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$210+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$249
(Delta)

One-way from

$210
(Delta)

Popular in

February

Cheapest in

April

Average price

$368
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. 15% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 8/233:45 pmGPT - MDW
1 stop5h 27mDelta
Tue 8/264:25 pmMDW - GPT
1 stop5h 13mDelta
Deal found 7/28$249

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 July 29, 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

Sat 8/23

3:45 pm-9:12 pm

1 stop5h 27m

Chicago Midway

Tue 8/26

4:25 pm-9:38 pm

1 stop5h 13m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 10/2

6:08 am-11:48 am

1 stop5h 40m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 29, 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
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

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
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

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.

  • 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 $249.

  • 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
Valparaiso
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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$407FlexibilityNo cancel feeOn-timeN/A

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