$123+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Mar 16 — Mar 231
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 February 14, 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 February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:25 am
ORD
- GPT
1 stop8h 45m
Multiple Airlines
Fri 5/155:31 pm
GPT
- ORD
1 stop6h 27m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:25 am
ORD
- GPT
1 stop8h 45m
Multiple Airlines
Sun 5/107:50 pm
GPT
- ORD
2 stops27h 26m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:25 am
ORD
- GPT
1 stop8h 15m
Multiple Airlines
Fri 5/85:31 pm
GPT
- ORD
1 stop18h 12m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:05 am
ORD
- GPT
1 stop10h 35m
Multiple Airlines
Sun 3/157:20 pm
GPT
- ORD
1 stop28h 18m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1211:25 am
ORD
- GPT
1 stop21h 35m
Multiple Airlines
Thu 4/167:20 pm
GPT
- ORD
1 stop18h 57m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:14 am
MDW
- GPT
1 stop9h 56m
Multiple Airlines
Fri 5/155:31 pm
GPT
- MDW
2 stops26h 00m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:25 am
ORD
- GPT
1 stop8h 15m
Multiple Airlines
Mon 4/279:40 am
GPT
- ORD
1 stop21h 07m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$266
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Sat 3/75:00 am
ORD
- GPT
1 stop5h 13m
American Airlines
Wed 3/114:29 pm
GPT
- ORD
1 stop7h 37m
American Airlines
Deal found 2/10![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/104:04 pm
ORD
- GPT
2 stops7h 45m
American Airlines
Sat 3/144:29 pm
GPT
- ORD
1 stop7h 29m
American Airlines
Deal found 2/10![American Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 3/119:50 am
ORD
- GPT
1 stop7h 21m
Delta
Wed 3/185:57 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 2/11![Delta logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:30 am
MDW
- GPT
1 stop11h 10m
Multiple Airlines
Thu 3/57:20 pm
GPT
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- GPT
2 stops13h 10m
Multiple Airlines
Sun 5/107:50 pm
GPT
- MDW
1 stop12h 14m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$327
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 February 14, 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 February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1212:00 pm
ORD
- GPT
2 stops21h 00m
Multiple Airlines
Thu 4/167:20 pm
GPT
- ORD
1 stop18h 57m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 2/11. 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 5/2712:40 pm
ORD
- GPT
1 stop7h 02m
United Airlines
Mon 6/15:15 pm
GPT
- ORD
1 stop7h 30m
United Airlines
Deal found 2/11![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 2/11. 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 4/73:26 pm
ORD
- GPT
1 stop8h 00m
American Airlines
Tue 4/145:49 pm
GPT
- ORD
1 stop6h 05m
American Airlines
Deal found 2/11![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 2/12. 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 3/1210:45 am
MDW
- GPT
1 stop6h 26m
Delta
Thu 3/195:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/12![Delta logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:25 am
ORD
- GPT
1 stop8h 15m
Multiple Airlines
Mon 4/279:40 am
GPT
- ORD
1 stop21h 07m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$266
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/104:04 pm
ORD
- GPT
2 stops7h 45m
American Airlines
Sat 3/144:29 pm
GPT
- ORD
1 stop7h 29m
American Airlines
Deal found 2/10![American Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:05 am
ORD
- GPT
1 stop10h 35m
Multiple Airlines
Fri 3/136:54 pm
GPT
- ORD
1 stop23h 32m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 4/202:05 pm
ORD
- GPT
1 stop5h 48m
United Airlines
Mon 4/275:15 pm
GPT
- ORD
1 stop7h 30m
United Airlines
Deal found 2/10![United Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/174:00 pm
ORD
- GPT
1 stop7h 49m
American Airlines
Sat 3/214:29 pm
GPT
- ORD
1 stop7h 29m
American Airlines
Deal found 2/10![American Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 2/12. 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 3/1210:45 am
MDW
- GPT
1 stop6h 26m
Delta
Mon 3/165:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/12![Delta logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/254:51 pm
ORD
- GPT
2 stops25h 49m
Multiple Airlines
Mon 3/306:54 pm
GPT
- ORD
1 stop19h 58m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 2/12. 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.
