$153+ Cheap flights from Chicago (CHI) to Gulfport (GPT)
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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Oct 22 — Oct 291
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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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 Chicago to Gulfport
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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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/17. 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 11/74:19 pm -
1 stop4h 27m
Wed 11/116:20 am -
1 stop4h 04m
Deal found 9/17![Delta logo]()
$305
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/174:45 pm -
1 stop7h 14m
Tue 10/205:39 pm -
1 stop5h 21m
Deal found 9/17![American Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 9/20. 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 11/246:49 am -
1 stop6h 15m
Tue 12/16:09 pm -
1 stop5h 43m
Deal found 9/20![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 10/196:40 pm -
1 stop5h 19m
Sat 10/2412:49 pm -
1 stop5h 02m
Deal found 9/17![American Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 9/20. 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.
Sat 11/216:00 am -
2 stops10h 18m
Wed 12/26:09 pm -
1 stop5h 43m
Deal found 9/20![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 9/20. 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.
Sun 11/226:49 am -
1 stop6h 15m
Wed 12/21:56 pm -
1 stop5h 09m
Deal found 9/20![Delta logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 12/149:19 am -
1 stop6h 49m
Thu 12/174:55 pm -
1 stop7h 49m
Deal found 9/17![United Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 9/20. 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.
Mon 11/236:23 am -
2 stops10h 56m
Tue 12/16:09 pm -
1 stop5h 43m
Deal found 9/20![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 9/16. 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 11/135:13 pm -
1 stop4h 39m
Sun 11/156:04 pm -
1 stop4h 50m
Deal found 9/16![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:45 pm -
1 stop7h 14m
Fri 11/612:43 pm -
1 stop4h 57m
Deal found 9/18![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 11/74:19 pm -
1 stop4h 27m
Tue 11/106:04 pm -
1 stop4h 50m
Deal found 9/18![Delta logo]()
$342
This Delta deal was found by Cheapflights users on 9/21. 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 11/1310:06 am -
2 stops11h 46m
Sun 11/156:04 pm -
1 stop5h 50m
Deal found 9/21![Delta logo]()
$344
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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/17. 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 11/74:19 pm -
1 stop4h 27m
Wed 11/116:20 am -
1 stop4h 04m
Deal found 9/17![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Thu 10/156:25 am -
1 stop7h 00m
Sat 10/172:00 pm -
1 stop7h 42m
Deal found 9/19![United Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 9/20. 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.
Sat 11/216:00 am -
2 stops10h 18m
Thu 11/2612:30 pm -
1 stop6h 35m
Deal found 9/20![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 9/16. 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 11/135:13 pm -
1 stop4h 39m
Sun 11/156:04 pm -
1 stop4h 50m
Deal found 9/16![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 11/74:19 pm -
1 stop4h 27m
Tue 11/106:04 pm -
1 stop4h 50m
Deal found 9/18![Delta logo]()
$342
This Delta deal was found by Cheapflights users on 9/17. 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 11/58:36 am -
2 stops12h 10m
Fri 11/136:04 pm -
1 stop5h 50m
Deal found 9/17![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 9/2611:17 am -
2 stops9h 32m
Mon 9/285:59 pm -
1 stop6h 00m
Deal found 9/18![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 9/18. 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.
Fri 9/256:00 am -
2 stops11h 14m
Tue 9/295:59 pm -
1 stop6h 00m
Deal found 9/18![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 9/17. 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 10/1711:09 am -
2 stops9h 37m
Tue 10/206:26 am -
2 stops11h 54m
Deal found 9/17![Delta logo]()
$468
This Delta deal was found by Cheapflights users on 9/19. 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.
Sat 10/34:30 pm -
1 stop4h 19m
Mon 10/55:59 pm -
1 stop4h 45m
Deal found 9/19![Delta logo]()
$509
This Delta deal was found by Cheapflights users on 9/16. 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 10/26:05 am -
1 stop6h 50m
Tue 10/66:26 am -
2 stops6h 21m
Deal found 9/16![Delta logo]()
$777
This Delta deal was found by Cheapflights users on 9/21. 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.
