$178+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Jul 24 — Jul 311
Round-trip
1 adult, Economy
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Find cheap flights from Gulfport to Chicago 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 Gulfport to Chicago
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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 June 24, 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 June 24, 2026.
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/186:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Wed 8/266:05 am
MDW
- GPT
1 stop6h 58m
Delta
Deal found 6/23![Delta logo]()
$291
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/181:50 pm
GPT
- ORD
1 stop8h 07m
American Airlines
Wed 8/267:30 am
ORD
- GPT
1 stop5h 47m
American Airlines
Deal found 6/23![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/181:48 pm
GPT
- ORD
1 stop7h 07m
Delta
Wed 8/2611:30 am
ORD
- GPT
2 stops10h 51m
Delta
Deal found 6/23![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/14:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Tue 9/84:30 pm
MDW
- GPT
1 stop4h 19m
Delta
Deal found 6/24![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Thu 8/274:59 pm
GPT
- ORD
1 stop8h 00m
United Airlines
Sat 8/297:30 am
ORD
- GPT
1 stop5h 54m
United Airlines
Deal found 6/22![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/156:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Mon 7/206:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Deal found 6/23![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/216:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Mon 8/241:25 pm
MDW
- GPT
2 stops8h 56m
Delta
Deal found 6/21![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/216:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Mon 8/241:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Deal found 6/21![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/46:30 am
GPT
- MDW
1 stop5h 21m
Delta
Sat 8/84:39 pm
MDW
- GPT
1 stop4h 14m
Delta
Deal found 6/22![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/2710:01 am
GPT
- ORD
2 stops8h 28m
Delta
Sat 8/298:05 am
ORD
- GPT
1 stop6h 55m
Delta
Deal found 6/23![Delta logo]()
$330
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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
GPT
- ORD
1 stop5h 44m
American Airlines
Sun 8/305:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Deal found 6/21![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/410:01 am
GPT
- ORD
2 stops12h 23m
Delta
Sat 8/811:22 am
ORD
- GPT
2 stops9h 31m
Delta
Deal found 6/22![Delta logo]()
$335
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 June 24, 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 June 24, 2026.
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/16:30 am
GPT
- ORD
1 stop7h 39m
Delta
Tue 9/88:55 am
ORD
- GPT
2 stops11h 54m
Delta
Deal found 6/24![Delta logo]()
$296
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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
GPT
- ORD
1 stop5h 44m
American Airlines
Sun 8/305:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Deal found 6/19![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 10/245:14 pm
GPT
- ORD
1 stop6h 13m
United Airlines
Wed 10/289:00 am
ORD
- GPT
1 stop7h 07m
United Airlines
Deal found 6/23![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/111:48 pm
GPT
- ORD
2 stops6h 42m
Delta
Tue 8/181:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Deal found 6/22![Delta logo]()
$301
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/156:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Mon 7/206:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Deal found 6/19![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/14:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Tue 9/89:29 am
MDW
- GPT
2 stops11h 20m
Delta
Deal found 6/24![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 12/186:00 pm
GPT
- ORD
1 stop5h 50m
Delta
Sun 12/275:55 pm
ORD
- GPT
1 stop4h 12m
Delta
Deal found 6/23![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/216:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Mon 8/241:25 pm
MDW
- GPT
2 stops8h 56m
Delta
Deal found 6/21![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 9/14:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Sat 9/54:39 pm
MDW
- GPT
1 stop4h 14m
Delta
Deal found 6/19![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 11/236:00 pm
GPT
- ORD
1 stop5h 50m
Delta
Wed 11/255:30 am
ORD
- GPT
1 stop4h 09m
Delta
Deal found 6/19![Delta logo]()
$376
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/276:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Sat 8/294:39 pm
MDW
- GPT
1 stop4h 14m
Delta
Deal found 6/22![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/276:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Sun 8/306:05 am
MDW
- GPT
1 stop6h 58m
Delta
Deal found 6/22![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/245:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Tue 8/41:25 pm
MDW
- GPT
2 stops8h 56m
Delta
Deal found 6/22![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/2610:01 am
GPT
- MDW
2 stops8h 32m
Delta
Mon 8/314:39 pm
MDW
- GPT
1 stop5h 42m
Delta
Deal found 6/20![Delta logo]()
$463
Last-minute flights from Gulfport to ChicagoDiscover last-minute flight deals from Gulfport to Chicago. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Chicago. Data last updated June 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 6/231:53 pm
GPT
- ORD
1 stop6h 39m
Delta
Sat 7/43:25 pm
ORD
- GPT
1 stop5h 16m
Delta
Deal found 6/20![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 6/245:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Sat 7/44:25 pm
MDW
- GPT
1 stop4h 16m
Delta
Deal found 6/20![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 6/246:30 am
GPT
- ORD
2 stops10h 15m
Delta
Sat 7/48:36 am
ORD
- GPT
2 stops12h 05m
Delta
Deal found 6/20![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/255:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Tue 7/712:41 pm
MDW
- GPT
1 stop4h 31m
Delta
Deal found 6/22![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 6/276:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Sat 9/123:50 pm
ORD
- GPT
1 stop7h 34m
American Airlines
Deal found 6/20![American Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 6/296:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Tue 7/284:45 pm
ORD
- GPT
1 stop7h 11m
American Airlines
Deal found 6/20![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 6/296:30 am
GPT
- ORD
2 stops12h 41m
Delta
Tue 7/288:03 am
ORD
- GPT
1 stop5h 02m
Delta
Deal found 6/20![Delta logo]()
$350
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/71:51 pm
GPT
- ORD
1 stop6h 42m
Delta
Sat 7/119:00 am
ORD
- GPT
1 stop5h 50m
Delta
Deal found 6/22![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/85:57 pm
GPT
- ORD
1 stop5h 56m
Delta
Wed 7/156:35 am
ORD
- GPT
1 stop6h 30m
Delta
Deal found 6/20![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/156:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Mon 7/206:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Deal found 6/23![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/246:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Tue 8/45:07 am
ORD
- GPT
1 stop5h 04m
American Airlines
Deal found 6/22![American Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/245:57 pm
GPT
- ORD
1 stop5h 56m
Delta
Tue 8/41:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Deal found 6/22![Delta logo]()
$364
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 June 24, 2026.
