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Gulf Shores

$70+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 16 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 September 15, 2025.

Round-trip from

$203
(American Airlines)

One-way from

$70
(Southwest)

Popular in

December

Cheapest in

January

Average price

$304
From Chicago (CHI) to Gulf Shores
Search Deals
One-way flight from Chicago (CHI) to Gulf Shores
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
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 September 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 11/1910:30 amORD - PNS
Nonstop2h 30mAmerican Airlines
Mon 11/241:17 pmPNS - ORD
Nonstop2h 38mAmerican Airlines
Deal found 9/14$203
This Frontier deal was found by Cheapflights users on 9/14. 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.
Sun 10/266:50 amORD - PNS
1 stop9h 40mFrontier
Mon 11/35:07 pmPNS - ORD
1 stop7h 08mFrontier
Deal found 9/14$204
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:41 amORD - PNS
1 stop6h 55mSpirit Airlines
Sun 11/94:41 pmPNS - ORD
1 stop7h 01mSpirit Airlines
Deal found 9/13$206
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Mon 11/310:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Sat 11/152:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 9/13$209
This Frontier deal was found by Cheapflights users on 9/14. 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.
Fri 10/316:00 amORD - PNS
1 stop9h 35mFrontier
Fri 11/74:30 pmPNS - ORD
1 stop7h 45mFrontier
Deal found 9/14$210
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/125:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Sun 10/194:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/14$211
This Frontier deal was found by Cheapflights users on 9/13. 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.
Sat 11/17:15 amORD - PNS
1 stop8h 20mFrontier
Sat 11/154:30 pmPNS - ORD
1 stop7h 42mFrontier
Deal found 9/13$213
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Sat 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/14$214
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/211:26 pmORD - PNS
1 stop5h 51mDelta
Wed 10/297:00 amPNS - ORD
1 stop5h 16mDelta
Deal found 9/15$217
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 10/88:40 amMDW - PNS
1 stop6h 45mSouthwest
Tue 10/1410:10 amPNS - MDW
1 stop5h 45mSouthwest
Deal found 9/14$217
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 11/1910:50 amMDW - PNS
1 stop4h 45mSouthwest
Wed 11/269:50 amPNS - MDW
1 stop7h 00mSouthwest
Deal found 9/15$218
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:00 amORD - PNS
1 stop11h 01mSpirit Airlines
Sun 10/194:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/13$219

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 September 15, 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

Fri 10/3

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Wed 10/8

2:17 pm-4:54 pm

Nonstop2h 37m

$213

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 10/8

8:40 am-3:25 pm

1 stop6h 45m

Pensacola

Tue 10/14

10:10 am-3:55 pm

1 stop5h 45m

$217

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 10/21

6:45 am-10:39 am

1 stop3h 54m

Pensacola

Wed 10/29

6:00 am-12:16 pm

1 stop6h 16m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/19

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Wed 11/26

9:50 am-4:50 pm

1 stop7h 00m

$218

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 11/4

10:40 am-3:05 pm

1 stop4h 25m

Pensacola

Fri 11/14

6:00 am-9:51 am

1 stop3h 51m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 10/26

5:35 am-9:10 am

1 stop3h 35m

Pensacola

Wed 10/29

2:30 pm-6:10 pm

1 stop3h 40m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 12/2

9:50 am-4:35 pm

1 stop6h 45m

Pensacola

Thu 12/4

5:45 pm-9:53 pm

1 stop4h 08m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 10/8

8:40 am-3:25 pm

1 stop6h 45m

Pensacola

Mon 10/13

7:35 pm-11:15 pm

1 stop3h 40m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 9/27

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Tue 9/30

2:17 pm-4:54 pm

Nonstop2h 37m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 11/8

6:00 am-12:52 pm

1 stop6h 52m

Pensacola

Sat 11/15

4:30 pm-11:32 pm

1 stop7h 02m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 42 results
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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 September 12, 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 16 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 $303). Flying from Chicago to Gulf Shores in March is currently the most expensive (average of $415). 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 September 15, 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 September 15, 2025.

The most flights from CHI to GU9 are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, 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 September 15, 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
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the 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.

  • How long is the flight from Chicago to Gulf Shores?

    A quick flight from Chicago to Gulf Shores can take about 2h 25m. United Airlines provides one of the quickest options available for as low as $213. The distance from Chicago to Gulf Shores is about 795 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $89. Users have also found prices from $91 and $104 on Spirit 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 American Airlines (80%) 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 $368 for a flight from Chicago to Gulf Shores. The cheapest flight overall is $107 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $177.

  • 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 $303). Flying from Chicago to Gulf Shores in March is currently the most expensive (average of $415). 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.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$138FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$399FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$225Average$395FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$416FlexibilityNo cancel feeOn-time69%

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