Fri 5/86:30 am
MDW
- GPT
1 stop6h 38m
Delta
Mon 5/111:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 2/12![Delta logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:30 am
MDW
- GPT
1 stop11h 10m
Multiple Airlines
Thu 3/57:20 pm
GPT
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 2/10. 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 4/235:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Mon 4/275:55 pm
GPT
- MDW
1 stop4h 33m
Delta
Deal found 2/10![Delta logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/129:30 am
ORD
- GPT
1 stop9h 10m
Multiple Airlines
Mon 3/166:54 pm
GPT
- ORD
1 stop19h 04m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/1012:47 pm
MDW
- GPT
1 stop4h 24m
Delta
Sat 3/149:48 am
GPT
- MDW
1 stop5h 37m
Delta
Deal found 2/10![Delta logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:58 pm
ORD
- GPT
2 stops24h 42m
Multiple Airlines
Sun 3/17:20 pm
GPT
- ORD
1 stop24h 27m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 2/10. 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.
Fri 5/296:30 am
MDW
- GPT
1 stop6h 38m
Delta
Mon 6/11:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 2/10![Delta logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:14 am
MDW
- GPT
1 stop9h 56m
Multiple Airlines
Sun 5/107:50 pm
GPT
- MDW
1 stop12h 14m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 2/12. 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 3/2510:45 am
MDW
- GPT
1 stop6h 26m
Delta
Mon 3/305:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/12![Delta logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/129:10 am
MDW
- GPT
1 stop9h 30m
Multiple Airlines
Thu 3/197:20 pm
GPT
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:14 am
MDW
- GPT
1 stop9h 26m
Multiple Airlines
Fri 5/88:21 am
GPT
- MDW
2 stops14h 00m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:14 am
MDW
- GPT
1 stop9h 26m
Multiple Airlines
Mon 4/279:40 am
GPT
- MDW
2 stops12h 41m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$404
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated February 14, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated February 14, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/11. 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 2/216:45 am
ORD
- GPT
1 stop7h 21m
Delta
Sat 2/283:00 pm
GPT
- ORD
1 stop4h 19m
Delta
Deal found 2/11![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Sat 2/285:00 am
ORD
- GPT
1 stop5h 13m
American Airlines
Wed 3/46:31 am
GPT
- ORD
1 stop6h 04m
American Airlines
Deal found 2/13![American Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:35 am
ORD
- GPT
1 stop11h 05m
Multiple Airlines
Thu 3/57:20 pm
GPT
- ORD
1 stop22h 26m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:30 am
MDW
- GPT
1 stop11h 10m
Multiple Airlines
Thu 3/57:20 pm
GPT
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Sat 3/75:00 am
ORD
- GPT
1 stop5h 13m
American Airlines
Wed 3/114:29 pm
GPT
- ORD
1 stop7h 37m
American Airlines
Deal found 2/10![American Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:05 am
ORD
- GPT
1 stop10h 35m
Multiple Airlines
Sun 3/157:20 pm
GPT
- ORD
1 stop28h 18m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:05 am
ORD
- GPT
1 stop10h 35m
Multiple Airlines
Fri 3/136:54 pm
GPT
- ORD
1 stop23h 32m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/104:04 pm
ORD
- GPT
2 stops7h 45m
American Airlines
Sat 3/144:29 pm
GPT
- ORD
1 stop7h 29m
American Airlines
Deal found 2/10![American Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 3/119:50 am
ORD
- GPT
1 stop7h 21m
Delta
Wed 3/185:57 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 2/11![Delta logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/129:30 am
ORD
- GPT
1 stop9h 10m
Multiple Airlines
Mon 3/166:54 pm
GPT
- ORD
2 stops13h 29m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/174:00 pm
ORD
- GPT
1 stop7h 49m
American Airlines
Sat 3/214:29 pm
GPT
- ORD
1 stop7h 29m
American Airlines
Deal found 2/10![American Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/254:51 pm
ORD
- GPT
2 stops25h 49m
Multiple Airlines
Mon 3/306:54 pm
GPT
- ORD
1 stop19h 58m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$302
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 February 14, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Wed 3/114:18 pm
ORD
- GPT
1 stop26h 22m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 8/97:00 am
ORD
- GPT
1 stop24h 41m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Wed 3/1111:25 am
MDW
- GPT
2 stops31h 15m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:44 am
ORD
- GPT
1 stop7h 56m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:30 am
MDW
- GPT
1 stop11h 10m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/246:44 pm
ORD
- GPT
1 stop5h 05m
American Airlines
Deal found 2/10![American Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/2412:47 pm
MDW
- GPT
1 stop4h 24m
Delta
Deal found 2/10![Delta logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/159:30 am
ORD
- GPT
1 stop9h 10m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 2/13. 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.