Search for one-way flight options from Gulfport to Chicago. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This Sun Country Air deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:00 am
GPT
- ORD
1 stop24h 48m
Sun Country Air
Deal found 6/22![Sun Country Air logo]()
$178
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/116:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Deal found 6/22![Delta logo]()
$181
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/111:50 pm
GPT
- ORD
1 stop5h 56m
American Airlines
Deal found 6/22![American Airlines logo]()
$181
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/111:48 pm
GPT
- ORD
2 stops8h 36m
Delta
Deal found 6/22![Delta logo]()
$186
This KAYAK deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 6/21![American Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/27:25 pm
GPT
- ORD
1 stop27h 54m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/97:25 pm
GPT
- MDW
2 stops26h 38m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 6/303:00 pm
GPT
- MDW
1 stop7h 17m
Delta
Deal found 6/24![Delta logo]()
$257
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 6/3010:39 am
GPT
- ORD
1 stop6h 04m
American Airlines
Deal found 6/23![American Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/16:30 am
GPT
- ORD
2 stops12h 41m
Delta
Deal found 6/23![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/302:00 pm
GPT
- ORD
1 stop7h 40m
United Airlines
Deal found 6/22![United Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/85:57 pm
GPT
- MDW
1 stop4h 18m
Delta
Deal found 6/19![Delta logo]()
$321
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 June 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Delta) |
One-way from | $178 (Sun Country Air) |
Popular in | April |
Cheapest in | November |
Average price | $432 |
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 June 24, 2026.
Use the filters below to find and compare flights from Gulfport to Chicago that are best for you.
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Cheapest round-trip
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Tue 9/1
6:30 am-2:09 pm
1 stop7h 39m
Chicago O'Hare Intl
Tue 9/8
8:55 am-8:49 pm
2 stops11h 54m
$296
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Tue 8/11
1:48 pm-8:30 pm
2 stops6h 42m
Chicago O'Hare Intl
Tue 8/18
1:59 pm-10:21 pm
2 stops8h 22m
$301
GulfportChicago
GPT - MDW
GPTMDW
Gulfport Biloxi Regional
Tue 9/1
4:00 pm-10:36 pm
1 stop6h 36m
Chicago Midway
Tue 9/8
9:29 am-8:49 pm
2 stops11h 20m
$305
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Thu 8/27
6:34 pm-12:18 am
1 stop5h 44m
Chicago O'Hare Intl
Sun 8/30
5:00 am-10:41 am
1 stop5h 41m
$309
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Wed 7/15
6:35 pm-12:01 am
1 stop5h 26m
Chicago O'Hare Intl
Mon 7/20
6:47 pm-11:56 pm
1 stop5h 09m
$309
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Fri 12/18
6:00 pm-11:50 pm
1 stop5h 50m
Chicago O'Hare Intl
Sun 12/27
5:55 pm-10:07 pm
1 stop4h 12m
$309
GulfportChicago
GPT - MDW
GPTMDW
Gulfport Biloxi Regional
Fri 8/21
6:00 pm-10:36 pm
1 stop4h 36m
Chicago Midway
Mon 8/24
1:25 pm-10:21 pm
2 stops8h 56m
$314
GulfportChicago
GPT - MDW
GPTMDW
Gulfport Biloxi Regional
Tue 9/1
4:00 pm-10:36 pm
1 stop6h 36m
Chicago Midway
Sat 9/5
4:39 pm-8:53 pm
1 stop4h 14m
$325
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Sat 10/24
5:14 pm-11:27 pm
1 stop6h 13m
Chicago O'Hare Intl
Wed 10/28
9:00 am-4:07 pm
1 stop7h 07m
$371
GulfportChicago
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Mon 11/23
6:00 pm-11:50 pm
1 stop5h 50m
Chicago O'Hare Intl
Wed 11/25
5:30 am-9:39 am
1 stop4h 09m
$376
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 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 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.
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
Hammond
Porter
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Other flights to Chicago
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Gulfport and Chicago flights
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Other flights from Gulfport
Browse through other flights departing from Gulfport. Flights are based on user searches made on Cheapflights and were last updated on June 24, 2026.
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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 June 24, 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 |