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Midway

$179+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — MDW
Apr 29 — May 61
Wed 4/29
Wed 5/6
1 adult, Economy
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Cheap 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 March 30, 2026.

This Delta deal was found by Cheapflights users on 3/29. 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 5/26:00 am
GPT
-
MDW
1 stop4h 14m
Delta
Sat 5/96:23 am
MDW
-
GPT
1 stop7h 16m
Delta
Deal found 3/29$291
This Delta deal was found by Cheapflights users on 3/29. 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 4/305:55 pm
GPT
-
MDW
1 stop4h 33m
Delta
Sat 5/25:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Deal found 3/29$310
This Delta deal was found by Cheapflights users on 3/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:55 pm
GPT
-
MDW
1 stop4h 33m
Delta
Wed 4/2910:41 am
MDW
-
GPT
1 stop6h 28m
Delta
Deal found 3/25$354
This Delta deal was found by Cheapflights users on 3/26. 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 4/105:57 pm
GPT
-
MDW
1 stop4h 34m
Delta
Tue 4/145:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Deal found 3/26$369
This Delta deal was found by Cheapflights users on 3/27. 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.
Wed 8/1210:30 am
GPT
-
MDW
1 stop5h 57m
Delta
Mon 8/175:25 pm
MDW
-
GPT
1 stop4h 41m
Delta
Deal found 3/27$384
This Delta deal was found by Cheapflights users on 3/30. 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 4/145:55 pm
GPT
-
MDW
1 stop4h 33m
Delta
Sat 4/185:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Deal found 3/30$389
This Delta deal was found by Cheapflights users on 3/27. 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.
Thu 4/26:00 am
GPT
-
MDW
1 stop6h 02m
Delta
Sun 4/510:45 am
MDW
-
GPT
1 stop6h 26m
Delta
Deal found 3/27$414
This Delta deal was found by Cheapflights users on 3/30. 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 4/305:55 pm
GPT
-
MDW
1 stop4h 33m
Delta
Mon 5/45:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Deal found 3/30$423
This Delta deal was found by Cheapflights users on 3/29. 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 5/26:00 am
GPT
-
MDW
1 stop4h 14m
Delta
Sun 5/35:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Deal found 3/29$465
This Delta deal was found by Cheapflights users on 3/26. 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 7/86:00 pm
GPT
-
MDW
1 stop4h 15m
Delta
Mon 7/135:10 pm
MDW
-
GPT
1 stop5h 04m
Delta
Deal found 3/26$475
This Delta deal was found by Cheapflights users on 3/29. 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 4/245:55 pm
GPT
-
MDW
1 stop4h 33m
Delta
Sun 4/265:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Deal found 3/29$484
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/27:20 pm
GPT
-
MDW
2 stops24h 47m
Multiple Airlines
Sun 4/55:05 am
MDW
-
GPT
1 stop13h 35m
Multiple Airlines
Deal found 3/27$504

Find 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 March 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(Delta)

One-way from

$179
(Delta)

Popular in

June

Cheapest in

November

Average price

$338
Provider with most accurate pricing for Gulfport Biloxi Regional-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Chicago Midway flights.
Search Deals
From Gulfport Biloxi Regional to Chicago Midway
Search Deals
One-way flight from Gulfport Biloxi Regional to Chicago Midway
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 30, 2026.
Use the filters below to find and compare flights from Gulfport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 5/2

6:00 am-10:14 am

1 stop4h 14m

Chicago Midway

Sat 5/9

6:23 am-1:39 pm

1 stop7h 16m

$291

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 4/22

5:55 pm-10:28 pm

1 stop4h 33m

Chicago Midway

Wed 4/29

10:41 am-5:09 pm

1 stop6h 28m

$354

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 8/12

10:30 am-4:27 pm

1 stop5h 57m

Chicago Midway

Mon 8/17

5:25 pm-10:06 pm

1 stop4h 41m

$384

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 4/30

5:55 pm-10:28 pm

1 stop4h 33m

Chicago Midway

Mon 5/4

5:21 pm-10:13 pm

1 stop4h 52m

$423

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 4/24

5:55 pm-10:28 pm

1 stop4h 33m

Chicago Midway

Sun 4/26

5:21 pm-10:13 pm

1 stop4h 52m

$484

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

6:00 am-11:54 am

1 stop5h 54m

Chicago Midway

Sun 8/30

5:25 pm-10:06 pm

1 stop4h 41m

$539

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 5/15

1:55 pm-9:09 pm

1 stop7h 14m

Chicago Midway

Tue 5/19

6:23 am-1:09 pm

1 stop6h 46m

$739
Quickest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Mon 4/13

5:55 pm-10:28 pm

1 stop4h 33m

Chicago Midway

Fri 4/17

12:52 pm-5:08 pm

1 stop4h 16m

$775

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 6/4

1:55 pm-9:09 pm

1 stop7h 14m

Chicago Midway

Sun 6/7

5:11 pm-10:17 pm

1 stop5h 06m

$778

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 4/9

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Sun 4/12

10:45 am-5:11 pm

1 stop6h 26m

$879

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 12 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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, November is the cheapest month in which you can book a flight from Gulfport to Chicago Midway Airport (average of $105). Flying from Gulfport to Chicago Midway Airport in January is currently the most expensive (average of $251). 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.

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 0 airlines have 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 14m. Your travel time can differ by up to . The distance from Gulfport to Chicago Midway Airport is about 789 mi.

  • 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, November is the cheapest month in which you can book a flight from Gulfport to Chicago Midway Airport (average of $105). Flying from Gulfport to Chicago Midway Airport in January is currently the most expensive (average of $251). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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