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Gulf Shores

$79+ Cheap flights from Chicago (CHI) to Gulf Shores, AL

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Gulf Shores are usually found in January or April, booked 84 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Gulf Shores

Keep the following information in mind while searching for Chicago to Gulf Shores flight deals. Data was last updated julio 31, 2025.

Round-trip from

$240
(United Airlines)

One-way from

$79
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$376
From Chicago (CHI) to Gulf Shores
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One-way flight from Chicago (CHI) to Gulf Shores
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chicago to Gulf Shores

Cheapest flights from Chicago to Gulf Shores
Explore the most affordable flight options available from Chicago to Gulf Shores. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/2510:50 amORD - PNS
Nonstop2h 25mUnited Airlines
mar. 9/302:17 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Deal found 7/29$240
This Mytrip deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/138:12 pmORD - PNS
2 stops20h 55mSpirit Airlines
sáb. 8/169:14 amPNS - ORD
1 stop9h 53mSpirit Airlines
Deal found 7/30$241
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/187:50 amMDW - PNS
1 stop6h 45mSouthwest
lun. 9/2210:00 amPNS - MDW
2 stops7h 45mSouthwest
Deal found 7/31$242
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/233:10 pmORD - PNS
1 stop3h 45mSouthwest
mar. 9/307:35 amPNS - ORD
2 stops10h 20mSouthwest
Deal found 7/30$242
This FlightHub deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/124:48 pmMDW - PNS
1 stop23h 38mFrontier
dom. 9/145:21 pmPNS - MDW
1 stop22h 32mFrontier
Deal found 7/30$245
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/510:30 amORD - PNS
Nonstop2h 30mAmerican Airlines
mar. 11/116:00 amPNS - ORD
1 stop6h 07mAmerican Airlines
Deal found 7/31$246
This CheapOair deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/27:00 amORD - PNS
1 stop8h 34mMultiple Airlines
sáb. 8/96:00 amPNS - ORD
1 stop10h 57mMultiple Airlines
Deal found 7/29$253
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/116:00 amMDW - PNS
1 stop4h 50mDelta
mié. 9/175:00 pmPNS - MDW
1 stop4h 36mDelta
Deal found 7/30$260
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/155:30 amORD - PNS
1 stop5h 20mDelta
sáb. 9/206:00 amPNS - ORD
1 stop4h 10mDelta
Deal found 7/30$260
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/126:00 amORD - PNS
1 stop10h 26mFrontier
dom. 9/145:21 pmPNS - ORD
1 stop6h 38mFrontier
Deal found 7/30$268

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Gulf Shores that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 31, 2025.
Use the filters below to find and compare flights from Chicago to Gulf Shores that are best for you.

Fly from

Chicago

Fly to

Gulf Shores

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

jue. 9/25

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

mar. 9/30

2:17 pm-4:54 pm

Nonstop2h 37m

$240

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mié. 8/13

8:12 pm-5:07 pm

2 stops20h 55m

Pensacola

sáb. 8/16

9:14 am-7:07 pm

1 stop9h 53m

$241

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

jue. 9/18

7:50 am-2:35 pm

1 stop6h 45m

Pensacola

lun. 9/22

10:00 am-5:45 pm

2 stops7h 45m

$242

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 9/23

3:10 pm-6:55 pm

1 stop3h 45m

Pensacola

mar. 9/30

7:35 am-5:55 pm

2 stops10h 20m

$242

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

vie. 9/12

4:48 pm-4:26 pm

1 stop23h 38m

Pensacola

dom. 9/14

5:21 pm-3:53 pm

1 stop22h 32m

$245

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

jue. 9/11

6:00 am-10:50 am

1 stop4h 50m

Pensacola

mié. 9/17

5:00 pm-9:36 pm

1 stop4h 36m

$260

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

lun. 9/15

5:30 am-10:50 am

1 stop5h 20m

Pensacola

sáb. 9/20

6:00 am-10:10 am

1 stop4h 10m

$260

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

vie. 9/12

6:00 am-4:26 pm

1 stop10h 26m

Pensacola

vie. 9/19

5:21 pm-11:59 pm

1 stop6h 38m

$268

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 9/9

6:30 am-6:10 pm

1 stop11h 40m

$79

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

sáb. 9/27

8:20 am-10:30 am

Nonstop2h 10m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 17 results
1
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Best time to book a flight from Chicago to Gulf Shores

Have a flexible travel schedule? Discover the best time to fly to Gulf Shores from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Gulf Shores?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Gulf Shores. Price data was last updated on July 25, 2025.

The price you pay for your flight from Chicago to Gulf Shores may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Gulf Shores?

Currently, September is the cheapest month in which you can book a flight from Chicago to Gulf Shores (average of $306). Flying from Chicago to Gulf Shores in March is currently the most expensive (average of $417). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to GU9?

Find hourly flight availability from Chicago to Gulf Shores. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 31, 2025.

When flying from Chicago to Gulf Shores, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Gulf Shores?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Gulf Shores. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Gulf Shores flight should consider departing on Wednesday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Gulf Shores

Explore weekly flight availability from Chicago to Gulf Shores. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated julio 31, 2025.

The most flights from CHI to GU9 are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Gulf Shores

Get insights into the airlines that provide service to Gulf Shores. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Gulf Shores. Reviews last updated julio 31, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago to Gulf Shores have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Gulf Shores. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Gulf Shores one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $79. Users have also found prices from $109 and $109 on United Airlines and Southwest, respectively.

  • What are the most reliable airlines from Chicago to Gulf Shores?

    No one likes to see their flight delayed. When booking a flight from Chicago to Gulf Shores consider choosing United Airlines (90%), Air New Zealand (90%) or Envoy Air (83%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Gulf Shores?

    On average you can expect to pay $332 for a flight from Chicago to Gulf Shores. The cheapest flight overall is $166 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $171.

  • Can I find deals for flights from Chicago to Gulf Shores that include hotel bookings?

    Yes. In addition to deals on Chicago to Gulf Shores flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Gulf Shores?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Gulf Shores.

  • Can I find deals for business class flights from Chicago to Gulf Shores?

    Yes. Cheapflights offers flight deals from Chicago to Gulf Shores by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Gulf Shores?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Gulf Shores (average of $306). Flying from Chicago to Gulf Shores in March is currently the most expensive (average of $417). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 6 airlines flying from Chicago to Gulf Shores

Discover the top 6 airlines that operate flights from Chicago to Gulf Shores. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$162FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$365FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$380FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$378FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$235Average$437FlexibilityNo cancel feeOn-time69%

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