$163+ 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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Jul 11 — Jul 181
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 June 11, 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 June 11, 2026.
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/1412:41 pm
MDW
- GPT
1 stop4h 31m
Delta
Sat 7/184:00 pm
GPT
- MDW
1 stop6h 15m
Delta
Deal found 6/9![Delta logo]()
$281
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/144:45 pm
ORD
- GPT
1 stop7h 11m
American Airlines
Sat 7/186:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/10![American Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/128:05 am
ORD
- GPT
1 stop4h 58m
Delta
Wed 8/191:48 pm
GPT
- ORD
2 stops8h 36m
Delta
Deal found 6/6![Delta logo]()
$286
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/305:59 am
ORD
- GPT
1 stop4h 53m
American Airlines
Tue 7/76:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/9![American Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/156:49 am
ORD
- GPT
1 stop6h 28m
American Airlines
Thu 8/206:34 pm
GPT
- ORD
1 stop5h 44m
American Airlines
Deal found 6/6![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/36:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Fri 7/106:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/6![American Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/249:54 am
ORD
- GPT
1 stop7h 21m
Delta
Mon 8/314:00 pm
GPT
- ORD
1 stop4h 55m
Delta
Deal found 6/8![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 6/10. 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 6/256:00 am
MDW
- GPT
1 stop7h 07m
Delta
Tue 7/215:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/10![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 6/10. 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 6/256:35 am
ORD
- GPT
1 stop6h 32m
Delta
Tue 7/215:57 pm
GPT
- ORD
1 stop5h 56m
Delta
Deal found 6/10![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 6/10. 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 6/305:00 am
ORD
- GPT
1 stop5h 52m
American Airlines
Wed 7/296:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/10![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/275:00 am
ORD
- GPT
1 stop5h 14m
American Airlines
Tue 7/286:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/9![American Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/155:13 pm
ORD
- GPT
1 stop25h 32m
Multiple Airlines
Thu 8/207:25 pm
GPT
- ORD
2 stops29h 17m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$318
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 June 11, 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 June 11, 2026.
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/1412:41 pm
MDW
- GPT
1 stop4h 31m
Delta
Sat 7/184:00 pm
GPT
- MDW
1 stop6h 15m
Delta
Deal found 6/9![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 10/277:45 am
ORD
- GPT
1 stop5h 41m
United Airlines
Sat 10/315:15 pm
GPT
- ORD
1 stop7h 00m
United Airlines
Deal found 6/10![United Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/128:05 am
ORD
- GPT
1 stop4h 58m
Delta
Wed 8/191:48 pm
GPT
- ORD
2 stops8h 36m
Delta
Deal found 6/6![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 6/10. 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 6/256:00 am
MDW
- GPT
1 stop7h 07m
Delta
Tue 7/215:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/10![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 6/10. 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 6/256:35 am
ORD
- GPT
1 stop6h 32m
Delta
Tue 7/211:51 pm
GPT
- ORD
2 stops8h 45m
Delta
Deal found 6/10![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:30 am
ORD
- GPT
1 stop4h 09m
Delta
Thu 12/32:15 pm
GPT
- ORD
1 stop4h 17m
Delta
Deal found 6/8![Delta logo]()
$361
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/49:54 am
MDW
- GPT
2 stops10h 47m
Delta
Fri 7/105:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/6![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/48:36 am
ORD
- GPT
2 stops12h 05m
Delta
Fri 7/1010:06 am
GPT
- ORD
2 stops11h 46m
Delta
Deal found 6/6![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 6/10. 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 6/256:35 am
ORD
- GPT
1 stop6h 32m
Delta
Wed 7/2210:06 am
GPT
- ORD
2 stops10h 50m
Delta
Deal found 6/10![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/10. 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.
Sat 8/154:39 pm
MDW
- GPT
1 stop4h 14m
Delta
Thu 8/206:30 am
GPT
- MDW
1 stop5h 21m
Delta
Deal found 6/10![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/1511:22 am
ORD
- GPT
2 stops9h 31m
Delta
Thu 8/201:48 pm
GPT
- ORD
2 stops6h 42m
Delta
Deal found 6/6![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/1411:30 am
ORD
- GPT
2 stops10h 44m
Delta
Sat 7/184:00 pm
GPT
- ORD
1 stop4h 33m
Delta
Deal found 6/9![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 6/10. 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 6/266:35 am
ORD
- GPT
1 stop6h 32m
Delta
Wed 7/2210:06 am
GPT
- ORD
2 stops10h 50m
Delta
Deal found 6/10![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/301:00 pm
MDW
- GPT
2 stops9h 07m
Delta
Thu 12/36:00 pm
GPT
- MDW
1 stop4h 10m
Delta
Deal found 6/8![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/1311:05 am
MDW
- GPT
1 stop6h 07m
Delta
Mon 7/205:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/8![Delta logo]()
$638
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/265:11 pm
MDW
- GPT
1 stop5h 06m
Delta
Mon 6/293:00 pm
GPT
- MDW
1 stop7h 17m
Delta
Deal found 6/7![Delta logo]()
$729
This Delta deal was found by Cheapflights users on 6/10. 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 7/166:00 am
MDW
- GPT
1 stop7h 05m
Delta
Sun 7/195:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/10![Delta logo]()
$743
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated June 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/2312:00 pm
ORD
- GPT
1 stop6h 10m
American Airlines
Sat 6/276:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 6/8![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 6/10. 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 6/256:00 am
MDW
- GPT
1 stop7h 07m
Delta
Tue 7/215:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/10![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 6/10. 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 6/256:35 am
ORD
- GPT
1 stop6h 32m
Delta
Tue 7/215:57 pm
GPT
- ORD
1 stop5h 56m
Delta
