$187+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Mar 5 — Mar 121
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 3, 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 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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
Sun 3/157:20 pm
GPT
- ORD
1 stop20h 08m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/1510:19 am
ORD
- GPT
1 stop22h 41m
Multiple Airlines
Thu 2/197:20 pm
GPT
- ORD
1 stop24h 27m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/88:00 am
MDW
- GPT
1 stop10h 40m
Multiple Airlines
Thu 3/127:20 pm
GPT
- MDW
1 stop28h 31m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/2. 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
Sun 3/157:20 pm
GPT
- MDW
1 stop19h 01m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/128:05 am
ORD
- GPT
1 stop10h 35m
Multiple Airlines
Sun 3/157:20 pm
GPT
- ORD
1 stop20h 08m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/157:30 am
MDW
- GPT
1 stop11h 10m
Multiple Airlines
Thu 2/197:20 pm
GPT
- MDW
1 stop19h 06m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 5/146:31 am
ORD
- GPT
2 stops12h 39m
Multiple Airlines
Sun 5/177:50 pm
GPT
- ORD
1 stop12h 09m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 2/2. 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 3/210:49 am
MDW
- GPT
1 stop6h 26m
Delta
Mon 3/95:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/2![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 2/1. 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 3/75:25 am
ORD
- GPT
1 stop4h 15m
Delta
Wed 3/112:44 pm
GPT
- ORD
1 stop6h 26m
Delta
Deal found 2/1![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/1510:49 am
ORD
- GPT
1 stop8h 14m
American Airlines
Sat 2/214:29 pm
GPT
- ORD
1 stop7h 29m
American Airlines
Deal found 2/1![American Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/16:00 am
MDW
- GPT
2 stops27h 00m
Multiple Airlines
Sun 3/87:20 pm
GPT
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/88:00 am
MDW
- GPT
1 stop10h 40m
Multiple Airlines
Fri 3/136:54 pm
GPT
- MDW
2 stops51h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$286
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 3, 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 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/1510:19 am
ORD
- GPT
1 stop22h 41m
Multiple Airlines
Thu 2/197:20 pm
GPT
- ORD
1 stop24h 27m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 2/2. 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 3/1711:10 am
ORD
- GPT
1 stop6h 01m
Delta
Tue 3/245:57 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 2/2![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/34:04 pm
ORD
- GPT
2 stops7h 45m
American Airlines
Tue 3/106:31 am
GPT
- ORD
1 stop6h 04m
American Airlines
Deal found 2/1![American Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 2/2. 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
Sun 3/157:20 pm
GPT
- MDW
1 stop19h 01m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 2/1. 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 3/75:25 am
ORD
- GPT
1 stop4h 15m
Delta
Wed 3/112:44 pm
GPT
- ORD
1 stop6h 26m
Delta
Deal found 2/1![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 2/1. 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
Sun 3/157:20 pm
GPT
- ORD
2 stops15h 57m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/157:30 am
MDW
- GPT
1 stop11h 10m
Multiple Airlines
Thu 2/197:20 pm
GPT
- MDW
1 stop19h 06m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/128:10 am
ORD
- GPT
1 stop7h 49m
American Airlines
Mon 3/164:29 pm
GPT
- ORD
1 stop7h 37m
American Airlines
Deal found 2/1![American Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/128:05 am
ORD
- GPT
1 stop10h 35m
Multiple Airlines
Sun 3/157:20 pm
GPT
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 2/2. 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 3/179:50 am
ORD
- GPT
1 stop7h 21m
Delta
Sat 3/213:00 pm
GPT
- ORD
1 stop5h 02m
Delta
Deal found 2/2![Delta logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/16:00 am
MDW
- GPT
2 stops27h 00m
Multiple Airlines
Sun 3/87:20 pm
GPT
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 2/2. 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 3/189:35 am
ORD
- GPT
2 stops12h 40m
Delta
Tue 3/242:44 pm
GPT
- ORD
1 stop6h 26m
Delta
Deal found 2/2![Delta logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 5/1410:25 am
ORD
- GPT
1 stop8h 45m
Multiple Airlines
Sun 5/177:50 pm
GPT
- ORD
1 stop12h 09m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 2/2. 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 3/189:35 am
MDW
- GPT
2 stops12h 40m
Delta
Tue 3/245:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/2![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 2/2. 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 3/1712:47 pm
MDW
- GPT
1 stop4h 24m
Delta
Mon 3/235:57 pm
GPT
- MDW
2 stops14h 56m
Delta
Deal found 2/2![Delta logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/186:10 pm
ORD
- GPT
2 stops24h 30m
Multiple Airlines
Mon 3/236:54 pm
GPT
- ORD
1 stop19h 04m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 2/2. 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 3/136:07 pm
MDW
- GPT
1 stop14h 43m
Delta
Tue 3/245:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/2![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 2/2. 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 3/169:35 am
MDW
- GPT
2 stops12h 40m
Delta
Tue 3/245:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/2![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 2/2. 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 3/1712:47 pm
MDW
- GPT
1 stop4h 24m
Delta
Sat 3/213:00 pm
GPT
- MDW
1 stop18h 56m
Delta
Deal found 2/2![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 2/2. 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 3/156:00 am
MDW
- GPT
1 stop11h 11m
Delta
Tue 3/245:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/2![Delta logo]()
$431
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated February 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/1510:19 am
