$149+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Sep 14 — Sep 211
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 August 15, 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 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/2210:26 am -
2 stops22h 25m
Sun 10/257:45 pm -
1 stop11h 46m
Deal found 8/15![Multiple Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 8/12. 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 9/264:30 pm -
1 stop4h 19m
Sat 10/36:29 am -
1 stop4h 07m
Deal found 8/12![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/84:53 pm -
1 stop5h 37m
Tue 9/1511:18 am -
1 stop7h 07m
Deal found 8/11![American Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/265:00 am -
1 stop5h 40m
Sat 10/31:42 pm -
1 stop5h 56m
Deal found 8/12![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/216:29 am -
1 stop6h 43m
Thu 9/245:42 pm -
1 stop6h 17m
Deal found 8/13![American Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/15. 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 9/296:40 am -
1 stop6h 31m
Tue 10/61:46 pm -
1 stop5h 25m
Deal found 8/15![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/11. 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 9/86:40 am -
1 stop6h 31m
Tue 9/151:59 pm -
2 stops8h 19m
Deal found 8/11![Delta logo]()
$302
This American Airlines deal was found by Cheapflights users on 8/10. 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 9/103:50 pm -
1 stop7h 09m
Wed 9/165:42 pm -
1 stop6h 17m
Deal found 8/10![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/185:00 am -
1 stop5h 40m
Sat 9/195:42 pm -
1 stop6h 19m
Deal found 8/14![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:27 pm -
2 stops8h 49m
Sat 10/2410:03 am -
1 stop5h 14m
Deal found 8/15![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:55 pm -
2 stops8h 21m
Sat 10/2410:03 am -
1 stop7h 00m
Deal found 8/15![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/14. 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 9/286:05 am -
1 stop7h 06m
Mon 10/55:59 pm -
1 stop4h 45m
Deal found 8/14![Delta logo]()
$319
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 15, 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 15, 2026.
This Delta deal was found by Cheapflights users on 8/15. 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 9/291:55 pm -
2 stops8h 13m
Tue 10/61:46 pm -
1 stop6h 52m
Deal found 8/15![Delta logo]()
$306
This United Airlines deal was found by Cheapflights users on 8/11. 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 9/27:30 am -
1 stop5h 54m
Sun 9/62:00 pm -
1 stop7h 31m
Deal found 8/11![United Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:27 pm -
2 stops8h 49m
Sat 10/2410:03 am -
1 stop5h 14m
Deal found 8/15![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/14. 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 9/286:05 am -
1 stop7h 06m
Mon 10/55:59 pm -
1 stop4h 45m
Deal found 8/14![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:55 pm -
2 stops8h 21m
Sat 10/246:26 am -
2 stops10h 54m
Deal found 8/15![Delta logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/10. 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 9/65:30 am -
1 stop7h 54m
Sat 9/122:00 pm -
1 stop6h 05m
Deal found 8/10![United Airlines logo]()
$388
This Delta deal was found by Cheapflights users on 8/12. 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 11/105:09 pm -
1 stop4h 53m
Fri 11/136:04 pm -
1 stop4h 52m
Deal found 8/12![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 8/12. 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 11/109:59 am -
2 stops12h 03m
Fri 11/131:53 pm -
1 stop6h 55m
Deal found 8/12![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 8/11. 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.
Sat 9/57:30 am -
1 stop5h 54m
Fri 9/112:00 pm -
1 stop7h 32m
Deal found 8/11![United Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 10/317:30 am -
1 stop5h 48m
Wed 11/44:55 pm -
2 stops13h 41m
Deal found 8/13![United Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 8/13. 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 8/2812:46 pm -
1 stop4h 29m
Tue 9/14:00 pm -
1 stop6h 36m
Deal found 8/13![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/13. 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 8/281:00 pm -
2 stops9h 21m
Tue 9/14:00 pm -
1 stop4h 55m
Deal found 8/13![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 8/10. 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 9/106:05 am -
1 stop7h 06m
Wed 9/165:59 pm -
1 stop4h 45m
Deal found 8/10![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 8/14. 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 8/2112:46 pm -
1 stop4h 29m
Fri 8/286:00 pm -
1 stop4h 36m
Deal found 8/14![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:55 pm -
2 stops8h 21m
Fri 10/231:46 pm -
1 stop5h 25m
Deal found 8/12![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 8/10. 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 9/106:40 am -
1 stop6h 31m
Wed 9/161:59 pm -
2 stops8h 19m
Deal found 8/10![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 8/14. 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 10/131:55 pm -
2 stops8h 21m
Sat 10/176:26 am -
2 stops10h 54m
Deal found 8/14![Delta logo]()
$438
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated August 15, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/13. 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 8/2812:46 pm -
1 stop4h 29m
Tue 9/14:00 pm -
1 stop6h 36m
Deal found 8/13![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/84:53 pm -
1 stop5h 37m
Tue 9/1511:18 am -
1 stop7h 07m
Deal found 8/11![American Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 8/11. 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 9/86:40 am -
1 stop6h 31m
Tue 9/151:59 pm -
2 stops8h 19m
Deal found 8/11![Delta logo]()
$302
This American Airlines deal was found by Cheapflights users on 8/10. 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 9/103:50 pm -
