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Find cheap flights from Chicago to Gulf Shores from $68

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 6/26. 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
Sat 7/6
Sat 7/13

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Good to know

Low season

September

High season

March

Cheapest flight

$68
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 4h 19m.

  • 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 Tuesday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays 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 $68. Spirit Airlines offered a round-trip connection from $125 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 10371 reviews
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
8.6Crew
Airline reviews

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

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

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!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

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

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.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

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.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Book cheap flights from Chicago to Gulf Shores

Recent round-trip flight deals

6/25Tue
1 stopSpirit Airlines
11h 54mORD-PNS
7/4Thu
1 stopSpirit Airlines
6h 19mPNS-ORD
$125
6/25Tue
1 stopSpirit Airlines
5h 39mORD-PNS
7/1Mon
1 stopSpirit Airlines
6h 29mPNS-ORD
$131
9/11Wed
2 stopsSpirit Airlines
20h 47mORD-PNS
9/17Tue
1 stopSpirit Airlines
8h 00mPNS-ORD
$134
9/11Wed
1 stopFrontier
13h 13mMDW-PNS
9/17Tue
1 stopFrontier
15h 42mPNS-MDW
$148
8/19Mon
1 stopFrontier
13h 13mMDW-PNS
8/24Sat
1 stopFrontier
15h 42mPNS-MDW
$185
10/19Sat
1 stopDelta
7h 06mORD-PNS
10/26Sat
1 stopDelta
6h 44mPNS-ORD
$208
6/25Tue
1 stopDelta
7h 00mMDW-PNS
7/1Mon
1 stopDelta
4h 55mPNS-MDW
$208
6/15Sat
1 stop
12h 31mORD-PNS
6/21Fri
1 stop
23h 15mPNS-ORD
$256
6/15Sat
1 stop
12h 31mORD-PNS
6/19Wed
1 stop
27h 14mPNS-ORD
$276
7/16Tue
nonstopUnited Airlines
2h 22mORD-PNS
7/23Tue
nonstopUnited Airlines
2h 37mPNS-ORD
$299

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Recent one-way flight deals

6/26Wed
1 stopSpirit Airlines
25h 57mORD-PNS
$68
6/25Tue
1 stopSpirit Airlines
5h 39mORD-PNS
$73
8/9Fri
1 stopFrontier
10h 59mMDW-PNS
$103
8/9Fri
1 stopDelta
4h 56mORD-PNS
$114
6/25Tue
1 stopDelta
4h 23mMDW-PNS
$114
6/12Wed
1 stopAmerican Airlines
7h 41mORD-PNS
$139
6/12Wed
1 stopFrontier
14h 29mMDW-PNS
$163
8/3Sat
nonstopAmerican Airlines
2h 29mORD-PNS
$170
7/22Mon
1 stopUnited Airlines
20h 55mORD-PNS
$188
7/25Thu
nonstopUnited Airlines
2h 22mORD-PNS
$189

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Last minute flights from Chicago to Gulf Shores

Last minute flight, train and bus deals

6/8Sat
multi-stopFrontier
11h 44mMDW-PNS
6/19Wed
multi-stopFrontier
5h 44mPNS-MDW
$199
6/8Sat
multi-stopFrontier
11h 44mMDW-PNS
6/17Mon
multi-stopFrontier
5h 50mPNS-MDW
$204
6/10Mon
multi-stopSpirit Airlines
13h 15mORD-PNS
6/18Tue
multi-stopSpirit Airlines
16h 12mPNS-ORD
$326
6/8Sat
multi-stopDelta
5h 46mORD-PNS
6/12Wed
multi-stopDelta
6h 14mPNS-ORD
$328
6/10Mon
multi-stopSpirit Airlines
13h 15mORD-PNS
6/20Thu
multi-stopSpirit Airlines
22h 21mPNS-ORD
$339
6/7Fri
multi-stopDelta
5h 46mORD-PNS
6/8Sat
multi-stopDelta
4h 46mPNS-ORD
$378
6/9Sun
multi-stopAmerican Airlines
5h 08mORD-PNS
6/13Thu
multi-stopAmerican Airlines
8h 23mPNS-ORD
$398
6/7Fri
multi-stopAmerican Airlines
4h 42mORD-PNS
6/9Sun
multi-stopAmerican Airlines
4h 40mPNS-ORD
$448
6/9Sun
nonstopUnited Airlines
2h 22mORD-PNS
6/13Thu
multi-stopUnited Airlines
18h 08mPNS-ORD
$732
6/9Sun
nonstopUnited Airlines
2h 22mORD-PNS
6/14Fri
nonstopUnited Airlines
2h 36mPNS-ORD
$733

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Flights to Gulf Shores