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Gulf Shores

$61+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Gulf Shores are usually found in September or January, 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$61
(Priceline)

Popular in

March

Cheapest in

September

Average price

$299
Provider with most accurate pricing for Chicago (CHI)-Pensacola flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Pensacola flights.
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From Chicago (CHI) to Gulf Shores
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One-way flight from Chicago (CHI) to Gulf Shores
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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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 November 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 November 3, 2025.

This United Airlines deal was found by Cheapflights users on 11/1. 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.
Fri 12/510:50 amORD - PNS
Nonstop2h 27mUnited Airlines
Wed 12/102:15 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Deal found 11/1$209
This Mytrip deal was found by Cheapflights users on 10/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:48 amORD - PNS
1 stop10h 11mSpirit Airlines
Tue 12/28:16 pmPNS - ORD
1 stop13h 01mSpirit Airlines
Deal found 10/31$212
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 11/1910:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Sun 11/231:44 pmPNS - ORD
1 stop9h 22mSpirit Airlines
Deal found 11/1$213
This CheapOair deal was found by Cheapflights users on 11/1. 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.
Wed 11/1910:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Wed 11/265:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 11/1$214
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:20 pmORD - PNS
2 stops23h 44mMultiple Airlines
Wed 12/104:44 pmPNS - ORD
1 stop20h 24mMultiple Airlines
Deal found 11/1$216
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:52 amORD - PNS
1 stop8h 19mMultiple Airlines
Sat 11/154:30 pmPNS - ORD
1 stop6h 59mMultiple Airlines
Deal found 11/1$217
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:48 amORD - PNS
1 stop10h 11mSpirit Airlines
Mon 12/87:09 pmPNS - ORD
1 stop24h 52mSpirit Airlines
Deal found 11/3$219
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2511:48 amORD - PNS
1 stop7h 23mMultiple Airlines
Wed 11/268:16 pmPNS - ORD
1 stop20h 09mMultiple Airlines
Deal found 11/1$221
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Tue 11/2510:12 amORD - PNS
1 stop8h 59mSpirit Airlines
Mon 12/15:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 11/2$223
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:23 pmORD - PNS
1 stop22h 36mMultiple Airlines
Mon 12/18:16 pmPNS - ORD
1 stop26h 57mMultiple Airlines
Deal found 11/1$224
This Mytrip deal was found by Cheapflights users on 11/1. 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.
Tue 11/187:34 pmORD - PNS
2 stops23h 37mSpirit Airlines
Mon 11/245:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 11/1$227
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/310:50 amORD - PNS
Nonstop2h 27mUnited Airlines
Sun 12/72:15 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Deal found 11/2$228

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 November 3, 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

MDW - PNS

MDWPNS

Chicago Midway

Thu 12/11

6:00 am-10:41 am

1 stop4h 41m

Pensacola

Mon 12/15

6:00 am-11:55 am

1 stop5h 55m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 11/20

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Wed 11/26

2:17 pm-4:48 pm

Nonstop2h 31m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 12/1

6:00 am-10:41 am

1 stop4h 41m

Pensacola

Fri 12/5

9:29 am-4:18 pm

1 stop6h 49m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 11/20

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Mon 11/24

2:17 pm-4:48 pm

Nonstop2h 31m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 12/1

6:00 am-10:41 am

1 stop4h 41m

Pensacola

Sat 12/6

6:00 am-9:54 am

1 stop3h 54m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 2/1

6:00 am-12:45 pm

1 stop6h 45m

Pensacola

Tue 2/3

7:00 am-12:01 pm

1 stop5h 01m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 1/4

5:30 am-9:41 am

1 stop4h 11m

Pensacola

Sat 1/10

8:00 am-1:41 pm

1 stop5h 41m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 12/3

11:15 am-4:34 pm

1 stop5h 19m

Pensacola

Sun 12/7

7:15 am-12:10 pm

1 stop4h 55m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 12/19

5:30 am-12:41 pm

1 stop7h 11m

Pensacola

Sun 12/21

1:22 pm-6:59 pm

1 stop5h 37m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 1/18

5:33 am-11:33 am

1 stop6h 00m

Pensacola

Tue 2/17

1:59 pm-7:29 pm

1 stop5h 30m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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 October 31, 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, July is the cheapest month in which you can book a flight from Chicago to Gulf Shores (average of $81). Flying from Chicago to Gulf Shores in August is currently the most expensive (average of $200). 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 November 3, 2025.

When flying from Chicago to Gulf Shores, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 23% versus a flight in the afternoon.

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 Sunday mornings when fares are most often at their lowest. Monday at noon 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 November 3, 2025.

The most flights from CHI to GU9 are scheduled on a Monday (3 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chicago to Gulf Shores?

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 November 3, 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
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,115 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

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 26m. Delta provides one of the quickest options available for as low as $229. 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 flights from Chicago to Gulf Shores?

    On average you can expect to pay $271 for a flight from Chicago to Gulf Shores. The cheapest flight overall is $104 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $183.

  • 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, July is the cheapest month in which you can book a flight from Chicago to Gulf Shores (average of $81). Flying from Chicago to Gulf Shores in August is currently the most expensive (average of $200). 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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Alternative routes for Chicago to Gulf Shores

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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$168FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$392FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$385FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$400FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$410FlexibilityNo cancel feeOn-time69%

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