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Midway

$157+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — MDW
Mar 17 — Mar 241
Tue 3/17
Tue 3/24
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 February 15, 2026.

This Delta deal was found by Cheapflights users on 2/11. 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 3/66:00 pm
GPT
-
MDW
1 stop4h 31m
Delta
Mon 3/912:47 pm
MDW
-
GPT
1 stop4h 24m
Delta
Deal found 2/11$304
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:20 pm
GPT
-
MDW
1 stop25h 07m
Multiple Airlines
Thu 3/57:30 am
MDW
-
GPT
1 stop11h 10m
Multiple Airlines
Deal found 2/14$338
This Delta deal was found by Cheapflights users on 2/14. 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.
Thu 8/276:00 am
GPT
-
MDW
1 stop5h 54m
Delta
Sun 8/301:05 pm
MDW
-
GPT
1 stop4h 12m
Delta
Deal found 2/14$409
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:54 pm
GPT
-
MDW
2 stops25h 13m
Multiple Airlines
Sun 4/129:00 am
MDW
-
GPT
1 stop9h 40m
Multiple Airlines
Deal found 2/14$453
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 3/115:57 pm
GPT
-
MDW
1 stop4h 34m
Delta
Sun 3/1510:45 am
MDW
-
GPT
1 stop6h 26m
Delta
Deal found 2/11$474
This Delta deal was found by Cheapflights users on 2/14. 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.
Thu 7/910:30 am
GPT
-
MDW
1 stop5h 55m
Delta
Mon 7/131:05 pm
MDW
-
GPT
1 stop4h 12m
Delta
Deal found 2/14$547
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Thu 2/197:20 pm
GPT
-
MDW
1 stop19h 06m
Multiple Airlines
Sat 2/219:15 am
MDW
-
GPT
2 stops33h 25m
Multiple Airlines
Deal found 2/12$559
This Delta deal was found by Cheapflights users on 2/12. 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.
Sat 7/183:00 pm
GPT
-
MDW
1 stop6h 45m
Delta
Sun 7/191:05 pm
MDW
-
GPT
1 stop4h 12m
Delta
Deal found 2/12$599
This Delta deal was found by Cheapflights users on 2/12. 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.
Tue 2/246:00 am
GPT
-
MDW
1 stop5h 59m
Delta
Fri 2/2712:45 pm
MDW
-
GPT
1 stop4h 30m
Delta
Deal found 2/12$658
This Delta deal was found by Cheapflights users on 2/14. 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.
Fri 4/105:57 pm
GPT
-
MDW
1 stop4h 34m
Delta
Sun 4/1210:45 am
MDW
-
GPT
1 stop6h 26m
Delta
Deal found 2/14$679

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 February 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$304
(Delta)

One-way from

$157
(Kiwi.com)

Popular in

June

Cheapest in

November
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 ($72 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

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 February 15, 2026.
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

Fri 3/6

6:00 pm-10:31 pm

1 stop4h 31m

Chicago Midway

Mon 3/9

12:47 pm-5:11 pm

1 stop4h 24m

$304

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sun 3/1

7:20 pm-8:27 pm

1 stop25h 07m

Chicago Midway

Thu 3/5

7:30 am-6:40 pm

1 stop11h 10m

$338

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 3/11

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Sun 3/15

10:45 am-5:11 pm

1 stop6h 26m

$474

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 7/18

3:00 pm-9:45 pm

1 stop6h 45m

Chicago Midway

Sun 7/19

1:05 pm-5:17 pm

1 stop4h 12m

$599

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Fri 4/10

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Sun 4/12

10:45 am-5:11 pm

1 stop6h 26m

$679

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Mon 3/2

6:00 pm-10:31 pm

1 stop4h 31m

Chicago Midway

Fri 3/6

10:49 am-5:15 pm

1 stop6h 26m

$699

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 3/12

5:57 pm-10:31 pm

1 stop4h 34m

Chicago Midway

Sat 3/28

4:30 pm-10:15 pm

1 stop5h 45m

$719

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 7/9

6:00 am-12:30 pm

2 stops6h 30m

Chicago Midway

Mon 7/13

5:25 pm-10:07 pm

1 stop4h 42m

$992

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Mon 3/9

6:54 pm-8:54 pm

2 stops26h 00m

$157

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Mon 3/9

5:57 pm-10:31 pm

1 stop4h 34m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 14 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 February.
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 31m. 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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