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$125+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GPT
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 11/1810:47 amMDW - GPT
1 stop6h 26mDelta
Tue 11/256:03 pmGPT - MDW
1 stop5h 37mDelta
Deal found 10/28$249
This Delta deal was found by Cheapflights users on 10/27. 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.
Sat 12/64:29 pmMDW - GPT
1 stop5h 34mDelta
Sat 12/1310:35 amGPT - MDW
1 stop5h 09mDelta
Deal found 10/27$274
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:06 pmMDW - GPT
2 stops29h 09mMultiple Airlines
Sun 11/167:55 pmGPT - MDW
1 stop12h 37mMultiple Airlines
Deal found 10/28$294
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 12/235:05 pmMDW - GPT
1 stop4h 35mDelta
Fri 12/265:21 pmGPT - MDW
1 stop5h 01mDelta
Deal found 10/27$299
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/115:34 pmMDW - GPT
1 stop4h 33mDelta
Sat 11/1510:35 amGPT - MDW
1 stop5h 08mDelta
Deal found 10/26$314
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Mon 11/245:47 pmMDW - GPT
1 stop23h 28mMultiple Airlines
Mon 12/16:51 pmGPT - MDW
2 stops37h 55mMultiple Airlines
Deal found 10/27$316
This Delta deal was found by Cheapflights users on 10/27. 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 11/2010:47 amMDW - GPT
1 stop6h 26mDelta
Sun 11/236:00 amGPT - MDW
1 stop5h 52mDelta
Deal found 10/27$324
This Delta deal was found by Cheapflights users on 10/26. 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.
Sat 11/110:40 amMDW - GPT
1 stop4h 18mDelta
Sun 11/23:45 pmGPT - MDW
1 stop6h 29mDelta
Deal found 10/26$384
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 11/510:40 amMDW - GPT
1 stop4h 18mDelta
Sun 11/96:03 pmGPT - MDW
1 stop5h 37mDelta
Deal found 10/28$389
This Delta deal was found by Cheapflights users on 10/26. 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 11/285:34 pmMDW - GPT
1 stop4h 33mDelta
Fri 12/56:00 amGPT - MDW
1 stop5h 55mDelta
Deal found 10/26$420

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$125
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$380
Provider with most accurate pricing for Chicago Midway-Gulfport Biloxi Regional flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Gulfport Biloxi Regional flights.
Search Deals
From Chicago Midway to Gulfport Biloxi Regional
Search Deals
One-way flight from Chicago Midway to Gulfport Biloxi Regional
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 28, 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

Tue 11/18

10:47 am-5:13 pm

1 stop6h 26m

Gulfport Biloxi Regional

Tue 11/25

6:03 pm-11:40 pm

1 stop5h 37m

$249

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 11/12

2:06 pm-7:15 pm

2 stops29h 09m

Gulfport Biloxi Regional

Sun 11/16

7:55 pm-8:32 am

1 stop12h 37m

$294

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 12/23

6:00 am-1:26 pm

1 stop7h 26m

Gulfport Biloxi Regional

Fri 12/26

5:21 pm-10:22 pm

1 stop5h 01m

$299

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 11/20

10:47 am-5:13 pm

1 stop6h 26m

Gulfport Biloxi Regional

Sun 11/23

6:00 am-11:52 am

1 stop5h 52m

$299

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 12/5

12:50 pm-5:16 pm

1 stop4h 26m

Gulfport Biloxi Regional

Sun 12/7

6:01 pm-11:47 pm

1 stop5h 46m

$384

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 11/1

10:40 am-2:58 pm

1 stop4h 18m

Gulfport Biloxi Regional

Sun 11/2

3:45 pm-10:14 pm

1 stop6h 29m

$384

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 11/5

10:40 am-2:58 pm

1 stop4h 18m

Gulfport Biloxi Regional

Sun 11/9

6:03 pm-11:40 pm

1 stop5h 37m

$389

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 11/28

5:34 pm-10:07 pm

1 stop4h 33m

Gulfport Biloxi Regional

Fri 12/5

6:00 am-11:55 am

1 stop5h 55m

$420

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 11/26

5:30 pm-7:15 pm

1 stop25h 45m

Gulfport Biloxi Regional

Sun 11/30

7:55 pm-4:52 pm

1 stop20h 57m

$493

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 11/24

5:47 pm-5:15 pm

1 stop23h 28m

$125

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 11 results
1
2

Compare providers for flights from Midway to Gulfport

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 Midway to Gulfport in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Chicago Midway Airport-Gulfport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Gulfport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Gulfport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Gulfport flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago Midway Airport-Gulfport 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 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Gulfport (average of $110). Flying from Chicago Midway Airport to Gulfport in March is currently the most expensive (average of $279). 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 October 28, 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
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 6h 26m. 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 $269, 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Gulfport (average of $110). Flying from Chicago Midway Airport to Gulfport in March is currently the most expensive (average of $279). 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

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$269Average$403FlexibilityNo cancel feeOn-timeN/A

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