1 stop7h 09m
Wed 9/165:42 pm -
1 stop6h 17m
Deal found 8/10![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/185:00 am -
1 stop5h 40m
Sat 9/195:42 pm -
1 stop6h 19m
Deal found 8/14![American Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/216:29 am -
1 stop6h 43m
Thu 9/245:42 pm -
1 stop6h 17m
Deal found 8/13![American Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/12. 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 9/264:30 pm -
1 stop4h 19m
Sat 10/36:29 am -
1 stop4h 07m
Deal found 8/12![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/265:00 am -
1 stop5h 40m
Sat 10/31:42 pm -
1 stop5h 56m
Deal found 8/12![American Airlines logo]()
$298
This Delta deal was found by Cheapflights users on 8/14. 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 9/286:05 am -
1 stop7h 06m
Mon 10/55:59 pm -
1 stop4h 45m
Deal found 8/14![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/285:20 am -
1 stop7h 52m
Mon 10/56:02 pm -
1 stop5h 57m
Deal found 8/14![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/15. 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 9/296:05 am -
1 stop7h 06m
Tue 10/66:05 pm -
1 stop4h 28m
Deal found 8/15![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/15. 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 9/296:40 am -
1 stop6h 31m
Tue 10/61:46 pm -
1 stop5h 25m
Deal found 8/15![Delta logo]()
$301
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 15, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
This Delta deal was found by Cheapflights users on 8/12. 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 9/96:05 am -
1 stop7h 06m
Deal found 8/12![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 8/11. 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 9/198:05 am -
1 stop6h 13m
Deal found 8/11![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 8/13. 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 9/610:56 am -
1 stop4h 04m
Deal found 8/13![Delta logo]()
$164
This United Airlines deal was found by Cheapflights users on 8/13. 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 9/67:30 am -
1 stop5h 54m
Deal found 8/13![United Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 8/11. 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 9/256:40 am -
1 stop6h 31m
Deal found 8/11![Delta logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/67:05 am -
2 stops24h 36m
Deal found 8/13![Multiple Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/611:50 am -
2 stops19h 51m
Deal found 8/13![Multiple Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 8/14. 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 9/286:05 am -
1 stop7h 06m
Deal found 8/14![Delta logo]()
$201
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/285:00 am -
1 stop5h 40m
Deal found 8/14![American Airlines logo]()
$201
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/215:00 am -
1 stop5h 40m
Deal found 8/11![American Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 8/12. 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 9/911:17 am -
2 stops9h 32m
Deal found 8/12![Delta logo]()
$235
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Sun 9/205:00 am -
1 stop5h 40m
Deal found 8/11![American Airlines logo]()
$241
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 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $260 (Kiwi.com) |
One-way from | $149 (Delta) |
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 2,558,603 searches. Data last updated August 15, 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
Tue 9/29
1:55 pm-10:08 pm
2 stops8h 13m
Gulfport Biloxi Regional
Tue 10/6
1:46 pm-8:38 pm
1 stop6h 52m
$306
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Thu 10/22
1:27 pm-10:16 pm
2 stops8h 49m
Gulfport Biloxi Regional
Sat 10/24
10:03 am-3:17 pm
1 stop5h 14m
$315
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Mon 9/28
6:05 am-1:11 pm
1 stop7h 06m
Gulfport Biloxi Regional
Mon 10/5
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
Thu 10/22
1:55 pm-10:16 pm
2 stops8h 21m
Gulfport Biloxi Regional
Sat 10/24
6:26 am-5:20 pm
2 stops10h 54m
$320
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Tue 11/10
5:09 pm-10:02 pm
1 stop4h 53m
Gulfport Biloxi Regional
Fri 11/13
6:04 pm-10:56 pm
1 stop4h 52m
$323
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 11/10
9:59 am-10:02 pm
2 stops12h 03m
Gulfport Biloxi Regional
Fri 11/13
1:53 pm-8:48 pm
1 stop6h 55m
$328
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Fri 8/28
12:46 pm-5:15 pm
1 stop4h 29m
Gulfport Biloxi Regional
Tue 9/1
4:00 pm-10:36 pm
1 stop6h 36m
$349
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Fri 8/28
1:00 pm-10:21 pm
2 stops9h 21m
Gulfport Biloxi Regional
Tue 9/1
4:00 pm-8:55 pm
1 stop4h 55m
$354
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Thu 9/10
6:05 am-1:11 pm
1 stop7h 06m
Gulfport Biloxi Regional
Wed 9/16
5:59 pm-10:44 pm
1 stop4h 45m
$377
Quickest round-trip
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Fri 8/21
12:46 pm-5:15 pm
1 stop4h 29m
Gulfport Biloxi Regional
Fri 8/28
6:00 pm-10:36 pm
1 stop4h 36m
$379
Showing 1-10 of 33 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
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 $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 often are flights from Chicago to Gulfport delayed?
About 61% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 125 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 64% 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 15, 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.
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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 15, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on August 15, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated August 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$519 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$601 | FlexibilityNo cancel fee | On-timeN/A |