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$122+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(Kiwi.com)

One-way from

$122
(Kiwi.com)

Popular in

February

Cheapest in

April

Average price

$357
Provider with most accurate pricing for Gulfport Biloxi Regional-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Chicago (CHI) flights.
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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 ($72 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 October 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 12/126:51 pmGPT - ORD
2 stops17h 03mMultiple Airlines
Sun 12/148:45 amORD - GPT
1 stop24h 14mMultiple Airlines
Deal found 10/28$209
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 11/255:55 pmGPT - ORD
1 stop15h 52mMultiple Airlines
Wed 11/266:15 pmORD - GPT
1 stop25h 00mMultiple Airlines
Deal found 10/28$230
This Delta deal was found by Cheapflights users on 10/28. 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 12/245:21 pmGPT - MDW
1 stop5h 01mDelta
Sat 12/276:00 amMDW - GPT
1 stop4h 40mDelta
Deal found 10/28$249
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/55:32 pmGPT - ORD
1 stop6h 07mAmerican Airlines
Sun 12/77:10 amORD - GPT
1 stop5h 17mAmerican Airlines
Deal found 10/28$249
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/125:26 pmGPT - ORD
1 stop6h 11mAmerican Airlines
Sun 11/165:00 amORD - GPT
1 stop7h 23mAmerican Airlines
Deal found 10/28$259
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/175:15 pmGPT - ORD
1 stop5h 55mUnited Airlines
Sun 11/236:00 amORD - GPT
1 stop5h 17mUnited Airlines
Deal found 10/28$264
This Delta deal was found by Cheapflights users on 10/27. 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 12/1310:35 amGPT - MDW
1 stop5h 09mDelta
Tue 12/165:39 pmMDW - GPT
1 stop4h 24mDelta
Deal found 10/27$274
This Delta deal was found by Cheapflights users on 10/27. 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 11/266:03 pmGPT - ORD
1 stop5h 59mDelta
Sun 11/305:23 amORD - GPT
1 stop4h 26mDelta
Deal found 10/27$274
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 12/56:51 pmGPT - ORD
2 stops37h 51mMultiple Airlines
Sun 12/712:09 pmORD - GPT
1 stop7h 06mMultiple Airlines
Deal found 10/28$278
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/134:54 pmGPT - ORD
1 stop6h 46mAmerican Airlines
Mon 11/175:40 pmORD - GPT
1 stop5h 04mAmerican Airlines
Deal found 10/29$279
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/35:26 pmGPT - ORD
1 stop6h 11mAmerican Airlines
Mon 11/178:20 amORD - GPT
1 stop5h 00mAmerican Airlines
Deal found 10/27$284
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/176:51 pmGPT - ORD
2 stops24h 47mMultiple Airlines
Sun 11/2311:23 amORD - GPT
1 stop7h 52mMultiple Airlines
Deal found 10/28$286

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 October 29, 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

Fri 12/12

6:51 pm-11:54 am

2 stops17h 03m

Chicago O'Hare Intl

Sun 12/14

8:45 am-8:59 am

1 stop24h 14m

$209

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 11/25

5:55 pm-9:47 am

1 stop15h 52m

Chicago O'Hare Intl

Wed 11/26

6:15 pm-7:15 pm

1 stop25h 00m

$230

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 11/26

6:03 pm-11:40 pm

1 stop5h 37m

Chicago Midway

Sun 11/30

10:47 am-5:13 pm

1 stop6h 26m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 12/12

6:01 pm-11:47 pm

1 stop5h 46m

Chicago Midway

Sun 12/14

5:13 pm-10:03 pm

1 stop4h 50m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 12/24

5:21 pm-10:22 pm

1 stop5h 01m

Chicago Midway

Sat 12/27

6:00 am-10:40 am

1 stop4h 40m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 12/24

5:21 pm-12:02 am

1 stop6h 41m

Chicago O'Hare Intl

Sat 12/27

5:31 pm-9:40 pm

1 stop4h 09m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 11/17

5:15 pm-11:10 pm

1 stop5h 55m

Chicago O'Hare Intl

Sun 11/23

6:00 am-11:17 am

1 stop5h 17m

$264

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 12/13

10:35 am-3:44 pm

1 stop5h 09m

Chicago Midway

Tue 12/16

12:50 pm-5:16 pm

1 stop4h 26m

$274

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 11/26

6:03 pm-12:02 am

1 stop5h 59m

Chicago O'Hare Intl

Sun 11/30

5:23 am-9:49 am

1 stop4h 26m

$274

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 12/5

6:51 pm-8:42 am

2 stops37h 51m

Chicago O'Hare Intl

Sun 12/7

12:09 pm-7:15 pm

1 stop7h 06m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 29 results
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Compare providers for flights from Gulfport to Chicago

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 Gulfport to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Gulfport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Gulfport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Gulfport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Gulfport-Chicago 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 Gulfport-Chicago 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 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, March is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $58). Flying from Gulfport to Chicago in January is currently the most expensive (average of $168). 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 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 October 29, 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
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 5h 37m. Delta provides one of the quickest options available for as low as $249. There are 789 mi between Gulfport and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, March is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $58). Flying from Gulfport to Chicago in January is currently the most expensive (average of $168). 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
Porter
Benton Harbor

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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$480FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$441FlexibilityNo cancel feeOn-time71%

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