$119+ Cheap flights from Gulfport (GPT) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Sep 8 — Sep 151
Round-trip
1 adult, Economy
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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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Cheapest flights from Gulfport to ChicagoExplore the most affordable flight options available from Gulfport to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 2026.
Explore the most affordable flight options available from Gulfport to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 2026.
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/511:12 am -
1 stop8h 30m
Tue 9/85:00 am -
1 stop5h 41m
Deal found 8/5![American Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 8/6. 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 10/76:26 am -
2 stops6h 33m
Sat 10/108:05 am -
1 stop6h 16m
Deal found 8/6![Delta logo]()
$306
This American Airlines deal was found by Cheapflights users on 8/4. 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 9/46:34 pm -
1 stop5h 44m
Sat 9/511:53 am -
1 stop5h 27m
Deal found 8/4![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 8/9. 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 11/126:25 am -
1 stop5h 40m
Mon 11/166:00 am -
1 stop7h 08m
Deal found 8/9![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Thu 8/276:34 pm -
1 stop5h 44m
Sun 8/305:00 am -
1 stop5h 41m
Deal found 8/4![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/7. 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 11/136:04 pm -
1 stop4h 52m
Mon 11/161:22 pm -
2 stops8h 40m
Deal found 8/7![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/7. 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 11/1310:04 am -
2 stops10h 21m
Sun 11/156:45 am -
1 stop6h 23m
Deal found 8/7![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/7. 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 11/1310:04 am -
2 stops10h 21m
Mon 11/1611:29 am -
2 stops10h 33m
Deal found 8/7![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 8/7. 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 11/136:04 pm -
1 stop4h 52m
Sun 11/156:00 am -
1 stop7h 08m
Deal found 8/7![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:00 pm -
1 stop7h 32m
Wed 8/2610:40 am -
1 stop5h 32m
Deal found 8/7![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Fri 10/26:46 pm -
2 stops17h 05m
Sun 10/186:05 am -
1 stop13h 00m
Deal found 8/5![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 8/8. 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.
Thu 11/126:25 am -
1 stop5h 40m
Sun 11/151:22 pm -
2 stops8h 40m
Deal found 8/8![Delta logo]()
$354
Best flights from Gulfport to ChicagoDiscover carefully curated flight deals from Gulfport to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
Discover carefully curated flight deals from Gulfport to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
This Delta deal was found by Cheapflights users on 8/6. 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 10/76:05 pm -
1 stop5h 47m
Sat 10/108:05 am -
1 stop6h 16m
Deal found 8/6![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/8. 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.
Sat 1/2310:30 am -
2 stops11h 05m
Wed 2/39:30 am -
1 stop4h 05m
Deal found 8/8![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 8/8. 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 1/252:15 pm -
1 stop4h 17m
Sat 1/306:00 am -
2 stops7h 35m
Deal found 8/8![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 12/66:04 pm -
1 stop4h 52m
Mon 12/145:09 pm -
1 stop4h 53m
Deal found 8/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/7. 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 11/131:53 pm -
1 stop5h 09m
Mon 11/168:04 am -
1 stop5h 04m
Deal found 8/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/8. 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.
Thu 11/126:04 pm -
1 stop5h 55m
Mon 11/166:45 am -
1 stop6h 23m
Deal found 8/8![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/8. 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.
Thu 11/126:25 am -
1 stop5h 40m
Mon 11/161:22 pm -
2 stops8h 40m
Deal found 8/8![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/8. 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 11/136:04 pm -
1 stop4h 52m
Mon 11/161:22 pm -
2 stops8h 40m
Deal found 8/8![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/7. 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 11/136:04 pm -
1 stop4h 52m
Sun 11/156:00 am -
1 stop7h 08m
Deal found 8/7![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/8. 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.
Thu 11/126:25 am -
1 stop5h 40m
Sun 11/156:00 am -
1 stop7h 08m
Deal found 8/8![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/7. 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.
Sat 8/224:00 pm -
1 stop4h 55m
Wed 8/261:59 pm -
2 stops8h 22m
Deal found 8/7![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 8/4. 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 10/156:26 am -
1 stop5h 24m
Sun 10/185:15 pm -
1 stop5h 01m
Deal found 8/4![Delta logo]()
$459
Last-minute flights from Gulfport to ChicagoDiscover last-minute flight deals from Gulfport to Chicago. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Chicago. Data last updated August 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/7. 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.
Wed 8/126:30 am -
1 stop5h 21m
Sat 8/154:39 pm -
1 stop4h 14m
Deal found 8/7![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 8/7. 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.
Wed 8/126:00 pm -
1 stop5h 57m
Sat 8/158:05 am -
1 stop6h 55m
Deal found 8/7![Delta logo]()
$401
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Thu 8/137:40 am -
1 stop6h 42m
Fri 8/2110:45 am -
1 stop7h 16m
Deal found 8/4![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 8/6. 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.
Thu 8/1310:01 am -
1 stop6h 14m
Sat 8/154:39 pm -
1 stop4h 14m
Deal found 8/6![Delta logo]()
$405
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:00 pm -
1 stop7h 32m
Wed 8/2610:40 am -
1 stop5h 32m
Deal found 8/7![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 8/7. 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.
Sat 8/224:00 pm -
1 stop4h 55m
Wed 8/261:59 pm -
2 stops8h 22m
Deal found 8/7![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/4. 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.
