250
Multiple Airlines
Fri 4/24Fri 5/1
MDW - PNS • 1 stop
Cheapest non-stop
$259
Typical prices: $288-$368
United Airlines
Fri 6/26Mon 6/29
ORD - 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

Fri, Apr 24 - Fri, May 1
Multiple Airlines Logo
6:49 pm - 9:38 pm
MDW
-
PNS
26h 49m
1 stop
Multiple Airlines Logo
6:36 am - 7:31 pm
PNS
-
MDW
12h 55m
2 stops
$250Multiple Airlines
Thu, Apr 16 - Thu, Apr 16
Multiple Airlines Logo
6:40 am - 3:36 pm
ORD
-
PNS
8h 56m
1 stop
Multiple Airlines Logo
7:24 pm - 9:50 am
PNS
-
ORD
14h 26m
1 stop
$251Multiple Airlines
Sat, Apr 4 - Sat, Apr 11
Spirit Airlines Logo
7:17 am - 1:16 pm
ORD
-
PNS
5h 59m
1 stop
Spirit Airlines Logo
2:15 pm - 7:51 pm
PNS
-
ORD
5h 36m
1 stop
$252Spirit Airlines
Thu, May 28 - Sun, May 31
Spirit Airlines Logo
6:40 am - 3:36 pm
ORD
-
PNS
8h 56m
1 stop
Spirit Airlines Logo
8:18 pm - 9:31 am
PNS
-
ORD
13h 13m
1 stop
$253Spirit Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
2:15 pm - 8:55 am
MDW
-
PNS
18h 40m
2 stops
Multiple Airlines Logo
4:31 pm - 8:04 am
PNS
-
MDW
15h 33m
1 stop
$253Multiple Airlines
Sun, Apr 12 - Mon, Apr 20
Spirit Airlines Logo
12:45 pm - 9:14 pm
ORD
-
PNS
8h 29m
1 stop
Spirit Airlines Logo
9:18 pm - 9:36 am
PNS
-
ORD
12h 18m
1 stop
$254Spirit Airlines
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
4:21 pm - 8:55 am
ORD
-
PNS
16h 34m
1 stop
Multiple Airlines Logo
3:36 pm - 6:30 pm
PNS
-
ORD
26h 54m
2 stops
$255Multiple Airlines
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
9:15 am - 2:20 pm
MDW
-
PNS
5h 05m
1 stop
Southwest Logo
2:50 pm - 5:10 pm
PNS
-
MDW
2h 20mnonstop
$257Southwest
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
10:00 am - 4:15 pm
MDW
-
PNS
6h 15m
2 stops
Southwest Logo
2:50 pm - 5:10 pm
PNS
-
MDW
2h 20mnonstop
$262Southwest
Fri, May 29 - Sun, May 31
Delta Logo
12:51 pm - 6:23 pm
MDW
-
PNS
5h 32m
1 stop
Delta Logo
6:00 am - 10:00 am
PNS
-
MDW
4h 00m
1 stop
$267Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$81
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 20% 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?

    8 direct flights run between Chicago and Gulf Shores on a daily basis. On average, there are about 61 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 Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays 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 72 hours, the cheapest one-way ticket between Chicago and Gulf Shores found on KAYAK was with Spirit Airlines for $73. Delta offered a round-trip connection from $113 and Spirit Airlines from $126.

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 February, March and April. The cheapest month to fly is September.

Reviews of the 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 4318 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The plane was clean and crew was nice. Can’t speak on food as I did not have any

Flight was delayed, then undelayed, then delayed again. Gate was changed to the other side of the airport. Horrible seats with no screens. Spirit os truly awful, even for a budget option.

flight delayed because of poor staffing and organization - confusion from gate agents and flight attendant supervisors scheduling a missing flight attendant. flight delay 1 hr 30 min

I liked the quickness of the boarding process. Things were run smoothly and the staff was very professional. The overall experience was great.

Flight was delayed more than 3 hours, and the metro had stopped running by the time we got to the terminal well past midnight, so I was stranded, alone, with no way to get home until the metro started up the next morning.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

When I arrived at the airport at 4:00 in the morning, I was notified that I "hadn't paid" for my ticket (I had paid and had a boarding pass). Then I was told that while I had paid, the ticket was $600 more than it actually was, and that I needed to pay that so I could board. None of this was true, of course, but it took 20 minutes, two crew members behind the desk, and one on the phone to clear up.

The flight was delayed by two hours, then by three hours. Then, at 10:01, a notification that the flight was back on schedule for the original time. I just happened to be getting on a train to go to the airport at 10 just to be extra early for the delayed departure when I saw the update come through. I got to the train terminal at the airport at 11:07. A shuttle immediately arrived and offloaded, but didn't show anyone on before speeding off. It was 30 minutes before another arrived. I finally got to the terminal and through security and to the gate just in time for them to tell me the door had just been locked. Flight closed. I had to wait until the next day to fly out. No or for a hotel, a meal, nothing.

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Everything you need to know for your flight from Chicago to Gulf Shores

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