ORD
- GPT
1 stop22h 41m
Multiple Airlines
Thu 2/197:20 pm
GPT
- ORD
1 stop24h 27m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/157:30 am
MDW
- GPT
1 stop11h 10m
Multiple Airlines
Thu 2/197:20 pm
GPT
- MDW
1 stop19h 06m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/1510:49 am
ORD
- GPT
1 stop8h 14m
American Airlines
Sat 2/214:29 pm
GPT
- ORD
1 stop7h 29m
American Airlines
Deal found 2/1![American Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/16:00 am
MDW
- GPT
2 stops27h 00m
Multiple Airlines
Sun 3/87:20 pm
GPT
- MDW
1 stop17h 48m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 2/2. 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 3/210:49 am
MDW
- GPT
1 stop6h 26m
Delta
Mon 3/95:57 pm
GPT
- MDW
1 stop4h 34m
Delta
Deal found 2/2![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 2/1. 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 3/75:25 am
ORD
- GPT
1 stop4h 15m
Delta
Wed 3/112:44 pm
GPT
- ORD
1 stop6h 26m
Delta
Deal found 2/1![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/88:00 am
MDW
- GPT
1 stop10h 40m
Multiple Airlines
Thu 3/127:20 pm
GPT
- MDW
1 stop28h 31m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/88:00 am
MDW
- GPT
1 stop10h 40m
Multiple Airlines
Fri 3/136:54 pm
GPT
- MDW
2 stops51h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 2/1. 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
Sun 3/157:20 pm
GPT
- ORD
1 stop20h 08m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 2/2. 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
Sun 3/157:20 pm
GPT
- MDW
1 stop19h 01m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/128:05 am
ORD
- GPT
1 stop10h 35m
Multiple Airlines
Sun 3/157:20 pm
GPT
- ORD
1 stop20h 08m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 2/2. 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 3/175:59 pm
ORD
- GPT
1 stop4h 16m
Delta
Mon 3/235:57 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 2/2![Delta logo]()
$294
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 3, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/2112:44 pm
ORD
- GPT
1 stop29h 56m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/1511:25 am
ORD
- GPT
1 stop21h 35m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/219:15 am
MDW
- GPT
2 stops33h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/87:20 am
ORD
- GPT
2 stops11h 20m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 2/2. 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 2/2312:45 pm
MDW
- GPT
1 stop4h 30m
Delta
Deal found 2/2![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 2/2. 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 3/16:45 am
ORD
- GPT
1 stop7h 21m
Delta
Deal found 2/2![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 2/2. 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 2/214:13 pm
MDW
- GPT
1 stop5h 41m
Delta
Deal found 2/2![Delta logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sat 2/79:38 am
MDW
- GPT
2 stops33h 02m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/1![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/85:13 pm
MDW
- GPT
2 stops25h 01m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 2/1. 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 2/74:30 pm
MDW
- GPT
1 stop5h 23m
Delta
Deal found 2/1![Delta logo]()
$388
This Delta deal was found by Cheapflights users on 2/1. 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 2/84:30 pm
MDW
- GPT
1 stop5h 23m
Delta
Deal found 2/1![Delta logo]()
$390
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 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Kiwi.com) |
One-way from | $187 (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 3, 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 2/15
10:19 am-9:00 am
1 stop22h 41m
Gulfport Biloxi Regional
Thu 2/19
7:20 pm-7:47 pm
1 stop24h 27m
$241
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Thu 3/12
9:10 am-6:40 pm
1 stop9h 30m
Gulfport Biloxi Regional
Sun 3/15
7:20 pm-2:21 pm
1 stop19h 01m
$249
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Wed 3/11
4:18 pm-6:40 pm
1 stop26h 22m
Gulfport Biloxi Regional
Sun 3/15
7:20 pm-11:17 am
2 stops15h 57m
$252
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Sun 2/15
7:30 am-6:40 pm
1 stop11h 10m
Gulfport Biloxi Regional
Thu 2/19
7:20 pm-2:26 pm
1 stop19h 06m
$259
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 3/17
11:10 am-5:11 pm
1 stop6h 01m
Gulfport Biloxi Regional
Tue 3/24
5:57 pm-11:54 pm
1 stop5h 57m
$269
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sat 3/7
5:25 am-9:40 am
1 stop4h 15m
Gulfport Biloxi Regional
Wed 3/11
2:44 pm-9:10 pm
1 stop6h 26m
$269
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 3/12
8:05 am-6:40 pm
1 stop10h 35m
Gulfport Biloxi Regional
Sun 3/15
7:20 pm-10:52 am
2 stops15h 32m
$273
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Sun 3/1
6:00 am-9:00 am
2 stops27h 00m
Gulfport Biloxi Regional
Sun 3/8
7:20 pm-1:08 pm
1 stop17h 48m
$284
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 5/14
10:25 am-7:10 pm
1 stop8h 45m
Gulfport Biloxi Regional
Sun 5/17
7:50 pm-7:59 am
1 stop12h 09m
$300
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 3/3
4:04 pm-11:49 pm
2 stops7h 45m
Gulfport Biloxi Regional
Tue 3/10
6:31 am-12:35 pm
1 stop6h 04m
$309
Showing 1-10 of 34 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, June is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $80). 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 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 3, 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.
Overall
7.9
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Food
7.2
Crew
8.5
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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Alternative routes for Chicago to Gulfport
See prices for flight routes from nearby airports that may be better suited for you.
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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$334 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$343 | FlexibilityNo cancel fee | On-timeN/A |