$180+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Sep 26 — Oct 31
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Gulfport with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Gulfport
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Cheapest flights from Chicago to GulfportExplore the most affordable flight options available from Chicago to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 27, 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 August 27, 2026.
This Delta deal was found by Cheapflights users on 8/22. 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 10/65:09 pm -
1 stop5h 07m
Tue 10/1310:03 am -
1 stop6h 11m
Deal found 8/22![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/22. 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 10/68:05 am -
1 stop4h 56m
Tue 10/131:46 pm -
1 stop6h 52m
Deal found 8/22![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/305:09 pm -
1 stop5h 07m
Tue 11/36:26 am -
1 stop4h 17m
Deal found 8/26![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:45 pm -
1 stop5h 47m
Tue 9/295:42 pm -
1 stop6h 17m
Deal found 8/24![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 8/23. 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 10/71:27 pm -
2 stops8h 49m
Wed 10/146:26 am -
2 stops6h 21m
Deal found 8/23![Delta logo]()
$311
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/291:27 pm -
2 stops8h 49m
Tue 11/34:00 pm -
1 stop6h 33m
Deal found 8/26![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/23. 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.
Sat 9/56:59 am -
2 stops8h 01m
Tue 9/155:59 pm -
1 stop6h 00m
Deal found 8/23![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/305:09 pm -
1 stop5h 07m
Mon 11/24:00 pm -
1 stop6h 33m
Deal found 8/26![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:20 am -
1 stop7h 52m
Thu 9/247:49 am -
1 stop8h 11m
Deal found 8/24![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/291:27 pm -
2 stops8h 49m
Mon 11/24:00 pm -
1 stop6h 33m
Deal found 8/26![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/291:56 pm -
2 stops8h 20m
Mon 11/24:00 pm -
1 stop4h 38m
Deal found 8/26![Delta logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/229:00 am -
1 stop10h 05m
Sun 10/257:45 pm -
1 stop11h 46m
Deal found 8/24![Multiple Airlines logo]()
$328
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 August 27, 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 August 27, 2026.
This Delta deal was found by Cheapflights users on 8/22. 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 10/65:09 pm -
1 stop5h 07m
Tue 10/1310:03 am -
1 stop6h 11m
Deal found 8/22![Delta logo]()
$301
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop7h 00m
Thu 10/85:14 pm -
1 stop7h 09m
Deal found 8/24![United Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 11/55:59 pm -
1 stop5h 32m
Fri 11/136:21 pm -
1 stop5h 38m
Deal found 8/25![American Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 8/22. 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 10/66:30 am -
1 stop6h 31m
Tue 10/1310:03 am -
1 stop6h 55m
Deal found 8/22![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/288:05 am -
1 stop4h 56m
Tue 11/36:26 am -
2 stops6h 33m
Deal found 8/26![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/2210:48 am -
1 stop6h 26m
Tue 9/295:59 pm -
1 stop4h 45m
Deal found 8/25![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/291:27 pm -
2 stops8h 49m
Tue 11/36:26 am -
2 stops6h 21m
Deal found 8/26![Delta logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/23. 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 10/312:22 pm -
1 stop5h 12m
Wed 11/44:55 pm -
2 stops16h 05m
Deal found 8/23![United Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Sun 9/65:30 am -
1 stop7h 54m
Sun 9/134:59 pm -
1 stop6h 28m
Deal found 8/22![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/104:19 pm -
1 stop4h 27m
Sat 10/174:00 pm -
1 stop6h 33m
Deal found 8/26![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/86:25 am -
1 stop7h 00m
Tue 10/135:14 pm -
1 stop6h 13m
Deal found 8/26![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 8/24. 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 9/297:05 am -
2 stops10h 09m
Sat 10/34:00 pm -
1 stop4h 56m
Deal found 8/24![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/107:00 am -
2 stops7h 21m
Sat 10/176:26 am -
2 stops10h 54m
Deal found 8/26![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 8/24. 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 9/299:29 am -
2 stops7h 45m
Sat 10/310:06 am -
2 stops8h 16m
Deal found 8/24![Delta logo]()
$450
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated August 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated August 27, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Thu 9/35:00 am -
1 stop5h 41m
Tue 9/155:35 am -
1 stop5h 34m
Deal found 8/23![American Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 8/23. 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.