Wed 3/1112:47 pm
MDW
- GPT
1 stop4h 24m
Delta
Deal found 2/13![Delta logo]()
$240
This Delta deal was found by Cheapflights users on 2/12. 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.
Sun 3/12:46 pm
ORD
- GPT
1 stop7h 08m
Delta
Deal found 2/12![Delta logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/159:10 am
MDW
- GPT
1 stop9h 30m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 2/13. 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 8/910:35 am
MDW
- GPT
1 stop6h 42m
Delta
Deal found 2/13![Delta logo]()
$308
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 February 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Kiwi.com) |
One-way from | $123 (Kiwi.com) |
Popular in | November |
Cheapest in | August |
Average price | $289 |
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 February 14, 2026.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.
Fly from
Chicago
Fly to
Gulfport
Route
Depart
Return
Price
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sun 4/12
12:00 pm-9:00 am
2 stops21h 00m
Gulfport Biloxi Regional
Thu 4/16
7:20 pm-2:17 pm
1 stop18h 57m
$257
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 4/23
10:25 am-6:40 pm
1 stop8h 15m
Gulfport Biloxi Regional
Mon 4/27
9:40 am-6:47 am
1 stop21h 07m
$266
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Wed 5/27
12:40 pm-7:42 pm
1 stop7h 02m
Gulfport Biloxi Regional
Mon 6/1
5:15 pm-12:45 am
1 stop7h 30m
$269
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 4/7
3:26 pm-11:26 pm
1 stop8h 00m
Gulfport Biloxi Regional
Tue 4/14
5:49 pm-11:54 pm
1 stop6h 05m
$269
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 3/10
4:04 pm-11:49 pm
2 stops7h 45m
Gulfport Biloxi Regional
Sat 3/14
4:29 pm-11:58 pm
1 stop7h 29m
$274
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sun 3/8
8:05 am-6:40 pm
1 stop10h 35m
Gulfport Biloxi Regional
Fri 3/13
6:54 pm-6:26 pm
1 stop23h 32m
$299
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Wed 3/25
4:51 pm-6:40 pm
2 stops25h 49m
Gulfport Biloxi Regional
Mon 3/30
6:54 pm-2:52 pm
1 stop19h 58m
$302
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 3/17
4:00 pm-11:49 pm
1 stop7h 49m
Gulfport Biloxi Regional
Sat 3/21
4:29 pm-11:58 pm
1 stop7h 29m
$304
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Sun 3/1
7:30 am-6:40 pm
1 stop11h 10m
Gulfport Biloxi Regional
Thu 3/5
7:20 pm-1:08 pm
1 stop17h 48m
$319
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 3/12
9:30 am-6:40 pm
1 stop9h 10m
Gulfport Biloxi Regional
Mon 3/16
6:54 pm-1:58 pm
1 stop19h 04m
$325
Showing 1-10 of 38 results
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 February.
| 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
ORD-GPT
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
CHI-GPT
ORD-GPT
MDW-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 $69). Flying from Chicago to Gulfport in July is currently the most expensive (average of $161). 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?
How often are flights from Chicago to Gulfport delayed?
About 41% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 84 minutes.
What is the most punctual flight time for Chicago to Gulfport flights?
Historically, flights departing at night 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?
Monday 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 56% 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 February 14, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, 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.
Crew
8.5
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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 locationsOcean Springs
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Complete your trip
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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 February 14, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on February 14, 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 February 14, 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 February 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$334 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$365 | FlexibilityNo cancel fee | On-timeN/A |