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Find cheap flights from Chicago to Gulf Shores from $73

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 6/25. 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
Wed 7/10
Wed 7/17

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Good to know

Low season

September

High season

March

Cheapest flight

$73
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 24% 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 22m.

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

    2 direct flights run between Chicago and Gulf Shores on a daily basis. On average, there are about 18 departures each week.

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

    Consider leaving on a Sunday and avoid Saturdays 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 Thursdays.

  • 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. Spirit Airlines offered a round-trip connection from $128 and Frontier from $148.

See more FAQs

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 63 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 January.
See more tips

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
DeltaOverall score based on 10295 reviews
7.9Comfort
8.2Boarding
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Book cheap flights from Chicago to Gulf Shores

Recent round-trip flight deals

9/8Sun
1 stopSpirit Airlines
14h 25mORD-PNS
9/11Wed
1 stopSpirit Airlines
7h 11mPNS-ORD
$128
7/9Tue
1 stopSpirit Airlines
11h 54mORD-PNS
7/11Thu
1 stopSpirit Airlines
11h 00mPNS-ORD
$137
7/17Wed
1 stopFrontier
14h 12mMDW-PNS
7/22Mon
1 stopFrontier
23h 36mPNS-MDW
$148
8/22Thu
1 stopFrontier
13h 13mMDW-PNS
8/26Mon
1 stopFrontier
15h 42mPNS-MDW
$150
10/19Sat
1 stopDelta
5h 10mORD-PNS
10/23Wed
1 stopDelta
4h 50mPNS-ORD
$208
10/19Sat
1 stopDelta
4h 42mMDW-PNS
10/26Sat
1 stopDelta
6h 26mPNS-MDW
$208
9/4Wed
1 stopAmerican Airlines
5h 49mORD-PNS
9/4Wed
1 stopAmerican Airlines
7h 34mPNS-ORD
$297
7/16Tue
nonstopUnited Airlines
2h 22mORD-PNS
7/23Tue
nonstopUnited Airlines
2h 37mPNS-ORD
$299
7/16Tue
nonstopUnited Airlines
2h 22mORD-PNS
7/23Tue
1 stopUnited Airlines
6h 50mPNS-ORD
$309
7/20Sat
nonstopAmerican Airlines
2h 29mORD-PNS
7/27Sat
nonstopAmerican Airlines
2h 32mPNS-ORD
$360

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Recent one-way flight deals

6/25Tue
1 stopSpirit Airlines
5h 39mORD-PNS
$73
6/26Wed
1 stopSpirit Airlines
15h 33mORD-PNS
$81
7/15Mon
1 stopFrontier
14h 34mMDW-PNS
$82
7/18Thu
1 stopDelta
5h 47mORD-PNS
$104
8/22Thu
1 stopDelta
5h 12mMDW-PNS
$104
7/18Thu
1 stopFrontier
21h 52mMDW-PNS
$105
7/22Mon
1 stopAmerican Airlines
5h 29mORD-PNS
$184
7/20Sat
2 stopsAmerican Airlines
8h 53mORD-PNS
$189
8/29Thu
nonstopUnited Airlines
2h 22mORD-PNS
$222
7/18Thu
nonstopUnited Airlines
2h 22mORD-PNS
$224

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Last minute flights from Chicago to Gulf Shores

Last minute flight, train and bus deals

6/11Tue
multi-stopFrontier
8h 32mMDW-PNS
6/14Fri
multi-stopFrontier
5h 51mPNS-MDW
$198
6/13Thu
multi-stopFrontier
22h 08mMDW-PNS
6/15Sat
multi-stopFrontier
16h 48mPNS-MDW
$203
6/12Wed
multi-stopSpirit Airlines
11h 54mORD-PNS
6/19Wed
multi-stopSpirit Airlines
8h 34mPNS-ORD
$335
6/13Thu
multi-stopSpirit Airlines
9h 24mORD-PNS
6/17Mon
multi-stopSpirit Airlines
6h 29mPNS-ORD
$361
6/13Thu
nonstopUnited Airlines
2h 22mORD-PNS
6/17Mon
multi-stopUnited Airlines
18h 08mPNS-ORD
$642
6/13Thu
multi-stopAmerican Airlines
6h 06mORD-PNS
6/15Sat
nonstopAmerican Airlines
2h 29mPNS-ORD
$674
6/12Wed
nonstopUnited Airlines
2h 22mORD-PNS
6/19Wed
nonstopUnited Airlines
2h 36mPNS-ORD
$733
6/13Thu
multi-stopAmerican Airlines
7h 00mORD-PNS
6/17Mon
multi-stopAmerican Airlines
6h 56mPNS-ORD
$855
6/14Fri
multi-stopDelta
10h 17mMDW-PNS
6/15Sat
multi-stopDelta
5h 55mPNS-MDW
$1,038
6/13Thu
multi-stopDelta
8h 49mMDW-PNS
6/17Mon
multi-stopDelta
4h 06mPNS-MDW
$1,113

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Flights to Gulf Shores