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Gulfport

$215+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
ago. 26 — sep. 21
mar. 8/26
mar. 9/2
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 agosto 21, 2025.

Round-trip from

$249
(Delta)

One-way from

$215
(Delta)

Popular in

February

Cheapest in

August

Average price

$266
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. 11% potential increase in price ($56 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 August 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 agosto 21, 2025.

This Delta deal was found by Cheapflights users on 8/20. 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.
sáb. 9/274:25 pmMDW - GPT
1 stop5h 14mDelta
mié. 10/16:08 amGPT - MDW
1 stop5h 40mDelta
Deal found 8/20$249
This American Airlines deal was found by Cheapflights users on 8/20. 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.
sáb. 10/256:45 amORD - GPT
1 stop6h 09mAmerican Airlines
mar. 10/281:15 pmGPT - ORD
1 stop6h 25mAmerican Airlines
Deal found 8/20$249
This American Airlines deal was found by Cheapflights users on 8/19. 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.
jue. 9/46:30 pmORD - GPT
1 stop5h 07mAmerican Airlines
vie. 9/125:32 pmGPT - ORD
1 stop5h 40mAmerican Airlines
Deal found 8/19$254
This Delta deal was found by Cheapflights users on 8/21. 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.
mié. 9/34:25 pmMDW - GPT
1 stop5h 13mDelta
sáb. 9/63:45 pmGPT - MDW
1 stop5h 27mDelta
Deal found 8/21$259
This Delta deal was found by Cheapflights users on 8/18. 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.
sáb. 9/277:10 amORD - GPT
2 stops14h 29mDelta
mié. 10/16:04 pmGPT - ORD
1 stop4h 10mDelta
Deal found 8/18$297
This American Airlines deal was found by Cheapflights users on 8/21. 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.
vie. 9/126:30 pmORD - GPT
1 stop5h 02mAmerican Airlines
lun. 9/156:29 pmGPT - ORD
1 stop5h 30mAmerican Airlines
Deal found 8/21$318
This American Airlines deal was found by Cheapflights users on 8/20. 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.
sáb. 9/2710:01 amORD - GPT
1 stop7h 58mAmerican Airlines
mié. 10/112:12 pmGPT - ORD
1 stop5h 06mAmerican Airlines
Deal found 8/20$319
This Delta deal was found by Cheapflights users on 8/20. 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.
sáb. 8/234:25 pmMDW - GPT
1 stop5h 13mDelta
mar. 8/265:00 pmGPT - MDW
1 stop4h 44mDelta
Deal found 8/20$339
This Delta deal was found by Cheapflights users on 8/20. 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.
sáb. 8/239:47 amORD - GPT
1 stop5h 12mDelta
mar. 8/265:00 pmGPT - ORD
1 stop5h 37mDelta
Deal found 8/20$339
This United Airlines deal was found by Cheapflights users on 8/21. 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.
mié. 9/38:45 amORD - GPT
1 stop5h 28mUnited Airlines
sáb. 9/62:02 pmGPT - ORD
1 stop5h 56mUnited Airlines
Deal found 8/21$354
This United Airlines deal was found by Cheapflights users on 8/19. 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.
jue. 9/48:45 amORD - GPT
1 stop7h 20mUnited Airlines
vie. 9/125:00 pmGPT - ORD
2 stops18h 52mUnited Airlines
Deal found 8/19$367
This Delta deal was found by Cheapflights users on 8/21. 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.
vie. 9/197:20 amORD - GPT
1 stop6h 00mDelta
lun. 9/222:05 pmGPT - ORD
1 stop7h 20mDelta
Deal found 8/21$374

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 agosto 21, 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

sáb. 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

mié. 10/1

6:08 am-11:48 am

1 stop5h 40m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

sáb. 10/25

6:45 am-12:54 pm

1 stop6h 09m

Gulfport Biloxi Regional

mar. 10/28

1:15 pm-7:40 pm

1 stop6h 25m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

jue. 9/4

6:30 pm-11:37 pm

1 stop5h 07m

Gulfport Biloxi Regional

vie. 9/12

5:32 pm-11:12 pm

1 stop5h 40m

$254

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

mié. 9/3

4:25 pm-9:38 pm

1 stop5h 13m

Gulfport Biloxi Regional

sáb. 9/6

3:45 pm-9:12 pm

1 stop5h 27m

$259

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

sáb. 9/27

7:10 am-9:39 pm

2 stops14h 29m

Gulfport Biloxi Regional

mié. 10/1

6:04 pm-10:14 pm

1 stop4h 10m

$297

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

vie. 9/12

6:30 pm-11:32 pm

1 stop5h 02m

Gulfport Biloxi Regional

lun. 9/22

6:29 pm-11:59 pm

1 stop5h 30m

$318

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

vie. 9/12

6:30 pm-11:32 pm

1 stop5h 02m

Gulfport Biloxi Regional

lun. 9/15

2:01 pm-8:27 pm

1 stop6h 26m

$318

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

jue. 10/2

5:00 am-12:22 pm

1 stop7h 22m

Gulfport Biloxi Regional

dom. 10/5

6:34 pm-11:39 pm

1 stop5h 05m

$318

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

vie. 9/12

6:30 pm-11:32 pm

1 stop5h 02m

Gulfport Biloxi Regional

vie. 9/19

6:29 pm-11:59 pm

1 stop5h 30m

$318

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

jue. 9/18

6:00 am-11:42 am

1 stop5h 42m

Gulfport Biloxi Regional

jue. 9/25

6:34 pm-11:39 pm

1 stop5h 05m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 20 results
1
2

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 $416). 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.

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 agosto 21, 2025.
Peruse reviews from past customers who have flown with Delta 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
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 and American Airlines can get you from Chicago to Gulfport in just under 5h 14m. Your travel time can differ by up to 55m. 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 $253 round trip. You may be able to fly from Chicago to Gulfport for 41% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Gulfport one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $215. Users have also found prices from $215 and $273 on Delta and United Airlines, respectively.

  • 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 $416). 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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Alternative routes for Chicago to Gulfport

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 agosto 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$368FlexibilityNo cancel feeOn-time71%
DeltaCheapest$253Average$423FlexibilityNo cancel feeOn-timeN/A

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