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$249+ Cheap flights from Chicago (CHI) to Gulfport (GPT)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Chicago to Gulfport

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

Popular in

February

Cheapest in

August

Average price

$342
From Chicago (CHI) to Gulfport Biloxi Regional
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Highest demand for flights based on searches. 13% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 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 Chicago to Gulfport

Cheapest flights from Chicago to Gulfport
Explore the most affordable flight options available from Chicago to Gulfport. 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 6/10. 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 7/265:35 amORD - GPT
1 stop4h 16mDelta
Sat 8/26:07 amGPT - ORD
1 stop6h 26mDelta
Deal found 6/10$249
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/257:05 amORD - GPT
1 stop5h 03mAmerican Airlines
Fri 8/17:49 pmGPT - ORD
1 stop5h 10mAmerican Airlines
Deal found 6/10$250
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/264:22 pmMDW - GPT
1 stop5h 41mDelta
Sat 8/23:30 pmGPT - MDW
1 stop6h 12mDelta
Deal found 6/11$279
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/99:30 pmORD - GPT
2 stops18h 44mUnited Airlines
Wed 7/165:25 pmGPT - ORD
1 stop6h 50mUnited Airlines
Deal found 6/11$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.
Sun 7/275:05 amORD - GPT
2 stops26h 40mMultiple Airlines
Sun 8/312:55 pmGPT - ORD
1 stop26h 36mMultiple Airlines
Deal found 6/11$443

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Gulfport 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 Chicago to Gulfport that are best for you.

Fly from

Chicago

Fly to

Gulfport

Route

Depart

Return

Price

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 7/26

5:35 am-9:51 am

1 stop4h 16m

Gulfport Biloxi Regional

Sat 8/2

6:07 am-12:33 pm

1 stop6h 26m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 7/25

7:05 am-12:08 pm

1 stop5h 03m

Gulfport Biloxi Regional

Fri 8/1

7:49 pm-12:59 am

1 stop5h 10m

$250

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 7/26

4:22 pm-10:03 pm

1 stop5h 41m

Gulfport Biloxi Regional

Sat 8/2

3:30 pm-9:42 pm

1 stop6h 12m

$279

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 7/9

9:30 pm-4:14 pm

2 stops18h 44m

Gulfport Biloxi Regional

Wed 7/16

5:25 pm-12:15 am

1 stop6h 50m

$396

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 7/27

5:05 am-7:45 am

2 stops26h 40m

Gulfport Biloxi Regional

Sun 8/3

12:55 pm-3:31 pm

1 stop26h 36m

$443

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 7/14

2:26 pm-7:54 pm

1 stop5h 28m

$322

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 6/17

6:00 am-1:21 pm

1 stop7h 21m

$368

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 6/21

5:35 am-9:57 am

1 stop4h 22m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Best time to book a flight from Chicago to Gulfport

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

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $420). 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.

Rainfall in Gulfport by month

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

In terms of precipitation, rainfall in Gulfport ranges from 3.6 - 7.2 inches per month. July is typically the wettest month, when rainfall can reach 7.2 in. October is typically the driest time to visit Gulfport when rainfall is around 3.6 in.

Temperature in Gulfport by month

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

If weather is an important factor for your trip to Gulfport, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

Reviews of airlines servicing Gulfport

Get insights into the airlines that provide service to Gulfport. 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 Gulfport. Reviews last updated June 12, 2025.
Get a feel of what it's like to fly with Delta, United Airlines and American Airlines from Chicago to Gulfport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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

    Gulfport Biloxi Regional (GPT), located 3.1 mi from the city center, is the airport you fly into when you book flights from Chicago to Gulfport. 2 airlines have flights to Biloxi Regional from Chicago on a regular basis. Booking flights from Chicago to Gulfport Biloxi Regional should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

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

    Flying on Delta is currently your cheapest option to Gulfport, with prices starting at $249. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $250 and $396, respectively. You may be able to fly from Chicago to Gulfport for 40% less than the average price by searching for these airlines.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $420). 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.

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Alternative routes for Chicago to Gulfport

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Top 2 airlines flying from Chicago to Gulfport

Discover the top 2 airlines that operate flights from Chicago to Gulfport. 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
American AirlinesCheapest$248Average$377FlexibilityNo cancel feeOn-time71%
DeltaCheapest$253Average$411FlexibilityNo cancel feeOn-timeN/A

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