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$121+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
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 November 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$121
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$461
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
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($99 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 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 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 November 25, 2025.

This Delta deal was found by Cheapflights users on 11/24. 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.
Thu 12/189:49 amORD - GPT
1 stop4h 19mDelta
Thu 12/255:21 pmGPT - ORD
1 stop6h 41mDelta
Deal found 11/24$249
This Delta deal was found by Cheapflights users on 11/23. 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 12/109:49 amORD - GPT
1 stop4h 19mDelta
Fri 12/265:21 pmGPT - ORD
1 stop6h 42mDelta
Deal found 11/23$264
This Delta deal was found by Cheapflights users on 11/24. 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 12/134:29 pmMDW - GPT
1 stop5h 34mDelta
Mon 12/156:01 pmGPT - MDW
1 stop5h 46mDelta
Deal found 11/24$304
This Delta deal was found by Cheapflights users on 11/23. 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.
Thu 12/115:30 amORD - GPT
1 stop4h 20mDelta
Fri 12/265:21 pmGPT - ORD
1 stop6h 42mDelta
Deal found 11/23$304
This Delta deal was found by Cheapflights users on 11/24. 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 12/64:29 pmMDW - GPT
1 stop5h 34mDelta
Tue 12/96:01 pmGPT - MDW
1 stop5h 46mDelta
Deal found 11/24$309
This Delta deal was found by Cheapflights users on 11/24. 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 12/64:20 pmORD - GPT
1 stop5h 43mDelta
Tue 12/96:00 amGPT - ORD
1 stop4h 14mDelta
Deal found 11/24$309
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Wed 12/2412:39 pmORD - GPT
2 stops30h 31mMultiple Airlines
Mon 12/296:51 pmGPT - ORD
1 stop13h 30mMultiple Airlines
Deal found 11/24$315
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/225:28 pmORD - GPT
1 stop6h 44mAmerican Airlines
Mon 12/295:58 pmGPT - ORD
1 stop5h 17mAmerican Airlines
Deal found 11/24$339
This Delta deal was found by Cheapflights users on 11/23. 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 12/105:29 pmMDW - GPT
1 stop4h 34mDelta
Fri 12/265:21 pmGPT - MDW
1 stop5h 01mDelta
Deal found 11/23$343
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:09 pmORD - GPT
1 stop7h 06mMultiple Airlines
Fri 12/266:51 pmGPT - ORD
2 stops27h 54mMultiple Airlines
Deal found 11/23$353
This Delta deal was found by Cheapflights users on 11/24. 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 11/265:23 amORD - GPT
1 stop4h 26mDelta
Mon 12/16:03 pmGPT - ORD
1 stop5h 59mDelta
Deal found 11/24$354
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:09 pmORD - GPT
1 stop7h 06mMultiple Airlines
Sun 12/287:50 pmGPT - ORD
2 stops15h 40mMultiple Airlines
Deal found 11/23$358

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 November 25, 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

MDW - GPT

MDWGPT

Chicago Midway

Wed 1/7

5:31 pm-9:53 pm

1 stop4h 22m

Gulfport Biloxi Regional

Sat 1/10

6:05 am-10:32 am

1 stop4h 27m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/7

10:35 am-3:58 pm

1 stop5h 23m

Gulfport Biloxi Regional

Sat 1/10

5:13 pm-12:28 am

1 stop7h 15m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 12/13

5:34 pm-11:53 pm

1 stop6h 19m

Gulfport Biloxi Regional

Mon 12/15

6:13 pm-11:35 pm

1 stop5h 22m

$264

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 12/10

9:49 am-2:08 pm

1 stop4h 19m

Gulfport Biloxi Regional

Fri 12/26

5:21 pm-12:03 am

1 stop6h 42m

$264

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/7

9:55 am-3:09 pm

1 stop5h 14m

Gulfport Biloxi Regional

Sat 1/10

6:05 am-1:39 pm

1 stop7h 34m

$274

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 12/13

4:29 pm-10:03 pm

1 stop5h 34m

Gulfport Biloxi Regional

Mon 12/15

6:01 pm-11:47 pm

1 stop5h 46m

$304

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 12/11

5:30 am-9:50 am

1 stop4h 20m

Gulfport Biloxi Regional

Fri 12/26

5:21 pm-12:03 am

1 stop6h 42m

$304

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 12/11

5:18 am-11:32 am

1 stop6h 14m

Gulfport Biloxi Regional

Sat 12/27

4:48 pm-11:59 pm

1 stop7h 11m

$309

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 12/6

4:29 pm-10:03 pm

1 stop5h 34m

Gulfport Biloxi Regional

Tue 12/9

6:01 pm-11:47 pm

1 stop5h 46m

$309

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 12/6

4:20 pm-10:03 pm

1 stop5h 43m

Gulfport Biloxi Regional

Tue 12/9

6:00 am-10:14 am

1 stop4h 14m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 24 results
1
2
3

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Gulfport flight deals on Cheapflights vs. eDreams >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, June is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $80). Flying from Chicago to Gulfport in July is currently the most expensive (average of $161). 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.

How often are flights from Chicago to Gulfport delayed?

About 42% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 89 minutes.

What is the most punctual flight time for Chicago to Gulfport flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Friday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Gulfport flights?

Over the last year, Sun Country Air have had the lowest number of delays on this route, with just 53% of flights being delayed.

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 November 25, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Gulfport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,046 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,038 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Chicago to Gulfport?

    Delta, United Airlines, and American Airlines can get you from Chicago to Gulfport in just under 4h 22m. Your travel time can differ by up to 1h 57m. The distance from Chicago to Gulfport is about 789 mi. This flight may include one or multiple stops.

  • 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 $248. Another option worth looking into is Delta, starting at $248 round trip. You may be able to fly from Chicago to Gulfport for 41% 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, June is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $80). Flying from Chicago to Gulfport in July is currently the most expensive (average of $161). 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

Traveling to a place near Gulfport?

Book flights to Gulfport if you plan to visit one of these locations
Ocean Springs

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See prices for flight routes from nearby airports that may be better suited for you.
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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 November 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$336FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$405FlexibilityNo cancel feeOn-timeN/A

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