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Gulf Shores

$69+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$166
(Cheapflightsfares)

One-way from

$69
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$375
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 ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/135:05 amORD - PNS
1 stop10h 25mSpirit Airlines
Sat 5/176:14 pmPNS - ORD
1 stop5h 15mSpirit Airlines
Deal found 4/29$166
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/1310:40 amORD - PNS
Nonstop2h 28mUnited Airlines
Sat 5/172:05 pmPNS - ORD
Nonstop2h 41mUnited Airlines
Deal found 4/29$177
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/136:45 amMDW - PNS
1 stop4h 00mSouthwest
Sat 5/174:15 pmPNS - MDW
Nonstop2h 10mSouthwest
Deal found 4/29$187
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 6/146:15 pmORD - PNS
1 stop5h 05mDelta
Wed 6/186:00 amPNS - ORD
1 stop4h 09mDelta
Deal found 4/30$197
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 6/74:15 pmMDW - PNS
1 stop5h 21mDelta
Mon 6/164:07 pmPNS - MDW
1 stop5h 38mDelta
Deal found 4/30$197
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/188:15 amORD - PNS
Nonstop2h 24mAmerican Airlines
Sun 5/2512:07 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 4/30$203
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 5/281:50 pmORD - PNS
2 stops8h 20mSouthwest
Wed 6/48:00 amPNS - ORD
1 stop4h 45mSouthwest
Deal found 4/30$252
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Thu 5/811:45 amORD - PNS
2 stops19h 40mMultiple Airlines
Sat 5/106:14 pmPNS - ORD
1 stop5h 15mMultiple Airlines
Deal found 4/30$283
This Frontier deal was found by Cheapflights users on 4/30. 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.
Fri 5/306:00 amORD - PNS
1 stop9h 23mFrontier
Mon 6/24:29 pmPNS - ORD
1 stop7h 30mFrontier
Deal found 4/30$290
This Gotogate deal was found by Cheapflights users on 4/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1312:35 pmMDW - PNS
1 stop26h 54mFrontier
Fri 6/204:29 pmPNS - MDW
1 stop28h 24mFrontier
Deal found 4/30$436

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 May 1, 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

Tue 5/13

5:05 am-3:30 pm

1 stop10h 25m

Pensacola

Sat 5/17

6:14 pm-11:29 pm

1 stop5h 15m

$166

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 5/13

10:40 am-1:08 pm

Nonstop2h 28m

Pensacola

Sat 5/17

2:05 pm-4:46 pm

Nonstop2h 41m

$177

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 5/13

6:45 am-10:45 am

1 stop4h 00m

Pensacola

Sat 5/17

4:15 pm-6:25 pm

Nonstop2h 10m

$187

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 6/14

6:15 pm-11:20 pm

1 stop5h 05m

Pensacola

Wed 6/18

6:00 am-10:09 am

1 stop4h 09m

$197

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 6/7

4:15 pm-9:36 pm

1 stop5h 21m

Pensacola

Mon 6/16

4:07 pm-9:45 pm

1 stop5h 38m

$197

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 5/18

8:15 am-10:39 am

Nonstop2h 24m

Pensacola

Sun 5/25

12:07 pm-2:49 pm

Nonstop2h 42m

$203

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 5/28

1:50 pm-10:10 pm

2 stops8h 20m

Pensacola

Wed 6/4

8:00 am-12:45 pm

1 stop4h 45m

$252

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 5/8

11:45 am-7:25 am

2 stops19h 40m

Pensacola

Sat 5/10

6:14 pm-11:29 pm

1 stop5h 15m

$283

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 5/30

6:00 am-3:23 pm

1 stop9h 23m

Pensacola

Mon 6/2

4:29 pm-11:59 pm

1 stop7h 30m

$290

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 6/13

12:35 pm-3:29 pm

1 stop26h 54m

Pensacola

Fri 6/20

4:29 pm-8:53 pm

1 stop28h 24m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 21 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 April 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 $418). 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 May 1, 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.

Rainfall in Gulf Shores by month

Plan your trip to Gulf Shores by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Gulf Shores ranges from 4.2 - 7.4 inches per month. July is typically the wettest month, when rainfall can reach 7.4 in. May is typically the driest time to visit Gulf Shores when rainfall is around 4.2 in.

Temperature in Gulf Shores by month

Plan your trip to Gulf Shores by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Gulf Shores, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 May 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Chicago to Gulf Shores to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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
7,962 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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 $69. Users have also found prices from $89 and $89 on American 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 American Airlines (100%), Envoy Air (100%) or Spirit Airlines (89%) 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 $315 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 $146.

  • 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 $418). 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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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$92Average$167FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$205FlexibilityNo cancel feeOn-time65%
DeltaCheapest$199Average$333FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$383FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$430FlexibilityNo cancel feeOn-time69%

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