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$171+ Cheap flights from Gulfport (GPT) to Midway (MDW)

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — MDW
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Cheap flight deals from Gulfport to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Gulfport (GPT) to Midway (MDW). 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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$262
(Kiwi.com)

One-way from

$171
(Kiwi.com)

Popular in

February

Cheapest in

April

Average price

$470
Provider with most accurate pricing for Gulfport Biloxi Regional-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Chicago Midway flights.
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From Gulfport Biloxi Regional to Chicago Midway
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One-way flight from Gulfport Biloxi Regional to Chicago Midway
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Highest demand for flights based on searches. 14% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Gulfport to Midway

Cheapest flights from Gulfport to Midway
Explore the most affordable flight options available from Gulfport to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/197:55 pmGPT - MDW
2 stops19h 17mMultiple Airlines
Thu 10/2310:49 amMDW - GPT
1 stop8h 26mMultiple Airlines
Deal found 9/25$262
This Delta deal was found by Cheapflights users on 9/24. 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.
Wed 10/226:05 pmGPT - MDW
1 stop4h 09mDelta
Wed 10/2910:40 amMDW - GPT
1 stop4h 18mDelta
Deal found 9/24$318
This Delta deal was found by Cheapflights users on 9/22. 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 10/293:45 pmGPT - MDW
1 stop6h 29mDelta
Wed 11/510:40 amMDW - GPT
1 stop4h 18mDelta
Deal found 9/22$339
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:55 pmGPT - MDW
1 stop20h 25mMultiple Airlines
Sun 10/1210:30 amMDW - GPT
2 stops22h 29mMultiple Airlines
Deal found 9/25$353
This Delta deal was found by Cheapflights users on 9/24. 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 12/136:00 amGPT - MDW
2 stops12h 18mDelta
Tue 12/1612:50 pmMDW - GPT
1 stop4h 24mDelta
Deal found 9/24$394
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Fri 10/176:51 pmGPT - MDW
2 stops22h 22mMultiple Airlines
Sun 10/1912:09 pmMDW - GPT
1 stop7h 06mMultiple Airlines
Deal found 9/24$441
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:08 amGPT - MDW
1 stop5h 40mDelta
Tue 9/3012:43 pmMDW - GPT
1 stop4h 36mDelta
Deal found 9/23$589

Cheapflights Fare Finder

 
Customize your flight search to find flights from Gulfport to Midway 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 September 25, 2025.
Use the filters below to find and compare flights from Gulfport to Chicago Midway Airport that are best for you.

Fly from

Gulfport

Fly to

Midway

Route

Depart

Return

Price

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 10/19

7:55 pm-4:20 pm

1 stop20h 25m

Chicago Midway

Thu 10/23

10:49 am-7:15 pm

1 stop8h 26m

$269

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 10/22

6:05 pm-10:14 pm

1 stop4h 09m

Chicago Midway

Wed 10/29

10:40 am-2:58 pm

1 stop4h 18m

$318

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 10/29

3:45 pm-10:14 pm

1 stop6h 29m

Chicago Midway

Wed 11/5

10:40 am-2:58 pm

1 stop4h 18m

$339

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 10/9

7:55 pm-4:20 pm

1 stop20h 25m

Chicago Midway

Sun 10/12

10:30 am-8:59 am

2 stops22h 29m

$353

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 12/13

6:00 am-6:18 pm

2 stops12h 18m

Chicago Midway

Tue 12/16

10:49 am-5:14 pm

1 stop6h 25m

$394

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 11/7

3:45 pm-10:14 pm

1 stop6h 29m

Chicago Midway

Tue 11/11

5:34 pm-10:07 pm

1 stop4h 33m

$433

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 10/17

6:51 pm-5:13 pm

2 stops22h 22m

Chicago Midway

Sun 10/19

12:09 pm-7:15 pm

1 stop7h 06m

$441

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 10/3

6:51 pm-11:41 pm

2 stops28h 50m

$179

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 11/23

7:55 pm-4:52 pm

1 stop20h 57m

$205

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 10/9

7:55 pm-12:24 am

2 stops28h 29m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 15 results
1
2

Compare providers for flights from Gulfport to Midway

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 Gulfport to Midway in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 Gulfport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Gulfport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Gulfport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Gulfport-Chicago Midway Airport 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 Gulfport-Chicago Midway Airport 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 Gulfport to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Gulfport to Chicago Midway Airport (average of $160). Flying from Gulfport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 25, 2025.
Read reviews from past customers who have flown Delta from Gulfport to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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!
Delta
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

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 Gulfport to Midway. 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 Midway?

    Gulfport Biloxi Regional (GPT) is the airport you will fly out of if you book a flight from Gulfport to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Biloxi Regional; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Gulfport airport to Chicago Midway. It is only a 3.1 mi journey to Biloxi Regional (GPT) from Gulfport’s city center.

  • How long is the flight from Gulfport to Chicago Midway Airport?

    Delta can get you from Gulfport to Chicago Midway Airport in just under 4h 09m. Your travel time can differ by up to . The distance from Gulfport to Chicago Midway Airport is about 789 mi.

  • What is the cheapest airline to fly from Gulfport to Chicago Midway Airport round-trip?

    Flying on Delta is currently your cheapest option to Chicago Midway Airport, with prices starting at $116.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Gulfport to Midway 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 Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Gulfport to Chicago Midway Airport (average of $160). Flying from Gulfport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top airline flying from Gulfport to Midway

Discover the top airline that operate flights from Gulfport to Midway. 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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$407FlexibilityNo cancel feeOn-timeN/A

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