$137+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GPT
Touko 29 — kesä 51
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Gulfport with Cheapflights
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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
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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 Midway to Gulfport
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Cheapest flights from Midway to GulfportExplore 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 huhtikuu 29, 2026.
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 huhtikuu 29, 2026.
This Delta deal was found by Cheapflights users on 4/28. 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.
ti 6/25:15 pm
MDW
- GPT
1 stop4h 36m
Delta
ti 6/95:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 4/28![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 4/27. 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.
ti 7/76:00 am
MDW
- GPT
1 stop7h 05m
Delta
pe 7/316:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 4/27![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 4/24. 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.
la 5/95:29 pm
MDW
- GPT
1 stop4h 22m
Delta
ke 5/136:32 am
GPT
- MDW
1 stop5h 24m
Delta
Deal found 4/24![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 4/27. 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.
pe 6/55:08 pm
MDW
- GPT
1 stop4h 43m
Delta
pe 6/125:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 4/27![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 4/24. 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.
ma 5/115:10 pm
MDW
- GPT
1 stop4h 41m
Delta
la 5/163:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/24![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 4/26. 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.
ti 8/46:05 am
MDW
- GPT
1 stop7h 00m
Delta
su 8/96:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 4/26![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 4/28. 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.
pe 5/812:53 pm
MDW
- GPT
1 stop4h 21m
Delta
to 5/141:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/28![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 4/27. 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.
to 5/76:23 am
MDW
- GPT
1 stop6h 46m
Delta
la 5/910:08 am
GPT
- MDW
1 stop6h 24m
Delta
Deal found 4/27![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 4/28. 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.
pe 5/226:23 am
MDW
- GPT
1 stop6h 46m
Delta
ti 5/261:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/28![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 4/27. 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.
to 5/216:23 am
MDW
- GPT
1 stop6h 46m
Delta
pe 5/291:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/27![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 4/27. 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.
to 7/166:00 am
MDW
- GPT
1 stop7h 05m
Delta
su 7/196:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 4/27![Delta logo]()
$488
Best flights from Midway to GulfportDiscover carefully curated flight deals from Midway to Gulfport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated huhtikuu 29, 2026.
Discover carefully curated flight deals from Midway to Gulfport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated huhtikuu 29, 2026.
This Delta deal was found by Cheapflights users on 4/28. 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.
ti 6/25:15 pm
MDW
- GPT
1 stop4h 36m
Delta
ti 6/95:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 4/28![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 4/27. 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.
ti 7/76:00 am
MDW
- GPT
1 stop7h 05m
Delta
pe 7/316:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 4/27![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 4/24. 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.
la 5/95:29 pm
MDW
- GPT
1 stop4h 22m
Delta
ke 5/136:32 am
GPT
- MDW
1 stop5h 24m
Delta
Deal found 4/24![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 4/25. 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.
ma 5/115:10 pm
MDW
- GPT
1 stop4h 41m
Delta
la 5/163:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/25![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 4/26. 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.
ti 8/46:05 am
MDW
- GPT
1 stop7h 00m
Delta
su 8/96:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 4/26![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 4/28. 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.
pe 5/226:23 am
MDW
- GPT
1 stop6h 46m
Delta
ti 5/261:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/28![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 4/27. 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.
to 5/216:23 am
MDW
- GPT
1 stop6h 46m
Delta
pe 5/291:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/27![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 4/26. 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.
to 7/166:00 am
MDW
- GPT
1 stop7h 05m
Delta
su 7/196:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 4/26![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 4/28. 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.
to 10/11:05 pm
MDW
- GPT
1 stop4h 12m
Delta
su 10/46:00 am
GPT
- MDW
1 stop5h 54m
Delta
Deal found 4/28![Delta logo]()
$578
This Delta deal was found by Cheapflights users on 4/27. 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.
la 6/65:30 pm
MDW
- GPT
1 stop4h 21m
Delta
la 6/133:00 pm
GPT
- MDW
1 stop7h 17m
Delta
Deal found 4/27![Delta logo]()
$579
This Delta deal was found by Cheapflights users on 4/24. 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.
su 5/1010:59 am
MDW
- GPT
1 stop6h 15m
Delta
to 5/141:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/24![Delta logo]()
$601
This Delta deal was found by Cheapflights users on 4/26. 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.
la 5/235:10 pm
MDW
- GPT
1 stop4h 41m
Delta
ma 5/256:32 am
GPT
- MDW
1 stop5h 24m
Delta
Deal found 4/26![Delta logo]()
$949
Last-minute flights from Midway to GulfportDiscover last-minute flight deals from Midway to Gulfport. Data last updated huhtikuu 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Gulfport. Data last updated huhtikuu 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/27. 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.
to 5/76:23 am
MDW
- GPT
1 stop6h 46m
Delta
la 5/910:08 am
GPT
- MDW
1 stop6h 24m
Delta
Deal found 4/27![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 4/28. 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.
pe 5/812:53 pm
MDW
- GPT
1 stop4h 21m
Delta
to 5/141:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/28![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 4/24. 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.
