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Gulfport

$163+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Jul 17 — Jul 241
Fri 7/17
Fri 7/24
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 June 17, 2026.

This American Airlines deal was found by Cheapflights users on 6/13. 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 7/286:47 pm
ORD
-
GPT
1 stop5h 09m
American Airlines
Sat 8/17:04 am
GPT
-
ORD
1 stop7h 16m
American Airlines
Deal found 6/13$286
This Delta deal was found by Cheapflights users on 6/15. 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 7/146:00 am
MDW
-
GPT
1 stop7h 05m
Delta
Sat 7/184:00 pm
GPT
-
MDW
1 stop6h 15m
Delta
Deal found 6/15$295
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/144:45 pm
ORD
-
GPT
1 stop7h 11m
American Airlines
Sat 7/186:35 pm
GPT
-
ORD
1 stop5h 26m
American Airlines
Deal found 6/16$295
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.
Thu 12/105:30 am
ORD
-
GPT
1 stop4h 09m
Delta
Tue 12/152:15 pm
GPT
-
ORD
2 stops8h 20m
Delta
Deal found 6/12$300
This American Airlines deal was found by Cheapflights users on 6/15. 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 8/76:49 am
ORD
-
GPT
1 stop6h 28m
American Airlines
Mon 8/106:34 pm
GPT
-
ORD
1 stop5h 44m
American Airlines
Deal found 6/15$309
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/215:00 am
ORD
-
GPT
1 stop5h 55m
American Airlines
Mon 7/276:35 pm
GPT
-
ORD
1 stop5h 26m
American Airlines
Deal found 6/14$320
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:03 pm
ORD
-
GPT
2 stops29h 02m
Multiple Airlines
Sun 11/17:45 pm
GPT
-
ORD
1 stop12h 36m
Multiple Airlines
Deal found 6/12$329
This Delta deal was found by Cheapflights users on 6/15. 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 8/75:10 pm
MDW
-
GPT
1 stop5h 11m
Delta
Mon 8/106:00 pm
GPT
-
MDW
1 stop4h 36m
Delta
Deal found 6/15$334
This American Airlines deal was found by Cheapflights users on 6/17. 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 7/136:47 pm
ORD
-
GPT
1 stop5h 09m
American Airlines
Mon 7/206:35 pm
GPT
-
ORD
1 stop5h 26m
American Airlines
Deal found 6/17$334
This Delta deal was found by Cheapflights users on 6/14. 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 12/1212:30 pm
MDW
-
GPT
2 stops9h 37m
Delta
Fri 12/186:00 pm
GPT
-
MDW
1 stop4h 10m
Delta
Deal found 6/14$339
This United Airlines deal was found by Cheapflights users on 6/15. 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 11/142:15 pm
ORD
-
GPT
1 stop7h 12m
United Airlines
Tue 11/175:15 pm
GPT
-
ORD
1 stop5h 21m
United Airlines
Deal found 6/15$361
This Delta deal was found by Cheapflights users on 6/13. 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.
Thu 9/176:40 am
ORD
-
GPT
1 stop6h 19m
Delta
Tue 9/226:26 am
GPT
-
ORD
2 stops10h 04m
Delta
Deal found 6/13$369

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 June 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$286
(American Airlines)

One-way from

$163
(Trip.com)

Popular in

April

Cheapest in

August

Average price

$358
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. 18% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 17, 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

MDW - GPT

MDWGPT

Chicago Midway

Tue 7/21

5:10 pm-10:14 pm

1 stop5h 04m

Gulfport Biloxi Regional

Mon 7/27

5:57 pm-10:15 pm

1 stop4h 18m

$295
Quickest round-trip

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 12/10

5:30 am-9:39 am

1 stop4h 09m

Gulfport Biloxi Regional

Tue 12/15

2:15 pm-6:32 pm

1 stop4h 17m

$295

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 11/14

7:45 am-1:26 pm

1 stop5h 41m

Gulfport Biloxi Regional

Tue 11/17

5:15 pm-10:36 pm

1 stop5h 21m

$361

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sun 9/13

5:25 pm-10:06 pm

1 stop4h 41m

Gulfport Biloxi Regional

Sun 9/20

5:59 pm-10:25 pm

1 stop4h 26m

$378

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 8/14

9:54 am-5:15 pm

1 stop7h 21m

Gulfport Biloxi Regional

Sun 8/16

6:30 am-2:09 pm

1 stop7h 39m

$378

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 7/4

8:36 am-8:41 pm

2 stops12h 05m

Gulfport Biloxi Regional

Tue 7/7

1:51 pm-6:45 pm

1 stop4h 54m

$380

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 11/30

5:30 am-9:39 am

1 stop4h 09m

Gulfport Biloxi Regional

Thu 12/3

6:00 am-12:06 pm

1 stop6h 06m

$391

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 10/8

5:55 pm-10:07 pm

1 stop4h 12m

Gulfport Biloxi Regional

Mon 10/12

2:15 pm-6:32 pm

1 stop4h 17m

$403

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 9/17

6:00 am-5:14 pm

2 stops11h 14m

Gulfport Biloxi Regional

Tue 9/22

10:06 am-8:26 pm

2 stops10h 20m

$429

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 7/16

6:35 am-1:05 pm

1 stop6h 30m

Gulfport Biloxi Regional

Sun 7/19

5:57 pm-11:53 pm

1 stop5h 56m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 26 resultsSorted by cheapest first
1
2
3

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 June.
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 May is currently the most expensive (average of $398). 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 56% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 121 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 64% 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 June 17, 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
7.8
Good
8,406 reviews

Comfort

7.8

Boarding

8.1

Overall

7.8

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,406 reviews
Delta
7.8
Good
8,406 reviews

Comfort

7.8

Boarding

8.1

Overall

7.8

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,670 reviews
Delta
7.8
Good
8,406 reviews

Comfort

7.8

Boarding

8.1

Overall

7.8

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 and United Airlines can get you from Chicago to Gulfport in just under 5h 04m. Your travel time can differ by up to 37m. The distance from Chicago to Gulfport is about 789 mi. This flight may include one or multiple stops.

  • 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 $268. Another option worth looking into is American Airlines, starting at $283 round trip. You may be able to fly from Chicago to Gulfport for 34% 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 May is currently the most expensive (average of $398). 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
D'Iberville
Ocean Springs

Browse thousands of different options on Cheapflights for your next trip

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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 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$462FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$474FlexibilityNo cancel feeOn-time71%

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