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$133+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GPT
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:30 am
MDW
-
GPT
1 stop11h 10m
Multiple Airlines
Sun 3/87:20 pm
GPT
-
MDW
1 stop17h 48m
Multiple Airlines
Deal found 1/26$254
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:00 am
MDW
-
GPT
1 stop7h 40m
Multiple Airlines
Sun 3/157:20 pm
GPT
-
MDW
1 stop17h 48m
Multiple Airlines
Deal found 1/26$280
This Delta deal was found by Cheapflights users on 1/26. 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 7/281:05 pm
MDW
-
GPT
1 stop4h 12m
Delta
Sat 8/13:00 pm
GPT
-
MDW
1 stop6h 46m
Delta
Deal found 1/26$314
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1911:00 am
MDW
-
GPT
1 stop7h 40m
Multiple Airlines
Sun 3/227:20 pm
GPT
-
MDW
1 stop17h 48m
Multiple Airlines
Deal found 1/25$346
This Delta deal was found by Cheapflights users on 1/27. 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 2/510:48 am
MDW
-
GPT
1 stop6h 27m
Delta
Mon 2/96:08 pm
GPT
-
MDW
1 stop4h 14m
Delta
Deal found 1/27$359
This Delta deal was found by Cheapflights users on 1/25. 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.
Thu 3/512:45 pm
MDW
-
GPT
1 stop4h 30m
Delta
Tue 3/105:57 pm
GPT
-
MDW
1 stop4h 34m
Delta
Deal found 1/25$374
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:30 am
MDW
-
GPT
1 stop11h 10m
Multiple Airlines
Mon 3/99:40 am
GPT
-
MDW
2 stops13h 40m
Multiple Airlines
Deal found 1/25$398
This Delta deal was found by Cheapflights users on 1/26. 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 3/1112:47 pm
MDW
-
GPT
1 stop4h 24m
Delta
Sat 3/149:48 am
GPT
-
MDW
1 stop5h 37m
Delta
Deal found 1/26$404
This Delta deal was found by Cheapflights users on 1/25. 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.
Sat 2/74:30 pm
MDW
-
GPT
1 stop5h 23m
Delta
Sun 2/156:00 am
GPT
-
MDW
1 stop4h 06m
Delta
Deal found 1/25$409

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$254
(Kiwi.com)

One-way from

$133
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$430
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. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 27, 2026.
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

Thu 3/12

11:00 am-6:40 pm

1 stop7h 40m

Gulfport Biloxi Regional

Sun 3/15

7:20 pm-1:08 pm

1 stop17h 48m

$280

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/19

11:00 am-6:40 pm

1 stop7h 40m

Gulfport Biloxi Regional

Sun 3/22

7:20 pm-1:08 pm

1 stop17h 48m

$346

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/5

12:45 pm-5:15 pm

1 stop4h 30m

Gulfport Biloxi Regional

Mon 3/9

5:57 pm-10:31 pm

1 stop4h 34m

$374

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/5

12:45 pm-5:15 pm

1 stop4h 30m

Gulfport Biloxi Regional

Tue 3/10

5:57 pm-10:31 pm

1 stop4h 34m

$374

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/5

12:45 pm-5:15 pm

1 stop4h 30m

Gulfport Biloxi Regional

Wed 3/11

6:00 am-12:02 pm

1 stop6h 02m

$374

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 3/5

7:30 am-6:40 pm

1 stop11h 10m

Gulfport Biloxi Regional

Mon 3/9

9:40 am-11:20 pm

2 stops13h 40m

$398

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 3/11

12:47 pm-5:11 pm

1 stop4h 24m

Gulfport Biloxi Regional

Sat 3/14

9:48 am-3:25 pm

1 stop5h 37m

$404

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 2/7

4:30 pm-9:53 pm

1 stop5h 23m

Gulfport Biloxi Regional

Sun 2/15

6:00 am-10:06 am

1 stop4h 06m

$409

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 3/4

12:45 pm-9:54 pm

1 stop9h 09m

Gulfport Biloxi Regional

Wed 3/11

5:57 pm-10:31 pm

1 stop4h 34m

$419

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Mon 3/16

6:34 pm-8:50 am

2 stops14h 16m

Gulfport Biloxi Regional

Fri 3/20

5:57 pm-8:53 am

2 stops14h 56m

$462

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 15 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 January.
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

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 $267). 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 January 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
7.9
Good
8,118 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,118 reviews
Delta
7.9
Good
8,118 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 4h 30m. 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, 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 $267). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$253Average$323FlexibilityNo cancel feeOn-timeN/A

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