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$219+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$219
(American Airlines)

Popular in

February

Cheapest in

April

Average price

$527
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. 16% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 6/26:21 pmGPT - ORD
1 stop5h 50mAmerican Airlines
Wed 6/115:00 amORD - GPT
1 stop5h 20mAmerican Airlines
Deal found 4/30$249
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/96:07 amGPT - MDW
1 stop5h 46mDelta
Tue 7/156:00 amMDW - GPT
1 stop7h 15mDelta
Deal found 4/29$279
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/144:55 pmGPT - ORD
1 stop7h 20mUnited Airlines
Sun 5/185:15 amORD - GPT
1 stop8h 11mUnited Airlines
Deal found 4/29$327
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/55:37 pmGPT - ORD
2 stops15h 47mMultiple Airlines
Wed 5/712:41 pmORD - GPT
2 stops29h 08mMultiple Airlines
Deal found 4/29$590
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/56:02 pmGPT - ORD
1 stop5h 57mDelta
Wed 5/73:57 pmORD - GPT
1 stop6h 08mDelta
Deal found 4/29$797

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 May 1, 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

Mon 6/2

6:21 pm-12:11 am

1 stop5h 50m

Chicago O'Hare Intl

Wed 6/11

5:00 am-10:20 am

1 stop5h 20m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 7/9

6:07 am-11:53 am

1 stop5h 46m

Chicago Midway

Tue 7/15

6:00 am-1:15 pm

1 stop7h 15m

$279

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 5/14

4:55 pm-12:15 am

1 stop7h 20m

Chicago O'Hare Intl

Sun 5/18

5:15 am-1:26 pm

1 stop8h 11m

$327

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 7/9

6:07 am-4:49 pm

2 stops10h 42m

Chicago O'Hare Intl

Tue 7/15

6:00 am-1:15 pm

2 stops7h 15m

$1,014

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 6/23

7:43 pm-12:59 am

1 stop5h 16m

$219

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 5/15

4:55 pm-12:15 am

1 stop7h 20m

$286

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 5/11

6:05 am-11:53 am

1 stop5h 48m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 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, 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.

What is the cheapest time of day to fly from GPT to CHI?

Find hourly flight availability from Gulfport to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 31% on flights from Gulfport to Chicago by exploring options for tickets in the evening.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Read through reviews of airlines operating flights from Gulfport to Chicago, such as Delta, United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    According to our current data, American Airlines ($249), Delta ($279), and United Airlines ($327) offers the cheapest pricing from Gulfport to Chicago. These flights start at 41% lower than the current average price 3 months from now.

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

    The cheapest airlines for a one-way flight from Gulfport to Chicago are American Airlines ($219), United Airlines ($286), and Delta ($375).

  • 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 Gulfport?

Book flights to Gulfport if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$281Average$415FlexibilityNo cancel feeOn-time71%

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