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$135+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:54 pm
GPT
-
ORD
2 stops28h 53m
Multiple Airlines
Thu 3/511:55 am
ORD
-
GPT
1 stop6h 45m
Multiple Airlines
Deal found 1/27$243
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 3/227:20 pm
GPT
-
ORD
2 stops16h 01m
Multiple Airlines
Wed 4/14:21 pm
ORD
-
GPT
1 stop26h 19m
Multiple Airlines
Deal found 1/28$251
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 3/227:20 pm
GPT
-
ORD
1 stop20h 05m
Multiple Airlines
Thu 4/29:30 am
ORD
-
GPT
1 stop9h 10m
Multiple Airlines
Deal found 1/28$263
This Delta deal was found by Cheapflights users on 1/28. 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 3/185:57 pm
GPT
-
MDW
1 stop4h 34m
Delta
Tue 3/3112:47 pm
MDW
-
GPT
1 stop4h 24m
Delta
Deal found 1/28$269
This Delta deal was found by Cheapflights users on 1/28. 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 3/185:57 pm
GPT
-
ORD
1 stop5h 57m
Delta
Tue 3/315:59 pm
ORD
-
GPT
1 stop4h 16m
Delta
Deal found 1/28$269
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 3/197:20 pm
GPT
-
ORD
2 stops37h 50m
Multiple Airlines
Wed 4/14:21 pm
ORD
-
GPT
1 stop26h 19m
Multiple Airlines
Deal found 1/28$272
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 3/227:20 pm
GPT
-
MDW
1 stop19h 01m
Multiple Airlines
Thu 4/29:20 am
MDW
-
GPT
1 stop9h 20m
Multiple Airlines
Deal found 1/28$278
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 2/136:00 pm
GPT
-
ORD
1 stop5h 56m
Delta
Mon 2/169:48 am
ORD
-
GPT
1 stop7h 27m
Delta
Deal found 1/28$279
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 3/213:00 pm
GPT
-
ORD
1 stop5h 02m
Delta
Wed 4/19:40 am
ORD
-
GPT
1 stop4h 20m
Delta
Deal found 1/28$294
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 3/197:20 pm
GPT
-
ORD
2 stops37h 50m
Multiple Airlines
Thu 4/29:30 am
ORD
-
GPT
1 stop9h 10m
Multiple Airlines
Deal found 1/28$299
This Delta deal was found by Cheapflights users on 1/28. 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.
Sun 3/225:57 pm
GPT
-
ORD
1 stop5h 57m
Delta
Tue 3/3111:10 am
ORD
-
GPT
1 stop6h 01m
Delta
Deal found 1/28$304
This Delta deal was found by Cheapflights users on 1/28. 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 3/185:57 pm
GPT
-
MDW
1 stop4h 34m
Delta
Wed 4/19:30 am
MDW
-
GPT
2 stops12h 45m
Delta
Deal found 1/28$308

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$243
(Kiwi.com)

One-way from

$135
(Kiwi.com)

Popular in

February

Cheapest in

November
Provider with most accurate pricing for Gulfport Biloxi Regional-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Chicago (CHI) flights.
Search Deals
From Gulfport Biloxi Regional to Chicago (CHI)
Search Deals
One-way flight from Gulfport Biloxi Regional to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($140 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($31 potential savings vs. average RT price).
Search Deals

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 January 29, 2026.
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

Mon 3/2

6:54 pm-11:47 pm

2 stops28h 53m

Chicago O'Hare Intl

Thu 3/5

11:55 am-6:40 pm

1 stop6h 45m

$243

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Tue 3/24

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Wed 4/1

10:45 am-5:11 pm

1 stop6h 26m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 2/19

7:35 pm-12:55 am

1 stop5h 20m

Chicago O'Hare Intl

Sun 2/22

5:00 am-10:13 am

1 stop5h 13m

$269

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 3/18

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Wed 4/1

10:45 am-5:11 pm

1 stop6h 26m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 3/18

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Mon 3/30

5:59 pm-10:15 pm

1 stop4h 16m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 5/1

2:40 pm-8:16 pm

1 stop5h 36m

Chicago O'Hare Intl

Sat 5/9

9:30 am-1:34 pm

1 stop4h 04m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 3/20

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Mon 3/30

5:59 pm-10:15 pm

1 stop4h 16m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 3/18

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Tue 3/31

5:59 pm-10:15 pm

1 stop4h 16m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 3/23

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Wed 4/1

5:59 pm-10:15 pm

1 stop4h 16m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 3/24

5:57 pm-11:54 pm

1 stop5h 57m

Chicago O'Hare Intl

Mon 3/30

5:59 pm-10:15 pm

1 stop4h 16m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 34 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Gulfport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Gulfport-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, February is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $53). Flying from Gulfport to Chicago in December is currently the most expensive (average of $159). 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 January 29, 2026.
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
8,128 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

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
8,128 reviews
Delta
7.9
Good
8,128 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

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
11,205 reviews
Delta
7.9
Good
8,128 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Overall

7.9

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 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 4h 34m. Delta provides one of the quickest options available for as low as $269. There are 789 mi between Gulfport and Chicago.

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

    According to our current data, American Airlines ($248), and Delta ($319) offers the cheapest pricing from Gulfport to Chicago. These flights start at 31% 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, February is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $53). Flying from Gulfport to Chicago in December is currently the most expensive (average of $159). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Gulfport to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$436FlexibilityNo cancel feeOn-time71%
DeltaCheapest$319Average$553FlexibilityNo cancel feeOn-timeN/A

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