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$121+ Cheap flights from Gulfport (GPT) to Chicago (CHI)

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Gulfport to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Gulfport (GPT) to Chicago (CHI). 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 September 11, 2025.

Round-trip from

$249
(Delta)

One-way from

$121
(Kiwi.com)

Popular in

February

Cheapest in

April

Average price

$497
From Gulfport Biloxi Regional to Chicago (CHI)
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One-way flight from Gulfport Biloxi Regional to Chicago (CHI)
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Highest demand for flights based on searches. 14% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Gulfport to Chicago

Cheapest flights from Gulfport to Chicago
Explore the most affordable flight options available from Gulfport to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 11/153:30 pmGPT - ORD
1 stop6h 23mDelta
Tue 11/1811:14 amORD - GPT
1 stop5h 59mDelta
Deal found 9/10$249
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 10/26:34 pmGPT - ORD
1 stop5h 05mAmerican Airlines
Wed 10/86:45 amORD - GPT
1 stop6h 00mAmerican Airlines
Deal found 9/9$250
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 9/266:29 pmGPT - ORD
1 stop5h 30mAmerican Airlines
Tue 9/304:12 pmORD - GPT
1 stop7h 20mAmerican Airlines
Deal found 9/9$254
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 10/206:51 pmGPT - ORD
1 stop15h 17mMultiple Airlines
Wed 10/226:58 pmORD - GPT
1 stop24h 17mMultiple Airlines
Deal found 9/9$259
This Delta deal was found by Cheapflights users on 9/10. 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 9/266:04 pmGPT - ORD
1 stop5h 50mDelta
Tue 9/307:20 amORD - GPT
1 stop6h 00mDelta
Deal found 9/10$284
This Delta deal was found by Cheapflights users on 9/11. 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 12/245:15 pmGPT - ORD
1 stop6h 43mDelta
Sat 12/275:40 amORD - GPT
1 stop4h 51mDelta
Deal found 9/11$294
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 9/186:34 pmGPT - ORD
1 stop5h 05mAmerican Airlines
Mon 9/225:08 pmORD - GPT
1 stop5h 34mAmerican Airlines
Deal found 9/11$309
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/35:32 pmGPT - ORD
1 stop5h 40mAmerican Airlines
Sun 10/56:00 amORD - GPT
1 stop5h 42mAmerican Airlines
Deal found 9/10$314
This Delta deal was found by Cheapflights users on 9/10. 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 12/610:35 amGPT - MDW
2 stops22h 44mDelta
Tue 12/912:50 pmMDW - GPT
1 stop4h 24mDelta
Deal found 9/10$316
This American Airlines deal was found by Cheapflights users on 9/8. 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 12/134:41 pmGPT - ORD
1 stop7h 20mAmerican Airlines
Tue 12/167:25 amORD - GPT
1 stop5h 07mAmerican Airlines
Deal found 9/8$319
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 10/206:05 pmGPT - MDW
1 stop4h 09mDelta
Wed 10/2210:35 amMDW - GPT
1 stop6h 45mDelta
Deal found 9/10$539
This Delta deal was found by Cheapflights users on 9/9. 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 9/266:08 amGPT - MDW
1 stop5h 40mDelta
Tue 9/3010:35 amMDW - GPT
1 stop6h 44mDelta
Deal found 9/9$549

Cheapflights Fare Finder

 
Customize your flight search to find flights from Gulfport to Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from Gulfport to Chicago that are best for you.

Fly from

Gulfport

Fly to

Chicago

Route

Depart

Return

Price

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 11/15

3:30 pm-9:53 pm

1 stop6h 23m

Chicago O'Hare Intl

Tue 11/18

11:14 am-5:13 pm

1 stop5h 59m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 10/20

6:51 pm-10:08 am

1 stop15h 17m

Chicago O'Hare Intl

Wed 10/22

7:43 pm-7:15 pm

2 stops23h 32m

$282

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/26

6:04 pm-11:54 pm

1 stop5h 50m

Chicago O'Hare Intl

Tue 9/30

11:20 am-5:19 pm

1 stop5h 59m

$284

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 12/24

5:15 pm-11:58 pm

1 stop6h 43m

Chicago O'Hare Intl

Sat 12/27

5:40 am-10:31 am

1 stop4h 51m

$294

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 12/6

10:35 am-9:19 am

2 stops22h 44m

Chicago Midway

Tue 12/9

12:50 pm-5:14 pm

1 stop4h 24m

$316

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/26

6:04 pm-11:54 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 9/29

3:35 pm-9:39 pm

1 stop6h 04m

$324

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 12/11

6:01 pm-12:01 am

1 stop6h 00m

Chicago O'Hare Intl

Sat 12/13

5:32 am-9:50 am

1 stop4h 18m

$328

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 11/21

6:03 pm-12:02 am

1 stop5h 59m

Chicago O'Hare Intl

Sun 11/23

6:45 am-2:08 pm

1 stop7h 23m

$328

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Mon 10/20

6:05 pm-10:14 pm

1 stop4h 09m

Chicago Midway

Wed 10/22

10:35 am-5:20 pm

1 stop6h 45m

$539

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 9/26

6:08 am-11:48 am

1 stop5h 40m

Chicago Midway

Tue 9/30

10:35 am-5:19 pm

1 stop6h 44m

$549

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 24 results
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Best time to book a flight from Gulfport to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $245). Flying from Gulfport to Chicago in March is currently the most expensive (average of $321). 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 much does it cost to fly round-trip from Gulfport to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 11, 2025.
See what other customers who have flown with Delta and American Airlines from Gulfport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

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
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

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 Gulfport to Chicago. 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 from for flights from Gulfport to Chicago?

    For a flight from Gulfport to Chicago, you will be flying from Biloxi Regional. Gulfport Biloxi Regional (GPT) is just 3.1 mi from the center of the city. Biloxi Regional is the only Gulfport airport and it handles 0 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Gulfport Biloxi Regional on a regular basis.

  • How long is the flight from Gulfport to Chicago?

    A quick flight from Gulfport to Chicago can take about 6h 23m. Delta provides one of the quickest options available for as low as $249. There are 802 mi between Gulfport and Chicago.

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

    According to our current data, Delta ($116), and American Airlines ($248) offers the cheapest pricing from Gulfport to Chicago. These flights start at 73% lower than the current average price 3 months from now.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $245). Flying from Gulfport to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 2 airlines flying from Gulfport to Chicago

Discover the top 2 airlines that operate flights from Gulfport to Chicago. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$436FlexibilityNo cancel feeOn-time71%

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