Deal found 6/10![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 6/10. 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 6/266:00 am
MDW
- GPT
1 stop7h 07m
Delta
Wed 7/225:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/10![Delta logo]()
$440
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/275:00 am
ORD
- GPT
1 stop5h 14m
American Airlines
Tue 7/286:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/9![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/305:59 am
ORD
- GPT
1 stop4h 53m
American Airlines
Tue 7/76:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/9![American Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/10. 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 6/305:00 am
ORD
- GPT
1 stop5h 52m
American Airlines
Wed 7/296:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/10![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/36:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Fri 7/106:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/6![American Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/49:54 am
MDW
- GPT
2 stops10h 47m
Delta
Fri 7/105:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/6![Delta logo]()
$365
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/135:45 pm
ORD
- GPT
1 stop6h 11m
American Airlines
Mon 7/206:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/8![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/1412:41 pm
MDW
- GPT
1 stop4h 31m
Delta
Sat 7/184:00 pm
GPT
- MDW
1 stop6h 15m
Delta
Deal found 6/9![Delta logo]()
$281
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/144:45 pm
ORD
- GPT
1 stop7h 11m
American Airlines
Sat 7/186:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/10![American Airlines logo]()
$281
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 June 11, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/198:05 am
ORD
- GPT
2 stops23h 36m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 6/10. 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 7/215:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Deal found 6/10![Delta logo]()
$181
This Delta deal was found by Cheapflights users on 6/10. 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 7/216:35 am
ORD
- GPT
1 stop6h 30m
Delta
Deal found 6/10![Delta logo]()
$181
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 12/45:30 am
ORD
- GPT
1 stop4h 09m
Delta
Deal found 6/9![Delta logo]()
$184
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/1412:46 pm
MDW
- GPT
1 stop4h 29m
Delta
Deal found 6/8![Delta logo]()
$196
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/149:54 am
ORD
- GPT
1 stop7h 21m
Delta
Deal found 6/8![Delta logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/168:20 pm
MDW
- GPT
2 stops20h 31m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 12/31:05 pm
MDW
- GPT
1 stop4h 12m
Delta
Deal found 6/9![Delta logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/1512:44 am
ORD
- GPT
2 stops30h 57m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$213
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/31:49 pm
MDW
- GPT
2 stops24h 17m
Delta
Deal found 6/9![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 12/41:05 pm
MDW
- GPT
1 stop4h 12m
Delta
Deal found 6/9![Delta logo]()
$240
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 12/36:00 am
ORD
- GPT
2 stops11h 17m
Delta
Deal found 6/9![Delta logo]()
$245
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 June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Delta) |
One-way from | $163 (Kiwi.com) |
Popular in | April |
Cheapest in | August |
Average price | $358 |
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 June 11, 2026.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Tue 7/14
12:41 pm-5:12 pm
1 stop4h 31m
Gulfport Biloxi Regional
Sat 7/18
4:00 pm-10:15 pm
1 stop6h 15m
$281
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Wed 8/12
8:05 am-1:03 pm
1 stop4h 58m
Gulfport Biloxi Regional
Wed 8/19
1:48 pm-10:24 pm
2 stops8h 36m
$286
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Thu 6/25
6:00 am-1:07 pm
1 stop7h 07m
Gulfport Biloxi Regional
Tue 7/21
5:57 pm-10:15 pm
1 stop4h 18m
$310
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 6/25
6:35 am-1:07 pm
1 stop6h 32m
Gulfport Biloxi Regional
Tue 7/21
1:51 pm-10:36 pm
2 stops8h 45m
$354
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 10/27
7:45 am-1:26 pm
1 stop5h 41m
Gulfport Biloxi Regional
Sat 10/31
5:15 pm-12:15 am
1 stop7h 00m
$361
Quickest round-trip
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Mon 11/30
5:30 am-9:39 am
1 stop4h 09m
Gulfport Biloxi Regional
Thu 12/3
2:15 pm-6:32 pm
1 stop4h 17m
$361
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Sat 7/4
9:54 am-8:41 pm
2 stops10h 47m
Gulfport Biloxi Regional
Fri 7/10
5:57 pm-10:15 pm
1 stop4h 18m
$365
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sat 7/4
8:36 am-8:41 pm
2 stops12h 05m
Gulfport Biloxi Regional
Fri 7/10
10:06 am-9:52 pm
2 stops11h 46m
$370
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 6/25
6:35 am-1:07 pm
1 stop6h 32m
Gulfport Biloxi Regional
Wed 7/22
10:06 am-8:56 pm
2 stops10h 50m
$398
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Sat 8/15
4:39 pm-8:53 pm
1 stop4h 14m
Gulfport Biloxi Regional
Thu 8/20
6:30 am-11:51 am
1 stop5h 21m
$419
Showing 1-10 of 38 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 June.
| 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, January is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $248). Flying from Chicago to Gulfport in May is currently the most expensive (average of $398). 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 56% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 121 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 Tuesday 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 June 11, 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.
Crew
8.5
Overall
7.9
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Comfort
7.8
Entertainment
7.8
Boarding
8.1
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
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Chicago and Gulfport flights
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Popular flight searches
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Top 2 airlines flying from Chicago to Gulfport
Discover the top 2 airlines that operate flights from Chicago to Gulfport. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$474 | FlexibilityNo cancel fee | On-time71% |