Thu 11/54:19 pm -
1 stop4h 27m
Fri 11/136:04 pm -
1 stop4h 50m
Deal found 9/21![Delta logo]()
$819
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated September 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:00 am -
1 stop5h 40m
Fri 10/211:18 am -
1 stop8h 18m
Deal found 9/18![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/35:20 am -
1 stop7h 52m
Wed 10/76:42 pm -
1 stop5h 26m
Deal found 9/21![American Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/144:45 pm -
1 stop7h 14m
Wed 10/216:02 pm -
1 stop5h 57m
Deal found 9/19![American Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 9/19. 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 10/146:00 am -
2 stops11h 20m
Wed 10/216:05 pm -
1 stop5h 52m
Deal found 9/19![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 9/19. 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 10/149:29 am -
2 stops7h 51m
Wed 10/216:05 pm -
1 stop4h 28m
Deal found 9/19![Delta logo]()
$414
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/156:25 am -
1 stop7h 00m
Sat 10/172:00 pm -
1 stop7h 42m
Deal found 9/20![United Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/174:45 pm -
1 stop7h 14m
Tue 10/205:39 pm -
1 stop5h 21m
Deal found 9/17![American Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 9/17. 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 10/179:29 am -
2 stops11h 17m
Tue 10/206:05 pm -
1 stop4h 28m
Deal found 9/17![Delta logo]()
$406
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 10/196:40 pm -
1 stop5h 19m
Sat 10/2412:49 pm -
1 stop5h 02m
Deal found 9/17![American Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/226:30 am -
2 stops26h 21m
Sun 10/257:45 pm -
1 stop11h 46m
Deal found 9/17![Multiple Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:45 pm -
1 stop7h 14m
Fri 11/612:43 pm -
1 stop4h 57m
Deal found 9/18![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/306:40 pm -
1 stop5h 19m
Sun 11/16:21 pm -
1 stop5h 38m
Deal found 9/17![American Airlines logo]()
$354
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 September 22, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/78:45 am -
1 stop7h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![United Airlines logo]()
$153
This Delta deal was found by Cheapflights users on 9/17. 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 10/711:19 am -
2 stops10h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Sun 10/47:11 am -
2 stops25h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/76:20 am -
3 stops36h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/76:25 am -
3 stops36h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/21. 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 9/291:00 pm -
1 stop4h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 9/21. 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 10/311:17 am -
2 stops9h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 9/17. 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 9/285:10 pm -
1 stop4h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Sun 10/45:30 am -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 9/18. 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.
Sun 10/46:05 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 9/17. 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 10/79:29 am -
2 stops7h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:28 pm -
3 stops47h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$379
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (Delta) |
One-way from | $153 (United Airlines) |
Popular in | September |
Cheapest in | February |
Average price | $796 |
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 September 22, 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
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Wed 10/7
8:45 am-4:12 pm
1 stop7h 27m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$153
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Wed 10/7
11:19 am-10:16 pm
2 stops10h 57m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$158
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Wed 10/7
6:25 am-7:05 pm
3 stops36h 40m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Wed 10/7
6:00 am-11:13 am
1 stop5h 13m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$287
Quickest round-trip
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Tue 9/29
1:00 pm-5:14 pm
1 stop4h 14m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$287
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sat 10/3
5:30 am-1:25 pm
1 stop7h 55m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$287
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 9/29
10:25 am-10:08 pm
2 stops11h 43m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$292
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Sat 11/7
4:19 pm-8:46 pm
1 stop4h 27m
Gulfport Biloxi Regional
Wed 11/11
6:20 am-10:24 am
1 stop4h 04m
$305
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Mon 9/28
5:10 pm-10:08 pm
1 stop4h 58m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$326
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sat 11/21
6:00 am-4:18 pm
2 stops10h 18m
Gulfport Biloxi Regional
Thu 11/26
12:30 pm-7:05 pm
1 stop6h 35m
$335
Showing 1-10 of 22 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 September.
| 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
MDW-GPT
ORD-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
CHI-GPT
MDW-GPT
ORD-GPT
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 $550). 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 $385 and $638 in November.The cheapest round-trip price found within the last 5 days was $305 on Delta (Nov 7-Nov 10).
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 143 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 Sunday 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 63% 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 September 22, 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.
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 September 22, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on September 22, 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 September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$472 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$519 | FlexibilityNo cancel fee | On-time71% |