$221+ Cheap flights from Gulfport (GPT) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — MDW
Oct 27 — Nov 31
Round-trip
1 adult, Economy
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Find cheap flights from Gulfport to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Gulfport to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Gulfport to MidwayExplore 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 September 27, 2026.
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 September 27, 2026.
This Delta deal was found by Cheapflights users on 9/23. 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.
Sat 11/215:05 pm -
1 stop5h 49m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 9/23. 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.
Mon 11/236:04 pm -
1 stop4h 50m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$330
This Delta deal was found by Cheapflights users on 9/23. 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 11/126:26 am -
1 stop5h 33m
Mon 11/166:00 am -
1 stop7h 04m
Deal found 9/23![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/23. 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.
Sun 11/226:04 pm -
1 stop4h 50m
Tue 12/111:28 am -
1 stop5h 56m
Deal found 9/23![Delta logo]()
$350
This Delta deal was found by Cheapflights users on 9/24. 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.
Thu 12/36:09 pm -
1 stop4h 45m
Sun 12/66:00 am -
1 stop7h 07m
Deal found 9/24![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 9/23. 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.
Tue 11/246:04 pm -
1 stop4h 50m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 9/23. 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 11/256:26 am -
2 stops10h 13m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$465
Best flights from Gulfport to MidwayDiscover carefully curated flight deals from Gulfport to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 27, 2026.
Discover carefully curated flight deals from Gulfport to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 27, 2026.
This Delta deal was found by Cheapflights users on 9/23. 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.
Mon 11/236:04 pm -
1 stop4h 50m
Tue 12/16:00 am -
1 stop7h 11m
Deal found 9/23![Delta logo]()
$330
This Delta deal was found by Cheapflights users on 9/26. 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 11/136:04 pm -
1 stop4h 50m
Mon 11/166:00 am -
1 stop7h 04m
Deal found 9/26![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/25. 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 11/126:04 pm -
1 stop4h 50m
Mon 11/1612:30 pm -
2 stops9h 22m
Deal found 9/25![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/24. 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.
Thu 12/36:09 pm -
1 stop4h 45m
Sun 12/66:00 am -
1 stop7h 07m
Deal found 9/24![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 9/23. 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.
Sat 11/215:05 pm -
1 stop5h 49m
Mon 11/305:13 pm -
1 stop4h 39m
Deal found 9/23![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 9/22. 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.
Thu 3/256:00 pm -
1 stop4h 10m
Tue 3/305:25 pm -
1 stop4h 42m
Deal found 9/22![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 9/23. 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 11/256:04 pm -
1 stop4h 50m
Mon 11/305:13 pm -
1 stop4h 39m
Deal found 9/23![Delta logo]()
$554
Last-minute flights from Gulfport to MidwayDiscover last-minute flight deals from Gulfport to Midway. Data last updated September 27, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Midway. Data last updated September 27, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/23. 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 10/15:59 pm -
1 stop4h 45m
Tue 10/610:59 am -
1 stop6h 21m
Deal found 9/23![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 9/22. 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.
Wed 10/76:05 pm -
1 stop4h 28m
Sun 10/116:04 am -
1 stop6h 57m
Deal found 9/22![Delta logo]()
$610
This Delta deal was found by Cheapflights users on 9/25. 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 10/104:00 pm -
1 stop6h 33m
Wed 10/146:04 am -
1 stop6h 57m
Deal found 9/25![Delta logo]()
$584
This Delta deal was found by Cheapflights users on 9/24. 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.
Sat 10/104:00 pm -
1 stop6h 33m
Sun 10/1110:59 am -
1 stop6h 21m
Deal found 9/24![Delta logo]()
$694
This Delta deal was found by Cheapflights users on 9/23. 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 10/216:05 pm -
1 stop4h 28m
Mon 11/21:27 pm -
2 stops7h 19m
Deal found 9/23![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 9/24. 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.
Thu 10/226:26 am -
2 stops6h 21m
Mon 10/266:04 am -
1 stop6h 57m
Deal found 9/24![Delta logo]()
$594
One-way flights from Gulfport to MidwaySearch for one-way flight options from Gulfport to Midway. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
Search for one-way flight options from Gulfport to Midway. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
This Delta deal was found by Cheapflights users on 9/23. 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.
Tue 10/206:05 pm -
1 stop4h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$221
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 September 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Delta) |
One-way from | $221 (Delta) |
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 7,457,451 searches. Data last updated September 27, 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
Cheapest round-trip
Quickest round-trip
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Tue 10/20
6:05 pm-10:33 pm
1 stop4h 28m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$221
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Mon 11/23
6:04 pm-10:54 pm
1 stop4h 50m
Chicago Midway
Tue 12/1
6:00 am-1:11 pm
1 stop7h 11m
$330
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Fri 11/13
6:04 pm-10:54 pm
1 stop4h 50m
Chicago Midway
Mon 11/16
6:00 am-1:04 pm
1 stop7h 04m
$339
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Thu 11/12
6:04 pm-10:54 pm
1 stop4h 50m
Chicago Midway
Mon 11/16
12:30 pm-9:52 pm
2 stops9h 22m
$344
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Thu 12/3
6:09 pm-10:54 pm
1 stop4h 45m
Chicago Midway
Sun 12/6
6:00 am-1:07 pm
1 stop7h 07m
$389
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Sat 11/21
5:05 pm-10:54 pm
1 stop5h 49m
Chicago Midway
Mon 11/30
5:13 pm-9:52 pm
1 stop4h 39m
$470
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Thu 3/25
6:00 pm-10:10 pm
1 stop4h 10m
Chicago Midway
Tue 3/30
5:25 pm-10:07 pm
1 stop4h 42m
$470
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Wed 11/25
6:04 pm-10:54 pm
1 stop4h 50m
Chicago Midway
Mon 11/30
5:13 pm-9:52 pm
1 stop4h 39m
$554
Sorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
GPT-MDW
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.
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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