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Gulf Shores

$53+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Dec 29 — Jan 51
Sun 12/29
Sun 1/5
1 adult, Economy
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The best prices from Chicago to Gulf Shores are usually found in January or April, booked 63 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Chicago to Gulf Shores

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Gulf Shores (GU9). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 24, 2024.

Round-trip from

$228
(Delta)

One-way from

$53
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$445
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, 1% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in December 2024
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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 December 24, 2024.

This American Airlines deal was found by Cheapflights users on 12/23. 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.
Mon 12/308:05 amORD - PNS
1 stop7h 21mAmerican Airlines
Mon 1/133:54 pmPNS - ORD
1 stop6h 10mAmerican Airlines
Deal found 12/23$263
This United Airlines deal was found by Cheapflights users on 12/23. 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 12/3110:50 amORD - PNS
Nonstop2h 30mUnited Airlines
Tue 1/142:31 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Deal found 12/23$299
This FlightHub deal was found by Cheapflights users on 12/22. 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.
Tue 12/313:31 pmORD - PNS
1 stop26h 34mMultiple Airlines
Sun 1/58:21 pmPNS - ORD
1 stop27h 25mMultiple Airlines
Deal found 12/22$306
This Mytrip deal was found by Cheapflights users on 12/23. 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 12/318:14 pmORD - PNS
2 stops21h 51mSpirit Airlines
Tue 1/142:18 pmPNS - ORD
3 stops22h 21mSpirit Airlines
Deal found 12/23$314
This Delta deal was found by Cheapflights users on 12/23. 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.
Wed 12/2510:08 amMDW - PNS
1 stop5h 20mDelta
Tue 12/314:13 pmPNS - MDW
1 stop5h 53mDelta
Deal found 12/23$358
This Delta deal was found by Cheapflights users on 12/22. 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.
Wed 12/255:57 pmORD - PNS
1 stop5h 01mDelta
Tue 12/3111:47 amPNS - ORD
1 stop4h 28mDelta
Deal found 12/22$408
This Southwest deal was found by Cheapflights users on 12/23. 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 12/257:30 amORD - PNS
2 stops8h 20mSouthwest
Tue 12/318:45 amPNS - ORD
2 stops9h 25mSouthwest
Deal found 12/23$423
This Southwest deal was found by Cheapflights users on 12/23. 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 12/257:15 amMDW - PNS
2 stops11h 35mSouthwest
Tue 12/318:45 amPNS - MDW
1 stop8h 50mSouthwest
Deal found 12/23$453

Find flights from Chicago to Gulf Shores within your budget

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 December 24, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 4/16

7:10 am-2:23 pm

1 stop7h 13m

Pensacola

Wed 4/23

3:35 pm-9:14 pm

1 stop5h 39m

$228

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 1/21

10:57 am-4:58 pm

1 stop6h 01m

Pensacola

Tue 1/28

9:41 am-4:21 pm

1 stop6h 40m

$228

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/7

10:53 am-1:23 pm

Nonstop2h 30m

Pensacola

Sat 1/11

3:10 pm-10:45 pm

1 stop7h 35m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/14

3:56 pm-1:23 pm

3 stops21h 27m

Pensacola

Tue 1/21

2:18 pm-12:39 pm

3 stops22h 21m

$231

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 1/16

7:15 am-6:17 pm

1 stop11h 02m

Pensacola

Sun 1/19

7:17 pm-12:17 am

1 stop29h 00m

$240

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 2/27

6:00 am-3:45 pm

1 stop9h 45m

Pensacola

Mon 3/3

5:37 pm-9:33 pm

3 stops27h 56m

$255

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 4/25

5:24 pm-11:34 pm

1 stop6h 10m

Pensacola

Tue 4/29

11:20 am-5:36 pm

1 stop6h 16m

$258

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 2/13

6:50 am-6:27 pm

1 stop11h 37m

Pensacola

Mon 2/17

7:27 pm-1:25 pm

1 stop17h 58m

$278

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 2/21

7:30 am-3:50 pm

2 stops8h 20m

Pensacola

Tue 2/25

8:20 am-4:45 pm

1 stop8h 25m

$293

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/21

12:00 pm-5:20 pm

1 stop5h 20m

Pensacola

Sun 2/23

2:20 pm-11:20 pm

2 stops9h 00m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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.

Travel insights for flights from Chicago to Gulf Shores

Get recent, data-driven insights about flights from Chicago to Gulf Shores including ideal travel times, pricing trends, and more.

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 December 20, 2024.

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 63 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 December 24, 2024.

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. Monday 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 December 24, 2024.
Peruse reviews from past customers who have flown with United Airlines, American Airlines and Spirit 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
8.1
Very good
4,765 reviews

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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
8.1
Very good
4,765 reviews
Southwest
8.1
Very good
4,765 reviews

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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
8,588 reviews
Southwest
8.1
Very good
4,765 reviews

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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
9,020 reviews
Southwest
8.1
Very good
4,765 reviews

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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
8.1
Very good
4,765 reviews

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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
8,107 reviews
Southwest
8.1
Very good
4,765 reviews

Food

7.2

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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 Frontier. According to our data, you can fly for as low as $53. Users have also found prices from $80 and $105 on Spirit Airlines and United Airlines, 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 SkyWest Airlines (92%), United Airlines (83%) or Air New Zealand (82%) 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 $363 for a flight from Chicago to Gulf Shores. The cheapest flight overall is $139 while the most popular route, (Chicago O'Hare Intl - Pensacola) is currently priced at $147.

  • 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.

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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 December 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$175FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$100Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$143Average$395FlexibilityNo cancel feeOn-time63%
DeltaCheapest$199Average$382FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$365FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$241Average$423FlexibilityNo cancel feeOn-time69%
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