$186+ Cheap flights from Chicago (CHI) 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Gulfport 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
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Cheapest flights from Chicago to GulfportExplore the most affordable flight options available from Chicago to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
Explore the most affordable flight options available from Chicago to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 24, 2026.
This Delta deal was found by Cheapflights users on 8/22. 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 10/65:09 pm -
1 stop5h 07m
Tue 10/1310:03 am -
1 stop6h 11m
Deal found 8/22![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/22. 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 10/68:05 am -
1 stop4h 56m
Tue 10/131:46 pm -
1 stop6h 52m
Deal found 8/22![Delta logo]()
$301
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:45 pm -
1 stop5h 47m
Tue 9/295:42 pm -
1 stop6h 17m
Deal found 8/21![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 8/23. 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 10/71:27 pm -
2 stops8h 49m
Wed 10/146:26 am -
2 stops6h 21m
Deal found 8/23![Delta logo]()
$311
This Delta deal was found by Cheapflights users on 8/19. 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 9/161:00 pm -
1 stop4h 14m
Sun 9/205:59 pm -
1 stop4h 45m
Deal found 8/19![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:59 am -
1 stop8h 13m
Sun 9/205:02 pm -
1 stop6h 28m
Deal found 8/19![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:53 am -
1 stop5h 27m
Wed 9/911:18 am -
1 stop8h 18m
Deal found 8/21![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:57 pm -
1 stop6h 19m
Sat 9/126:22 pm -
1 stop5h 52m
Deal found 8/20![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 8/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
1 stop5h 13m
Wed 10/146:02 pm -
1 stop5h 57m
Deal found 8/23![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 8/19. 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 9/24:39 pm -
1 stop5h 42m
Sat 9/54:00 pm -
1 stop6h 36m
Deal found 8/19![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/19. 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 9/23:25 pm -
1 stop6h 56m
Sat 9/54:00 pm -
1 stop4h 55m
Deal found 8/19![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/21. 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 9/13:25 pm -
1 stop6h 56m
Wed 9/305:59 pm -
1 stop6h 00m
Deal found 8/21![Delta logo]()
$351
Best flights from Chicago to GulfportDiscover carefully curated flight deals from Chicago to Gulfport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
Discover carefully curated flight deals from Chicago to Gulfport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 24, 2026.
This Delta deal was found by Cheapflights users on 8/22. 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 10/65:09 pm -
1 stop5h 07m
Tue 10/1310:03 am -
1 stop6h 11m
Deal found 8/22![Delta logo]()
$301
This American Airlines deal was found by Cheapflights users on 8/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:00 am -
1 stop5h 41m
Tue 9/155:35 am -
1 stop5h 34m
Deal found 8/23![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:55 am -
1 stop6h 23m
Fri 11/134:55 pm -
1 stop6h 31m
Deal found 8/20![United Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 10/83:30 pm -
1 stop26h 36m
Sun 10/117:45 pm -
1 stop11h 46m
Deal found 8/20![Multiple Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 8/22. 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 10/68:05 am -
1 stop4h 56m
Tue 10/131:46 pm -
1 stop6h 52m
Deal found 8/22![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/19. 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 9/161:00 pm -
1 stop4h 14m
Sun 9/205:59 pm -
1 stop4h 45m
Deal found 8/19![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/21. 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 9/13:25 pm -
1 stop6h 56m
Wed 9/305:59 pm -
1 stop6h 00m
Deal found 8/21![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 8/21. 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 9/54:39 pm -
1 stop4h 14m
Wed 9/94:00 pm -
1 stop6h 44m
Deal found 8/21![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:29 pm -
1 stop21h 43m
Tue 9/295:14 pm -
1 stop6h 13m
Deal found 8/18![United Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 8/18. 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 10/146:30 am -
1 stop6h 31m
Fri 10/1610:03 am -
1 stop6h 55m
Deal found 8/18![Delta logo]()
$386
This Delta deal was found by Cheapflights users on 8/21. 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 9/56:59 am -
2 stops8h 01m
Wed 9/96:25 am -
2 stops11h 39m
Deal found 8/21![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 8/20. 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 9/86:05 am -
1 stop7h 06m
Sat 9/124:00 pm -
1 stop6h 44m
Deal found 8/20![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 8/23. 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 10/231:27 pm -
2 stops8h 49m
Sun 10/256:05 pm -
1 stop4h 28m
Deal found 8/23![Delta logo]()
$544
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated August 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/21. 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 9/13:25 pm -
1 stop6h 56m
Wed 9/305:59 pm -
1 stop6h 00m
Deal found 8/21![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 8/19. 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 9/24:39 pm -
1 stop5h 42m
Sat 9/54:00 pm -
1 stop6h 36m
Deal found 8/19![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/19. 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 9/23:25 pm -
1 stop6h 56m
Sat 9/54:00 pm -
1 stop4h 55m
Deal found 8/19![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/19. 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 9/24:39 pm -
1 stop5h 42m
Sun 9/66:30 am -
2 stops10h 29m
Deal found 8/19![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 8/19. 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 9/210:30 am -
2 stops11h 51m
Sun 9/66:30 am -
1 stop6h 10m
Deal found 8/19![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:00 am -
1 stop5h 41m
Tue 9/155:35 am -
1 stop5h 34m
Deal found 8/23![American Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:53 am -
1 stop5h 27m
Wed 9/911:18 am -
1 stop8h 18m
Deal found 8/21![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:57 pm -
1 stop6h 19m
Sat 9/126:22 pm -
1 stop5h 52m
Deal found 8/20![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 8/19. 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 9/161:00 pm -