Thu 8/276:34 pm -
1 stop5h 44m
Sun 8/305:00 am -
1 stop5h 41m
Deal found 8/4![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/4. 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 9/46:34 pm -
1 stop5h 44m
Sat 9/511:53 am -
1 stop5h 27m
Deal found 8/4![American Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/511:12 am -
1 stop8h 30m
Tue 9/85:00 am -
1 stop5h 41m
Deal found 8/5![American Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/145:42 pm -
1 stop6h 17m
Thu 9/175:00 am -
1 stop5h 40m
Deal found 8/6![American Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Mon 9/146:22 pm -
1 stop5h 52m
Fri 9/186:29 am -
1 stop6h 43m
Deal found 8/5![American Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Mon 9/149:36 am -
1 stop20h 02m
Thu 9/177:11 am -
2 stops25h 40m
Deal found 8/5![Multiple Airlines logo]()
$393
One-way flights from Gulfport to ChicagoSearch for one-way flight options from Gulfport to Chicago. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
Search for one-way flight options from Gulfport to Chicago. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Mon 9/146:46 pm -
2 stops44h 34m
Deal found 8/6![Multiple Airlines logo]()
$119
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:08 am -
1 stop5h 17m
Deal found 8/7![United Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:31 pm -
2 stops26h 37m
Deal found 8/4![Multiple Airlines logo]()
$175
This Delta deal was found by Cheapflights users on 8/4. 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 8/294:00 pm -
1 stop6h 36m
Deal found 8/4![Delta logo]()
$178
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/145:42 pm -
1 stop6h 17m
Deal found 8/6![American Airlines logo]()
$178
This Delta deal was found by Cheapflights users on 8/5. 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 10/66:26 am -
2 stops6h 21m
Deal found 8/5![Delta logo]()
$183
This Delta deal was found by Cheapflights users on 8/5. 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 10/66:26 am -
2 stops6h 33m
Deal found 8/5![Delta logo]()
$183
This Delta deal was found by Cheapflights users on 8/7. 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.
Sun 9/610:01 am -
1 stop5h 43m
Deal found 8/7![Delta logo]()
$190
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:59 pm -
1 stop8h 00m
Deal found 8/4![United Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Fri 8/215:31 pm -
2 stops19h 19m
Deal found 8/6![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Fri 8/215:31 pm -
2 stops29h 16m
Deal found 8/6![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Mon 8/245:31 pm -
2 stops43h 19m
Deal found 8/6![Multiple Airlines logo]()
$240
Find flight deals from Gulfport to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Gulfport (GPT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Delta) |
One-way from | $119 (Kiwi.com) |
Popular in | April |
Cheapest in | November |
Average price | $323 |
Cheapflights Fare Finder
Customize your flight search to find flights from Gulfport to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 9, 2026.
Use the filters below to find and compare flights from Gulfport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Wed 10/7
6:05 pm-11:52 pm
1 stop5h 47m
Chicago O'Hare Intl
Sat 10/10
8:05 am-2:21 pm
1 stop6h 16m
$301
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Sat 1/23
10:30 am-9:35 pm
2 stops11h 05m
Chicago O'Hare Intl
Wed 2/3
9:30 am-1:35 pm
1 stop4h 05m
$306
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Mon 1/25
2:15 pm-6:32 pm
1 stop4h 17m
Chicago O'Hare Intl
Sat 1/30
6:00 am-1:35 pm
2 stops7h 35m
$315
Quickest round-trip
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Sun 12/6
6:04 pm-10:56 pm
1 stop4h 52m
Chicago Midway
Mon 12/14
5:09 pm-10:02 pm
1 stop4h 53m
$319
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Fri 11/13
1:53 pm-7:02 pm
1 stop5h 09m
Chicago O'Hare Intl
Mon 11/16
8:04 am-1:08 pm
1 stop5h 04m
$319
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Thu 11/12
6:04 pm-11:59 pm
1 stop5h 55m
Chicago O'Hare Intl
Mon 11/16
6:45 am-1:08 pm
1 stop6h 23m
$319
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Thu 11/12
6:25 am-12:05 pm
1 stop5h 40m
Chicago Midway
Mon 11/16
1:22 pm-10:02 pm
2 stops8h 40m
$324
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Fri 11/13
6:04 pm-10:56 pm
1 stop4h 52m
Chicago Midway
Mon 11/16
1:22 pm-10:02 pm
2 stops8h 40m
$324
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Fri 11/13
6:04 pm-10:56 pm
1 stop4h 52m
Chicago Midway
Sun 11/15
6:00 am-1:08 pm
1 stop7h 08m
$349
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Thu 11/12
6:25 am-12:05 pm
1 stop5h 40m
Chicago Midway
Sun 11/15
6:00 am-1:08 pm
1 stop7h 08m
$349
Showing 1-10 of 31 resultsSorted by cheapest first
Compare providers for flights from Gulfport to Chicago
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 Gulfport to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Gulfport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Gulfport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Gulfport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Gulfport-Chicago 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 Gulfport-Chicago 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 Gulfport to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Gulfport with our price prediction graph.
GPT-CHI
GPT-ORD
GPT-MDW
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 Gulfport to Chicago
GPT-CHI
GPT-ORD
GPT-MDW
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 9, 2026.
See what other customers who have flown with Delta and American Airlines from Gulfport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Comfort
7.8
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Gulfport to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Gulfport and Chicago flights
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Top 2 airlines flying from Gulfport to Chicago
Discover the top 2 airlines that operate flights from Gulfport to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$319 | Average$587 | FlexibilityNo cancel fee | On-timeN/A |