la 5/95:29 pm
MDW
- GPT
1 stop4h 22m
Delta
ke 5/136:32 am
GPT
- MDW
1 stop5h 24m
Delta
Deal found 4/24![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 4/24. 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.
ma 5/115:10 pm
MDW
- GPT
1 stop4h 41m
Delta
la 5/163:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/24![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 4/28. 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.
ke 5/1310:59 am
MDW
- GPT
1 stop6h 15m
Delta
su 5/171:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/28![Delta logo]()
$499
This Delta deal was found by Cheapflights users on 4/27. 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.
to 5/216:23 am
MDW
- GPT
1 stop6h 46m
Delta
pe 5/291:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/27![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 4/26. 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.
to 5/216:23 am
MDW
- GPT
1 stop6h 46m
Delta
ti 5/261:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/26![Delta logo]()
$509
This Delta deal was found by Cheapflights users on 4/28. 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.
pe 5/226:23 am
MDW
- GPT
1 stop6h 46m
Delta
ti 5/261:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/28![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 4/26. 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.
pe 5/226:23 am
MDW
- GPT
1 stop6h 46m
Delta
ma 5/256:32 am
GPT
- MDW
1 stop5h 24m
Delta
Deal found 4/26![Delta logo]()
$539
One-way flights from Midway to GulfportSearch for one-way flight options from Midway to Gulfport. Find affordable one-way fares based on user searches. Data last updated huhtikuu 29, 2026.
Search for one-way flight options from Midway to Gulfport. Find affordable one-way fares based on user searches. Data last updated huhtikuu 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
to 5/286:00 am
MDW
- GPT
2 stops25h 41m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$137
This Delta deal was found by Cheapflights users on 4/26. 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.
to 5/285:10 pm
MDW
- GPT
1 stop4h 41m
Delta
Deal found 4/26![Delta logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
su 6/216:00 am
MDW
- GPT
2 stops25h 41m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
ti 5/1212:24 pm
MDW
- GPT
3 stops54h 46m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 4/27. 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.
ti 5/125:10 pm
MDW
- GPT
1 stop4h 41m
Delta
Deal found 4/27![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 4/25. 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.
su 6/2112:45 pm
MDW
- GPT
1 stop4h 26m
Delta
Deal found 4/25![Delta logo]()
$660
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 huhtikuu 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $137 (Kiwi.com) |
Popular in | November |
Cheapest in | August |
Average price | $409 |
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 huhtikuu 29, 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
Cheapest round-trip
Quickest round-trip
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
ti 6/2
5:15 pm-9:51 pm
1 stop4h 36m
Gulfport Biloxi Regional
ti 6/9
5:56 pm-10:17 pm
1 stop4h 21m
$317
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
ti 7/7
6:00 am-1:05 pm
1 stop7h 05m
Gulfport Biloxi Regional
pe 7/31
6:00 pm-10:15 pm
1 stop4h 15m
$335
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
la 5/9
5:29 pm-9:51 pm
1 stop4h 22m
Gulfport Biloxi Regional
ke 5/13
6:32 am-11:56 am
1 stop5h 24m
$339
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
ma 5/11
5:10 pm-9:51 pm
1 stop4h 41m
Gulfport Biloxi Regional
la 5/16
3:00 pm-9:09 pm
1 stop6h 09m
$389
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
ti 8/4
6:05 am-1:05 pm
1 stop7h 00m
Gulfport Biloxi Regional
su 8/9
6:00 pm-10:15 pm
1 stop4h 15m
$414
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
pe 5/22
6:23 am-1:09 pm
1 stop6h 46m
Gulfport Biloxi Regional
ti 5/26
1:55 pm-9:09 pm
1 stop7h 14m
$478
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
to 5/21
6:23 am-1:09 pm
1 stop6h 46m
Gulfport Biloxi Regional
pe 5/29
1:55 pm-9:09 pm
1 stop7h 14m
$484
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
to 7/16
6:00 am-1:05 pm
1 stop7h 05m
Gulfport Biloxi Regional
su 7/19
6:00 pm-10:15 pm
1 stop4h 15m
$537
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
to 10/1
1:05 pm-5:17 pm
1 stop4h 12m
Gulfport Biloxi Regional
su 10/4
6:00 am-11:54 am
1 stop5h 54m
$578
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
la 6/6
5:30 pm-9:51 pm
1 stop4h 21m
Gulfport Biloxi Regional
la 6/13
3:00 pm-10:17 pm
1 stop7h 17m
$579
Showing 1-10 of 18 resultsSorted by cheapest first
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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
MDW-GPT
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 44% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 123 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 Tuesday 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 50% 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 huhtikuu 29, 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.
Overall
7.9
Crew
8.5
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Crew
8.5
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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.
Traveling to a place near Gulfport?
Book flights to Gulfport if you plan to visit one of these locationsOcean Springs
D'Iberville
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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 huhtikuu 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$269 | Average$428 | FlexibilityNo cancel fee | On-timeN/A |