$169+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Jul 6 — Jul 131
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Gulfport with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Gulfport
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Cheapest flights from Chicago to GulfportExplore the most affordable flight options available from Chicago to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 6, 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 6, 2026.
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/196:05 am
MDW
- GPT
1 stop6h 58m
Delta
Sat 8/224:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Deal found 6/4![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 6/1. 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.
Wed 9/95:30 am
ORD
- GPT
1 stop4h 05m
Delta
Sat 9/126:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 6/1![Delta logo]()
$281
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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
Tue 7/76:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/4![American Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 6/2. 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 9/64:39 pm
MDW
- GPT
1 stop4h 14m
Delta
Tue 9/1510:06 am
GPT
- MDW
1 stop6h 05m
Delta
Deal found 6/2![Delta logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 12/108:20 am
ORD
- GPT
1 stop7h 48m
American Airlines
Tue 12/154:38 pm
GPT
- ORD
1 stop7h 08m
American Airlines
Deal found 6/3![American Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/412:33 pm
ORD
- GPT
1 stop5h 31m
American Airlines
Fri 7/106:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/5![American Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 stops36h 38m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$314
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.
Mon 7/136:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Mon 7/206:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/6![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:30 pm
MDW
- GPT
1 stop4h 19m
Delta
Wed 9/3010:06 am
GPT
- MDW
2 stops8h 27m
Delta
Deal found 6/4![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/145:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Tue 7/215:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/5![Delta logo]()
$330
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/196:47 pm
ORD
- GPT
1 stop5h 12m
American Airlines
Tue 6/236:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 6/4![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/225:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Sat 7/254:00 pm
GPT
- MDW
1 stop6h 15m
Delta
Deal found 6/4![Delta logo]()
$340
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 6, 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 6, 2026.
This Delta deal was found by Cheapflights users on 6/2. 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 9/64:39 pm
MDW
- GPT
1 stop4h 14m
Delta
Tue 9/1510:06 am
GPT
- MDW
2 stops8h 27m
Delta
Deal found 6/2![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:30 am
ORD
- GPT
1 stop5h 54m
United Airlines
Thu 8/204:59 pm
GPT
- ORD
1 stop6h 27m
United Airlines
Deal found 6/5![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/225:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Sat 7/254:00 pm
GPT
- MDW
1 stop6h 15m
Delta
Deal found 6/4![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/145:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Mon 7/205:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/5![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:54 am
MDW
- GPT
1 stop4h 06m
Delta
Sun 9/610:01 am
GPT
- MDW
1 stop5h 37m
Delta
Deal found 6/4![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 39m
Delta
Deal found 6/5![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 6/1. 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.
Thu 6/256:35 am
ORD
- GPT
1 stop6h 32m
Delta
Mon 6/293:00 pm
GPT
- ORD
1 stop5h 32m
Delta
Deal found 6/1![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/237:30 am
ORD
- GPT
1 stop5h 55m
United Airlines
Fri 6/265:19 pm
GPT
- ORD
2 stops13h 01m
United Airlines
Deal found 6/5![United Airlines logo]()
$698
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:35 am
ORD
- GPT
2 stops11h 31m
Delta
Tue 9/1510:06 am
GPT
- ORD
2 stops10h 20m
Delta
Deal found 6/5![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/1312:27 pm
ORD
- GPT
2 stops9h 47m
Delta
Mon 7/205:57 pm
GPT
- ORD
1 stop5h 56m
Delta
Deal found 6/3![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/3![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 6/1. 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.
Fri 6/2612:50 pm
MDW
- GPT
1 stop4h 21m
Delta
Mon 6/293:00 pm
GPT
- MDW
1 stop7h 17m
Delta
Deal found 6/1![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 11/3010:35 am
MDW
- GPT
1 stop6h 42m
Delta
Thu 12/36:00 am
GPT
- MDW
1 stop5h 56m
Delta
Deal found 6/5![Delta logo]()
$566
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/166:35 am
ORD
- GPT
1 stop6h 30m
Delta
Sun 7/191:51 pm
GPT
- ORD
1 stop6h 42m
Delta
Deal found 6/4![Delta logo]()
$569
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 11/301:35 pm
ORD
- GPT
2 stops8h 32m
Delta
Thu 12/32:15 pm
GPT
- ORD
2 stops7h 19m
Delta
Deal found 6/5![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:29 pm
ORD
- GPT
2 stops9h 52m
Delta
Sun 9/66:30 am
GPT
- ORD
2 stops11h 33m
Delta
Deal found 6/4![Delta logo]()
$641
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated June 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated June 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/196:47 pm
ORD
- GPT
1 stop5h 12m
American Airlines
Tue 6/236:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 6/4![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 6/265:00 am
ORD
- GPT
1 stop5h 52m
American Airlines
Mon 6/296:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 6/4![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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
Tue 7/76:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/4![American Airlines logo]()
$286
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/412:33 pm
ORD
- GPT
1 stop5h 31m
American Airlines
Fri 7/106:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/5![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.
