Gulfport

$159+ Cheap flights from Chicago (CHI) to Gulfport (GPT)

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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Jul 8 — Jul 151
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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 July 3, 2025.

Round-trip from

$249
(Delta)

One-way from

$159
(Delta)

Popular in

February

Cheapest in

August

Average price

$548
From Chicago (CHI) to Gulfport Biloxi Regional
One-way flight from Chicago (CHI) to Gulfport Biloxi Regional
Highest demand for flights based on searches. 12% potential increase in price ($61 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 July 3, 2025.

This Delta deal was found by Cheapflights users on 7/2. 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 8/164:25 pmMDW - GPT
1 stop5h 13mDelta
Sat 8/2311:30 amGPT - MDW
1 stop3h 58mDelta
Deal found 7/2$249
This Delta deal was found by Cheapflights users on 7/2. 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 8/163:30 pmORD - GPT
1 stop6h 08mDelta
Sat 8/233:45 pmGPT - ORD
1 stop5h 51mDelta
Deal found 7/2$249
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/146:25 pmORD - GPT
1 stop5h 34mAmerican Airlines
Thu 8/216:30 pmGPT - ORD
1 stop5h 18mAmerican Airlines
Deal found 7/2$250
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 10/316:00 amORD - GPT
1 stop7h 20mUnited Airlines
Sun 11/25:15 pmGPT - ORD
1 stop7h 00mUnited Airlines
Deal found 7/2$388
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Thu 7/175:05 amORD - GPT
3 stops26h 40mMultiple Airlines
Sun 7/2012:55 pmGPT - ORD
2 stops18h 09mMultiple Airlines
Deal found 7/1$493

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 July 3, 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

MDW - GPT

MDWGPT

Chicago Midway

Sat 8/16

4:25 pm-9:38 pm

1 stop5h 13m

Gulfport Biloxi Regional

Sat 8/23

11:30 am-3:28 pm

1 stop3h 58m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

3:30 pm-9:38 pm

1 stop6h 08m

Gulfport Biloxi Regional

Sat 8/23

3:45 pm-9:36 pm

1 stop5h 51m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 8/14

6:25 pm-11:59 pm

1 stop5h 34m

Gulfport Biloxi Regional

Thu 8/21

6:30 pm-11:48 pm

1 stop5h 18m

$250

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

2:10 pm-1:28 pm

2 stops23h 18m

Gulfport Biloxi Regional

Sat 8/23

5:00 pm-10:41 pm

1 stop5h 41m

$393

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 7/17

5:05 am-7:45 am

3 stops26h 40m

Gulfport Biloxi Regional

Sun 7/20

12:55 pm-7:04 am

2 stops18h 09m

$493

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 8/16

4:25 pm-9:38 pm

1 stop5h 13m

$159

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

3:30 pm-9:38 pm

1 stop6h 08m

$159

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 8/28

4:21 pm-10:57 pm

1 stop6h 36m

$190

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 8/10

3:18 pm-7:45 am

2 stops16h 27m

$236

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

8:50 am-9:44 pm

2 stops12h 54m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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.

How much does it cost to fly round-trip from Chicago to Gulfport?

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 July 3, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Gulfport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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!
8.0
Very good
8.0
Very good

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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!
8.0
Very good

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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!
8.0
Very good

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Food

7.3

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 $391, respectively. You may be able to fly from Chicago to Gulfport for 41% less than the average price by searching for these airlines.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $159. Users have also found prices from $190 and $270 on American Airlines and United Airlines, respectively.

  • 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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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$364FlexibilityNo cancel feeOn-time71%
DeltaCheapest$253Average$427FlexibilityNo cancel feeOn-timeN/A

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