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$119+ Cheap flights from Midway (MDW) 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GPT
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Gulfport

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 September 11, 2025.

Round-trip from

$259
(Delta)

One-way from

$119
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$393
From Chicago Midway to Gulfport Biloxi Regional
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One-way flight from Chicago Midway to Gulfport Biloxi Regional
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Highest demand for flights based on searches. 14% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 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 Midway to Gulfport

Cheapest flights from Midway to Gulfport
Explore the most affordable flight options available from Midway to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 9/2612:43 pmMDW - GPT
1 stop4h 36mDelta
Tue 9/306:08 amGPT - MDW
1 stop5h 40mDelta
Deal found 9/11$259
This Delta deal was found by Cheapflights users on 9/10. 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 9/274:25 pmMDW - GPT
1 stop5h 14mDelta
Wed 10/16:08 amGPT - MDW
1 stop5h 40mDelta
Deal found 9/10$284
This Delta deal was found by Cheapflights users on 9/9. 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 9/3010:35 amMDW - GPT
1 stop6h 44mDelta
Mon 10/66:05 pmGPT - MDW
1 stop4h 09mDelta
Deal found 9/9$328
This Delta deal was found by Cheapflights users on 9/9. 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 11/224:28 pmMDW - GPT
1 stop5h 39mDelta
Tue 11/256:03 pmGPT - MDW
1 stop5h 29mDelta
Deal found 9/9$463
This Delta deal was found by Cheapflights users on 9/11. 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 11/2012:47 pmMDW - GPT
1 stop4h 26mDelta
Sun 11/236:03 pmGPT - MDW
1 stop5h 29mDelta
Deal found 9/11$474
This Delta deal was found by Cheapflights users on 9/9. 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 10/910:35 amMDW - GPT
1 stop6h 45mDelta
Thu 10/166:05 pmGPT - MDW
1 stop4h 09mDelta
Deal found 9/9$512
This Delta deal was found by Cheapflights users on 9/8. 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.
Mon 10/610:35 amMDW - GPT
1 stop6h 45mDelta
Mon 10/136:05 pmGPT - MDW
1 stop4h 09mDelta
Deal found 9/8$519
This Delta deal was found by Cheapflights users on 9/10. 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 9/2412:43 pmMDW - GPT
1 stop4h 36mDelta
Sat 9/273:45 pmGPT - MDW
1 stop5h 25mDelta
Deal found 9/10$554
This Delta deal was found by Cheapflights users on 9/10. 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 10/310:35 amMDW - GPT
1 stop6h 44mDelta
Sat 10/43:45 pmGPT - MDW
1 stop5h 25mDelta
Deal found 9/10$579

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Gulfport that are best for you.

Fly from

Midway

Fly to

Gulfport

Route

Depart

Return

Price

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Wed 10/1

6:08 am-11:48 am

1 stop5h 40m

$284

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 9/30

10:35 am-5:19 pm

1 stop6h 44m

Gulfport Biloxi Regional

Mon 10/6

6:05 pm-10:14 pm

1 stop4h 09m

$328

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 11/22

4:28 pm-10:07 pm

1 stop5h 39m

Gulfport Biloxi Regional

Tue 11/25

6:03 pm-11:32 pm

1 stop5h 29m

$463

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 11/20

12:47 pm-5:13 pm

1 stop4h 26m

Gulfport Biloxi Regional

Sun 11/23

6:03 pm-11:32 pm

1 stop5h 29m

$474

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 10/9

10:35 am-5:20 pm

1 stop6h 45m

Gulfport Biloxi Regional

Thu 10/16

6:05 pm-10:14 pm

1 stop4h 09m

$512

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 10/6

10:35 am-5:20 pm

1 stop6h 45m

Gulfport Biloxi Regional

Mon 10/13

6:05 pm-10:14 pm

1 stop4h 09m

$519

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sun 11/2

10:12 am-7:15 pm

1 stop9h 03m

$119

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 10/14

5:04 pm-9:50 pm

1 stop4h 46m

$245

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 11/22

6:00 am-8:59 am

3 stops50h 59m

$250

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 9/26

10:35 am-5:19 pm

1 stop6h 44m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 13 results
1
2

Best time to book a flight from Midway to Gulfport

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

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Gulfport (average of $318). Flying from Chicago Midway Airport to Gulfport in March is currently the most expensive (average of $417). 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 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 September 11, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Gulfport, such as Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

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 Midway 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 Midway?

    Most people fly into Gulfport Biloxi Regional (GPT) if they book a flight to Gulfport from Chicago Midway. On average, Biloxi Regional has 0 inbound flights from Chicago Midway per day from 1 airline. Gulfport Biloxi Regional is conveniently located just 3.1 mi from Gulfport’s city center.

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

    Airlines like Delta fly from Chicago Midway Airport to Gulfport in about 5h 14m. The time it takes to get you to your destination can typically vary by up to . The distance from Chicago Midway Airport to Gulfport is about 789 mi.

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

    Delta, at $253, was found to be the cheapest airline from Chicago Midway Airport to Gulfport..

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Gulfport (average of $318). Flying from Chicago Midway Airport to Gulfport in March is currently the most expensive (average of $417). 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Gulfport

Discover the top airline that operate flights from Midway 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$253Average$436FlexibilityNo cancel feeOn-timeN/A

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