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$100+ Cheap flights from Chicago (CHI) to Gulfport (GPT)

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 — GPT
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Chicago to Gulfport

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Gulfport (GPT). 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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$356
Provider with most accurate pricing for Chicago (CHI)-Gulfport Biloxi Regional flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Gulfport Biloxi Regional flights.
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From Chicago (CHI) to Gulfport Biloxi Regional
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One-way flight from Chicago (CHI) to Gulfport Biloxi Regional
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Highest demand for flights based on searches. 13% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chicago to Gulfport

Cheapest flights from Chicago to Gulfport
Explore the most affordable flight options available from Chicago to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This Delta deal was found by Cheapflights users on 4/17. 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.
Fri 7/43:40 pmORD - GPT
1 stop6h 18mDelta
Tue 7/82:15 pmGPT - ORD
1 stop4h 48mDelta
Deal found 4/17$233
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Sat 5/171:58 pmORD - GPT
1 stop5h 28mAmerican Airlines
Sat 5/246:25 amGPT - ORD
1 stop7h 41mAmerican Airlines
Deal found 4/17$279
This Delta deal was found by Cheapflights users on 4/16. 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 5/314:15 pmMDW - GPT
1 stop5h 21mDelta
Sat 6/79:14 amGPT - MDW
1 stop6h 06mDelta
Deal found 4/16$284
This United Airlines deal was found by Cheapflights users on 4/17. 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 4/282:18 pmORD - GPT
1 stop5h 28mUnited Airlines
Sat 5/34:55 pmGPT - ORD
1 stop6h 03mUnited Airlines
Deal found 4/17$284
This Mytrip deal was found by Cheapflights users on 4/17. 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.
Sun 6/16:30 amORD - GPT
1 stop25h 15mMultiple Airlines
Sun 6/812:55 pmGPT - ORD
3 stops30h 22mMultiple Airlines
Deal found 4/17$605

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Gulfport 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 April 17, 2025.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.

Fly from

Chicago

Fly to

Gulfport

Route

Depart

Return

Price

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 5/31

12:08 pm-5:47 pm

1 stop5h 39m

Gulfport Biloxi Regional

Sat 6/7

7:43 pm-12:59 am

1 stop5h 16m

$224

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 5/24

4:25 pm-9:36 pm

1 stop5h 11m

Gulfport Biloxi Regional

Wed 5/28

6:05 pm-11:58 pm

1 stop5h 53m

$238

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 4/28

2:18 pm-7:46 pm

1 stop5h 28m

Gulfport Biloxi Regional

Sat 5/3

4:55 pm-10:58 pm

1 stop6h 03m

$284

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 5/31

4:15 pm-9:36 pm

1 stop5h 21m

Gulfport Biloxi Regional

Sat 6/7

9:14 am-3:20 pm

1 stop6h 06m

$284

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 4/30

7:47 pm-5:49 pm

2 stops22h 02m

Gulfport Biloxi Regional

Mon 6/2

5:37 pm-8:08 pm

1 stop26h 31m

$441

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 5/31

10:34 am-5:47 pm

1 stop7h 13m

$100

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 5/31

4:15 pm-9:36 pm

1 stop5h 21m

$160

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 5/12

9:20 pm-1:26 pm

2 stops16h 06m

$278

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 5/31

9:02 pm-7:45 am

3 stops34h 43m

$554

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 4/26

1:25 pm-10:08 pm

2 stops8h 43m

$867

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Compare providers for flights from Chicago to Gulfport

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Gulfport in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Gulfport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Gulfport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Gulfport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Gulfport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Gulfport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Gulfport

Have a flexible travel schedule? Discover the best time to fly to Gulfport 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 Gulfport

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $423). 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.

Rainfall in Gulfport by month

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

In terms of precipitation, rainfall in Gulfport ranges from 3.6 - 7.2 inches per month. July is typically the wettest month, when rainfall can reach 7.2 in. October is typically the driest time to visit Gulfport when rainfall is around 3.6 in.

Temperature in Gulfport by month

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

If weather is an important factor for your trip to Gulfport, 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 50.0 F).

Reviews of airlines servicing Gulfport

Get insights into the airlines that provide service to Gulfport. 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 Gulfport. Reviews last updated April 17, 2025.
Get a feel of what it's like to fly with Delta, United Airlines and American Airlines from Chicago to Gulfport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,916 reviews
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,667 reviews
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,916 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

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

  • What airport do you fly into for flights to Gulfport from Chicago?

    Gulfport Biloxi Regional (GPT), located 3.1 mi from the city center, is the airport you fly into when you book flights from Chicago to Gulfport. 2 airlines have flights to Biloxi Regional from Chicago on a regular basis. Booking flights from Chicago to Gulfport Biloxi Regional should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • What are the cheapest airlines flying from Chicago to Gulfport round-trip?

    Flying on American Airlines is currently your cheapest option to Gulfport, with prices starting at $224. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $238 and $284, respectively. You may be able to fly from Chicago to Gulfport for 46% less than the average price by searching for these airlines.

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

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

  • How can I find direct flights from Chicago to Gulfport?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Gulfport 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 Gulfport?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $423). 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 2 airlines flying from Chicago to Gulfport

Discover the top 2 airlines that operate flights from Chicago to Gulfport. 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$257Average$462FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$263Average$402FlexibilityNo cancel feeOn-time71%

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