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$251+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GPT
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap 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 July 27, 2026.

This Delta deal was found by Cheapflights users on 7/26. 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 9/96:05 am
MDW
-
GPT
1 stop7h 06m
Delta
Wed 9/165:59 pm
GPT
-
MDW
1 stop4h 45m
Delta
Deal found 7/26$301
This Delta deal was found by Cheapflights users on 7/23. 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 9/185:10 pm
MDW
-
GPT
1 stop4h 58m
Delta
Sat 9/194:00 pm
GPT
-
MDW
1 stop6h 44m
Delta
Deal found 7/23$310
This Delta deal was found by Cheapflights users on 7/24. 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 9/84:30 pm
MDW
-
GPT
1 stop4h 19m
Delta
Tue 9/155:59 pm
GPT
-
MDW
1 stop4h 45m
Delta
Deal found 7/24$330
This Delta deal was found by Cheapflights users on 7/23. 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 8/206:05 am
MDW
-
GPT
1 stop6h 58m
Delta
Thu 8/276:00 pm
GPT
-
MDW
1 stop4h 36m
Delta
Deal found 7/23$359
This Delta deal was found by Cheapflights users on 7/22. 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 8/45:10 pm
MDW
-
GPT
1 stop5h 11m
Delta
Sun 8/96:00 pm
GPT
-
MDW
1 stop4h 36m
Delta
Deal found 7/22$375
This Delta deal was found by Cheapflights users on 7/23. 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 8/51:25 pm
MDW
-
GPT
2 stops8h 56m
Delta
Sat 8/810:01 am
GPT
-
MDW
1 stop5h 37m
Delta
Deal found 7/23$380
This Delta deal was found by Cheapflights users on 7/27. 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 8/291:25 pm
MDW
-
GPT
2 stops7h 28m
Delta
Sat 9/510:01 am
GPT
-
MDW
2 stops6h 58m
Delta
Deal found 7/27$400
This Delta deal was found by Cheapflights users on 7/23. 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 7/296:00 am
MDW
-
GPT
1 stop7h 05m
Delta
Sat 8/14:00 pm
GPT
-
MDW
1 stop6h 15m
Delta
Deal found 7/23$401

Find 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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$301
(Delta)

One-way from

$251
(Kiwi.com)

Popular in

April

Cheapest in

February

Average price

$290
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. 15% potential increase in price ($78 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 July 2026
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 July 27, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Gulfport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 9/9

6:05 am-1:11 pm

1 stop7h 06m

Gulfport Biloxi Regional

Wed 9/16

5:59 pm-10:44 pm

1 stop4h 45m

$301

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 9/18

5:10 pm-10:08 pm

1 stop4h 58m

Gulfport Biloxi Regional

Sat 9/19

4:00 pm-10:44 pm

1 stop6h 44m

$310

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 8/20

6:05 am-1:03 pm

1 stop6h 58m

Gulfport Biloxi Regional

Thu 8/27

6:00 pm-10:36 pm

1 stop4h 36m

$359
Quickest round-trip

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 9/18

1:00 pm-5:14 pm

1 stop4h 14m

Gulfport Biloxi Regional

Sun 9/20

6:25 am-11:54 am

1 stop5h 29m

$419

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 9/8

4:30 pm-8:49 pm

1 stop4h 19m

Gulfport Biloxi Regional

Tue 9/15

10:06 am-6:33 pm

2 stops8h 27m

$424

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 8/29

4:39 pm-8:53 pm

1 stop4h 14m

Gulfport Biloxi Regional

Sat 9/5

4:00 pm-10:36 pm

1 stop6h 36m

$440
Cheapest one-way

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 8/4

6:05 am-1:03 pm

1 stop6h 58m

$267

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 8/6

6:05 am-1:03 pm

1 stop6h 58m

$306

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 8/7

9:24 am-5:15 pm

2 stops7h 51m

$311

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 9/3

6:05 am-4:51 pm

3 stops34h 46m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 12 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Gulfport flight deals on Cheapflights vs. FlightHub >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 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 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

How often are flights from Chicago to Gulfport delayed?

About 63% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 131 minutes.

What is the most punctual flight time for Chicago to Gulfport flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Gulfport flights?

Over the last year, Sun Country Air have had the lowest number of delays on this route, with just 64% of flights being delayed.

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 July 27, 2026.
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
7.8
Good
8,490 reviews

Comfort

7.8

Entertainment

7.8

Overall

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,490 reviews
Delta
7.8
Good
8,490 reviews

Comfort

7.8

Entertainment

7.8

Overall

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 7h 06m. 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.

  • 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.

See more FAQs

Traveling to a place near Gulfport?

Book flights to Gulfport if you plan to visit one of these locations
D'Iberville
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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$269Average$516FlexibilityNo cancel feeOn-timeN/A

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