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Gulfport

$137+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
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Cheap 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 April 28, 2026.

This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/64:49 pm
ORD
-
GPT
1 stop7h 12m
American Airlines
Tue 6/96:38 pm
GPT
-
ORD
1 stop5h 20m
American Airlines
Deal found 4/28$291
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:34 pm
ORD
-
GPT
1 stop6h 27m
American Airlines
Tue 6/26:38 pm
GPT
-
ORD
1 stop5h 21m
American Airlines
Deal found 4/28$310
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/1010:22 am
ORD
-
GPT
1 stop21h 19m
Multiple Airlines
Thu 5/147:50 pm
GPT
-
ORD
1 stop27h 23m
Multiple Airlines
Deal found 4/24$331
This American Airlines deal was found by Cheapflights users on 4/25. 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 5/116:41 pm
ORD
-
GPT
1 stop5h 17m
American Airlines
Sat 5/166:09 pm
GPT
-
ORD
1 stop5h 45m
American Airlines
Deal found 4/25$334
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MDW
-
GPT
1 stop7h 05m
Delta
Fri 7/316:00 pm
GPT
-
MDW
1 stop4h 15m
Delta
Deal found 4/27$335
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/911:23 am
ORD
-
GPT
1 stop5h 48m
Delta
Sat 6/133:00 pm
GPT
-
ORD
1 stop5h 59m
Delta
Deal found 4/27$335
This Delta deal was found by Cheapflights users on 4/24. 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 5/95:29 pm
MDW
-
GPT
1 stop4h 22m
Delta
Wed 5/136:32 am
GPT
-
MDW
1 stop5h 24m
Delta
Deal found 4/24$339
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:55 am
ORD
-
GPT
2 stops7h 24m
American Airlines
Sat 5/165:03 pm
GPT
-
ORD
1 stop6h 45m
American Airlines
Deal found 4/27$344
This American Airlines deal was found by Cheapflights users on 4/24. 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 5/85:00 am
ORD
-
GPT
1 stop5h 33m
American Airlines
Tue 5/195:03 pm
GPT
-
ORD
1 stop6h 45m
American Airlines
Deal found 4/24$354
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/85:00 am
ORD
-
GPT
1 stop5h 33m
American Airlines
Tue 5/125:03 pm
GPT
-
ORD
1 stop6h 45m
American Airlines
Deal found 4/23$359
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 6/2512:58 pm
ORD
-
GPT
1 stop18h 43m
Multiple Airlines
Mon 6/295:31 pm
GPT
-
ORD
2 stops26h 22m
Multiple Airlines
Deal found 4/27$362
This Delta deal was found by Cheapflights users on 4/28. 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 5/67:10 am
ORD
-
GPT
1 stop6h 44m
Delta
Tue 5/121:55 pm
GPT
-
ORD
1 stop6h 31m
Delta
Deal found 4/28$365

Find 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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(American Airlines)

One-way from

$137
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$409
Provider with most accurate pricing for Chicago (CHI)-Gulfport Biloxi Regional flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Gulfport Biloxi Regional flights.
Search Deals
From Chicago (CHI) to Gulfport Biloxi Regional
Search Deals
One-way flight from Chicago (CHI) to Gulfport Biloxi Regional
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 28, 2026.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 5/9

9:10 am-2:04 pm

1 stop4h 54m

Gulfport Biloxi Regional

Tue 5/19

6:02 pm-10:27 pm

1 stop4h 25m

$334

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 5/9

5:29 pm-9:51 pm

1 stop4h 22m

Gulfport Biloxi Regional

Wed 5/13

6:32 am-11:56 am

1 stop5h 24m

$339

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 5/8

5:00 am-10:33 am

1 stop5h 33m

Gulfport Biloxi Regional

Tue 5/12

5:03 pm-11:48 pm

1 stop6h 45m

$359

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 5/11

5:10 pm-9:51 pm

1 stop4h 41m

Gulfport Biloxi Regional

Sat 5/16

3:00 pm-9:09 pm

1 stop6h 09m

$389

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 5/3

2:05 pm-7:53 pm

1 stop5h 48m

Gulfport Biloxi Regional

Sun 5/10

4:55 pm-12:45 am

1 stop7h 50m

$414

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 5/8

12:53 pm-5:14 pm

1 stop4h 21m

Gulfport Biloxi Regional

Thu 5/14

1:55 pm-9:09 pm

1 stop7h 14m

$439

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sun 5/10

6:00 am-7:10 pm

2 stops13h 10m

Gulfport Biloxi Regional

Thu 5/14

7:50 pm-3:57 pm

1 stop20h 07m

$463

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 6/15

6:35 am-1:07 pm

1 stop6h 32m

Gulfport Biloxi Regional

Fri 6/19

5:56 pm-11:59 pm

1 stop6h 03m

$489

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 5/2

7:10 am-2:06 pm

1 stop6h 56m

Gulfport Biloxi Regional

Sun 5/3

2:40 pm-9:25 pm

1 stop6h 45m

$495

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 5/8

5:10 pm-9:51 pm

1 stop4h 41m

Gulfport Biloxi Regional

Tue 5/12

6:32 am-11:56 am

1 stop5h 24m

$499

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 38 resultsSorted by cheapest first
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4

Compare providers for flights from Chicago to Gulfport

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 Chicago to Gulfport in April.
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 Chicago-Gulfport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Gulfport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Gulfport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Gulfport 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 Chicago-Gulfport 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 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, January is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $248). Flying from Chicago to Gulfport in March is currently the most expensive (average of $373). 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?

How often are flights from Chicago to Gulfport delayed?

About 50% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 127 minutes.

What is the most punctual flight time for Chicago to Gulfport flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Gulfport flights?

Over the last year, Sun Country Air have had the lowest number of delays on this route, with just 56% of flights being delayed.

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 April 28, 2026.
Peruse reviews from past customers who have flown with Delta 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.
Delta
7.9
Good
8,467 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Crew

8.5

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
8,467 reviews
Delta
7.9
Good
8,467 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Crew

8.5

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
7.1
Good
11,677 reviews
Delta
7.9
Good
8,467 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Crew

8.5

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 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.

  • How long is the flight from Chicago to Gulfport?

    Delta, American Airlines, and United Airlines can get you from Chicago to Gulfport in just under 4h 54m. Your travel time can differ by up to 54m. The distance from Chicago to Gulfport is about 802 mi. This flight may include one or multiple stops.

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

    Flying on American Airlines is currently your cheapest option to Gulfport, with prices starting at $248. Another option worth looking into is Delta, starting at $248 round trip. You may be able to fly from Chicago to Gulfport for 35% 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, January is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $248). Flying from Chicago to Gulfport in March is currently the most expensive (average of $373). 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
Ocean Springs
D'Iberville

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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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$323FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$428FlexibilityNo cancel feeOn-timeN/A

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