Mon 7/136:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Mon 7/206:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/6![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/136:35 am
ORD
- GPT
1 stop6h 30m
Delta
Mon 7/205:57 pm
GPT
- ORD
1 stop5h 56m
Delta
Deal found 6/3![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/145:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Tue 7/215:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/5![Delta logo]()
$330
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/145:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Mon 7/205:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/5![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/1712:41 pm
MDW
- GPT
1 stop4h 31m
Delta
Tue 7/215:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/3![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/206:00 am
MDW
- GPT
1 stop7h 05m
Delta
Mon 7/275:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/4![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/225:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Sat 7/254:00 pm
GPT
- MDW
1 stop6h 15m
Delta
Deal found 6/4![Delta logo]()
$340
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Sat 7/256:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/4![American Airlines logo]()
$361
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 6, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated June 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Mon 8/177:15 am
ORD
- GPT
1 stop9h 36m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$169
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/255:00 am
ORD
- GPT
1 stop5h 42m
American Airlines
Deal found 6/5![American Airlines logo]()
$181
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/2510:54 am
MDW
- GPT
1 stop6h 21m
Delta
Deal found 6/5![Delta logo]()
$186
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/257:05 am
ORD
- GPT
2 stops10h 10m
Delta
Deal found 6/5![Delta logo]()
$191
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/235:00 am
ORD
- GPT
1 stop5h 55m
American Airlines
Deal found 6/5![American Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/236:05 am
MDW
- GPT
2 stops12h 40m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/237:05 am
ORD
- GPT
2 stops11h 40m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/236:35 am
ORD
- GPT
1 stop6h 30m
Delta
Deal found 6/3![Delta logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:27 pm
MDW
- GPT
3 stops54h 18m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:50 pm
ORD
- GPT
3 stops52h 55m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/236:00 am
MDW
- GPT
1 stop7h 05m
Delta
Deal found 6/3![Delta logo]()
$250
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/248:03 am
ORD
- GPT
1 stop5h 02m
Delta
Deal found 6/3![Delta logo]()
$250
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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Delta) |
One-way from | $169 (Kiwi.com) |
Popular in | April |
Cheapest in | August |
Average price | $352 |
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 6, 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
Sun 9/6
4:39 pm-8:53 pm
1 stop4h 14m
Gulfport Biloxi Regional
Tue 9/15
10:06 am-6:33 pm
2 stops8h 27m
$300
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sat 8/15
7:30 am-1:24 pm
1 stop5h 54m
Gulfport Biloxi Regional
Thu 8/20
4:59 pm-11:26 pm
1 stop6h 27m
$300
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Wed 7/22
5:10 pm-10:14 pm
1 stop5h 04m
Gulfport Biloxi Regional
Sat 7/25
4:00 pm-10:15 pm
1 stop6h 15m
$340
Quickest round-trip
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Tue 7/14
5:10 pm-10:14 pm
1 stop5h 04m
Gulfport Biloxi Regional
Mon 7/20
5:57 pm-10:15 pm
1 stop4h 18m
$379
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 9/4
10:54 am-3:00 pm
1 stop4h 06m
Gulfport Biloxi Regional
Sun 9/6
10:01 am-3:38 pm
1 stop5h 37m
$404
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sat 8/15
11:22 am-8:53 pm
2 stops9h 31m
Gulfport Biloxi Regional
Thu 8/20
1:48 pm-8:27 pm
2 stops6h 39m
$410
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 6/25
6:35 am-1:07 pm
1 stop6h 32m
Gulfport Biloxi Regional
Mon 6/29
3:00 pm-8:32 pm
1 stop5h 32m
$419
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Wed 9/9
10:35 am-10:06 pm
2 stops11h 31m
Gulfport Biloxi Regional
Tue 9/15
10:06 am-8:26 pm
2 stops10h 20m
$510
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Mon 7/13
12:27 pm-10:14 pm
2 stops9h 47m
Gulfport Biloxi Regional
Mon 7/20
5:57 pm-11:53 pm
1 stop5h 56m
$519
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Mon 7/13
11:05 am-5:12 pm
1 stop6h 07m
Gulfport Biloxi Regional
Mon 7/20
5:57 pm-10:15 pm
1 stop4h 18m
$549
Showing 1-10 of 36 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
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, 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 59% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 119 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 66% 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 6, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from Chicago to Gulfport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Entertainment
7.8
Boarding
8.1
Food
7.2
Overall
7.9
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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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 June 6, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on June 6, 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 June 6, 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 June 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$471 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$416 | FlexibilityNo cancel fee | On-timeN/A |