Sat 9/56:59 am -
2 stops8h 01m
Tue 9/155:59 pm -
1 stop6h 00m
Deal found 8/23![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/84:53 pm -
1 stop5h 37m
Sat 9/1211:18 am -
1 stop7h 07m
Deal found 8/23![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Wed 9/96:30 am -
1 stop6h 54m
Sat 9/124:59 pm -
1 stop6h 27m
Deal found 8/26![United Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/105:30 am -
1 stop7h 54m
Mon 9/144:59 pm -
1 stop6h 28m
Deal found 8/26![United Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:20 am -
1 stop7h 52m
Thu 9/247:49 am -
1 stop8h 11m
Deal found 8/24![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/2210:48 am -
1 stop6h 26m
Tue 9/295:59 pm -
1 stop4h 45m
Deal found 8/25![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/245:00 am -
1 stop5h 40m
Sun 9/276:27 pm -
1 stop5h 32m
Deal found 8/26![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:45 pm -
1 stop5h 47m
Tue 9/295:42 pm -
1 stop6h 17m
Deal found 8/24![American Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:50 pm -
1 stop7h 34m
Sat 10/36:22 pm -
1 stop5h 52m
Deal found 8/24![American Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 8/24. 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 9/291:00 pm -
1 stop4h 14m
Sat 10/310:06 am -
1 stop5h 18m
Deal found 8/24![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 8/24. 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 9/297:05 am -
2 stops10h 09m
Sat 10/34:00 pm -
1 stop4h 56m
Deal found 8/24![Delta logo]()
$370
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 August 27, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated August 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sun 10/47:11 am -
2 stops25h 40m
Deal found 8/24![Multiple Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/2012:05 pm -
1 stop4h 59m
Deal found 8/25![American Airlines logo]()
$186
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/2011:19 am -
2 stops10h 57m
Deal found 8/25![Delta logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:16 am -
2 stops26h 35m
Deal found 8/25![Multiple Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/254:50 pm -
1 stop6h 34m
Deal found 8/26![American Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/194:30 pm -
1 stop4h 19m
Deal found 8/25![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/198:05 am -
1 stop6h 13m
Deal found 8/25![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 11/86:04 am -
1 stop6h 57m
Deal found 8/25![Delta logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Wed 9/97:28 pm -
3 stops37h 23m
Deal found 8/24![Multiple Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/222:00 pm -
2 stops8h 08m
Deal found 8/25![Delta logo]()
$214
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/2211:30 am -
2 stops10h 38m
Deal found 8/25![Delta logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/810:26 am -
2 stops22h 25m
Deal found 8/25![Multiple Airlines logo]()
$222
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 August 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Delta) |
One-way from | $180 (Kiwi.com) |
Popular in | April |
Cheapest in | February |
Average price | $296 |
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 7,457,451 searches. Data last updated August 27, 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 Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Tue 10/6
5:09 pm-10:16 pm
1 stop5h 07m
Gulfport Biloxi Regional
Tue 10/13
10:03 am-4:14 pm
1 stop6h 11m
$301
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 10/6
6:30 am-1:01 pm
1 stop6h 31m
Gulfport Biloxi Regional
Tue 10/13
10:03 am-4:58 pm
1 stop6h 55m
$301
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Wed 10/28
8:05 am-1:01 pm
1 stop4h 56m
Gulfport Biloxi Regional
Tue 11/3
6:26 am-12:59 pm
2 stops6h 33m
$306
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Tue 9/22
10:48 am-5:14 pm
1 stop6h 26m
Gulfport Biloxi Regional
Tue 9/29
5:59 pm-10:44 pm
1 stop4h 45m
$310
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Thu 10/29
1:27 pm-10:16 pm
2 stops8h 49m
Gulfport Biloxi Regional
Tue 11/3
6:26 am-12:47 pm
2 stops6h 21m
$320
Quickest round-trip
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Sat 10/10
4:19 pm-8:46 pm
1 stop4h 27m
Gulfport Biloxi Regional
Sat 10/17
4:00 pm-10:33 pm
1 stop6h 33m
$359
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 9/29
7:05 am-5:14 pm
2 stops10h 09m
Gulfport Biloxi Regional
Sat 10/3
4:00 pm-8:56 pm
1 stop4h 56m
$370
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sat 10/10
7:00 am-2:21 pm
2 stops7h 21m
Gulfport Biloxi Regional
Sat 10/17
6:26 am-5:20 pm
2 stops10h 54m
$399
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 10/6
6:25 am-1:25 pm
1 stop7h 00m
Gulfport Biloxi Regional
Thu 10/8
5:14 pm-12:23 am
1 stop7h 09m
$418
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Thu 11/5
5:59 pm-11:31 pm
1 stop5h 32m
Gulfport Biloxi Regional
Fri 11/13
6:21 pm-11:59 pm
1 stop5h 38m
$419
Showing 1-10 of 33 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 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 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, February is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $289). Flying from Chicago to Gulfport in January is currently the most expensive (average of $526). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How often are flights from Chicago to Gulfport delayed?
About 58% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 126 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 Thursday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Gulfport flights?
Over the last year, Sun Country Air have had the lowest number of delays on this route, with just 61% 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 August 27, 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.
Entertainment
7.8
Comfort
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Comfort
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Comfort
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Gulfport. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Gulfport?
Book flights to Gulfport if you plan to visit one of these locationsD'Iberville
Ocean Springs
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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 August 27, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on August 27, 2026.
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Top 2 airlines flying from Chicago to Gulfport
Discover the top 2 airlines that operate flights from Chicago to Gulfport. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$519 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$472 | FlexibilityNo cancel fee | On-timeN/A |