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$205+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$249
(Delta)

One-way from

$205
(Delta)

Popular in

February

Cheapest in

April

Average price

$330
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. 19% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/12. 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 7/236:07 amGPT - MDW
1 stop5h 51mDelta
Sat 7/264:22 pmMDW - GPT
1 stop5h 41mDelta
Deal found 6/12$249
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/96:36 pmGPT - ORD
1 stop5h 21mAmerican Airlines
Tue 7/151:23 pmORD - GPT
1 stop5h 48mAmerican Airlines
Deal found 6/12$249
This Delta deal was found by Cheapflights users on 6/9. 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 7/256:00 pmGPT - ORD
1 stop6h 09mDelta
Sun 7/277:00 amORD - GPT
1 stop6h 07mDelta
Deal found 6/9$344
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 7/265:25 pmGPT - ORD
1 stop5h 47mUnited Airlines
Wed 7/309:30 pmORD - GPT
2 stops18h 44mUnited Airlines
Deal found 6/12$396
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/275:37 pmGPT - ORD
1 stop27h 42mMultiple Airlines
Sun 6/299:55 amORD - GPT
2 stops21h 50mMultiple Airlines
Deal found 6/11$466

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 June 12, 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 - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 7/23

6:07 am-11:58 am

1 stop5h 51m

Chicago Midway

Sat 7/26

4:22 pm-10:03 pm

1 stop5h 41m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 7/9

6:36 pm-11:57 pm

1 stop5h 21m

Chicago O'Hare Intl

Tue 7/15

1:23 pm-7:11 pm

1 stop5h 48m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 7/25

6:00 pm-12:09 am

1 stop6h 09m

Chicago O'Hare Intl

Sun 7/27

7:00 am-1:07 pm

1 stop6h 07m

$344

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 7/26

5:25 pm-11:12 pm

1 stop5h 47m

Chicago O'Hare Intl

Wed 7/30

9:30 pm-4:14 pm

2 stops18h 44m

$396

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 6/27

5:37 pm-9:19 pm

1 stop27h 42m

Chicago O'Hare Intl

Sun 6/29

9:55 am-7:45 am

2 stops21h 50m

$466

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 8/29

5:00 pm-9:49 pm

1 stop4h 49m

$205

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sun 6/29

12:55 pm-3:33 pm

2 stops26h 38m

$246

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sun 6/29

7:43 pm-12:59 am

1 stop5h 16m

$251

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 8/29

5:00 pm-10:37 pm

1 stop5h 37m

$270

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 6/29

12:55 pm-2:03 pm

2 stops25h 08m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 11 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.

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 June 12, 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 June 12, 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
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

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!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

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
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

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.

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

    According to our current data, Delta ($249), American Airlines ($249), and United Airlines ($396) offers the cheapest pricing from Gulfport to Chicago. These flights start at 38% 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 Delta ($205), American Airlines ($251), and United Airlines ($446).

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$428FlexibilityNo cancel feeOn-time71%

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