1 stop4h 14m
Sun 9/205:59 pm -
1 stop4h 45m
Deal found 8/19![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:59 am -
1 stop8h 13m
Sun 9/205:02 pm -
1 stop6h 28m
Deal found 8/19![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:45 pm -
1 stop5h 47m
Tue 9/295:42 pm -
1 stop6h 17m
Deal found 8/21![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 8/21. 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 9/255:10 pm -
1 stop4h 58m
Tue 9/295:59 pm -
1 stop4h 45m
Deal found 8/21![Delta logo]()
$365
One-way flights from Chicago to GulfportSearch for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:00 am -
1 stop6h 52m
Deal found 8/20![American Airlines logo]()
$186
This Delta deal was found by Cheapflights users on 8/20. 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 9/2311:30 am -
2 stops10h 38m
Deal found 8/20![Delta logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Sun 11/86:16 am -
2 stops26h 35m
Deal found 8/19![Multiple Airlines logo]()
$198
This Delta deal was found by Cheapflights users on 8/21. 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 10/56:05 am -
1 stop7h 06m
Deal found 8/21![Delta logo]()
$201
This Delta deal was found by Cheapflights users on 8/21. 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 10/56:40 am -
1 stop6h 31m
Deal found 8/21![Delta logo]()
$201
This American Airlines deal was found by Cheapflights users on 8/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:45 pm -
1 stop5h 47m
Deal found 8/23![American Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Sun 11/810:26 am -
2 stops22h 25m
Deal found 8/19![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/88:04 am -
2 stops24h 47m
Deal found 8/19![Multiple Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop7h 00m
Deal found 8/19![United Airlines logo]()
$224
This deal was found by Cheapflights users on 8/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:55 am -
1 stop6h 23m
Deal found 8/20![United Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/237:28 pm -
3 stops37h 23m
Deal found 8/20![Multiple Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 8/21. 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 9/110:54 am -
1 stop4h 06m
Deal found 8/21![Delta logo]()
$277
Find flight deals from Chicago to Gulfport
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Delta) |
One-way from | $186 (American Airlines) |
Popular in | April |
Cheapest in | February |
Average price | $296 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 7,457,451 searches. Data last updated August 24, 2026.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Tue 10/6
5:09 pm-10:16 pm
1 stop5h 07m
Gulfport Biloxi Regional
Tue 10/13
10:03 am-4:14 pm
1 stop6h 11m
$301
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 10/6
8:05 am-1:01 pm
1 stop4h 56m
Gulfport Biloxi Regional
Tue 10/13
1:46 pm-8:38 pm
1 stop6h 52m
$301
Quickest round-trip
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Wed 9/16
1:00 pm-5:14 pm
1 stop4h 14m
Gulfport Biloxi Regional
Sun 9/20
5:59 pm-10:44 pm
1 stop4h 45m
$319
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 9/1
3:25 pm-10:21 pm
1 stop6h 56m
Gulfport Biloxi Regional
Wed 9/30
5:59 pm-11:59 pm
1 stop6h 00m
$351
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Thu 9/3
5:00 am-10:41 am
1 stop5h 41m
Gulfport Biloxi Regional
Tue 9/15
5:35 am-11:09 am
1 stop5h 34m
$364
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Sat 9/5
4:39 pm-8:53 pm
1 stop4h 14m
Gulfport Biloxi Regional
Wed 9/9
4:00 pm-10:44 pm
1 stop6h 44m
$380
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Wed 10/14
6:30 am-1:01 pm
1 stop6h 31m
Gulfport Biloxi Regional
Fri 10/16
10:03 am-4:58 pm
1 stop6h 55m
$386
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sat 9/5
6:59 am-3:00 pm
2 stops8h 01m
Gulfport Biloxi Regional
Wed 9/9
6:25 am-6:04 pm
2 stops11h 39m
$390
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Thu 11/5
6:55 am-1:18 pm
1 stop6h 23m
Gulfport Biloxi Regional
Fri 11/13
4:55 pm-11:26 pm
1 stop6h 31m
$440
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Thu 10/8
3:30 pm-6:06 pm
1 stop26h 36m
Gulfport Biloxi Regional
Sun 10/11
7:45 pm-7:31 am
1 stop11h 46m
$483
Showing 1-10 of 30 resultsSorted by cheapest first
Compare providers for flights from Chicago 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 Chicago to Gulfport in August.
| 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-Gulfport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Gulfport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Gulfport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-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-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 Chicago to Gulfport
Have a flexible travel schedule? Discover the best time to fly to Gulfport from Chicago with our price prediction graph.
CHI-GPT
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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 to Gulfport
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What is the cheapest month to book a flight from Chicago to Gulfport?
Currently, February is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $289). Flying from Chicago to Gulfport in January is currently the most expensive (average of $526). 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.
How much does it cost to fly round-trip from Chicago to Gulfport?
Airfare is below average for this route at the moment.
Chicago to Gulfport flights typically cost between $310 and $546 in October.The cheapest round-trip price found within the last 5 days was $301 on Delta (Oct 6-Oct 13).
How often are flights from Chicago to Gulfport delayed?
About 58% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 126 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 61% 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 August 24, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from Chicago to Gulfport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 locationsD'Iberville
Ocean Springs
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Other flights to Gulfport
Explore flights to Gulfport departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 24, 2026.
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Top 2 airlines flying from Chicago to Gulfport
Discover the top 2 airlines that operate flights from Chicago 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 7,457,451 searches. Data last updated August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$519 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$472 | FlexibilityNo cancel fee | On-timeN/A |