$206+ Cheap flights from Chicago (CHI) to Gulfport (GPT)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Nov 26 — Dec 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 October 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 October 27, 2026.
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/46:50 am -
1 stop5h 27m
Tue 12/85:42 pm -
1 stop6h 17m
Deal found 10/22![American Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:51 am -
1 stop9h 14m
Mon 11/166:46 pm -
2 stops29h 35m
Deal found 10/23![Multiple Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 10/22. 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 12/411:28 am -
1 stop5h 56m
Tue 12/86:15 am -
1 stop4h 13m
Deal found 10/22![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 10/26. 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 12/46:00 am -
1 stop7h 09m
Mon 12/76:09 pm -
1 stop4h 45m
Deal found 10/26![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/46:45 pm -
1 stop5h 10m
Mon 12/76:23 pm -
1 stop5h 36m
Deal found 10/26![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/76:55 am -
1 stop6h 23m
Wed 11/114:55 pm -
1 stop6h 31m
Deal found 10/23![United Airlines logo]()
$343
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/125:00 am -
1 stop6h 11m
Mon 11/166:21 pm -
1 stop5h 38m
Deal found 10/23![American Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:31 am -
2 stops25h 20m
Sun 11/227:45 pm -
1 stop28h 58m
Deal found 10/23![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:21 am -
1 stop11h 45m
Mon 12/76:46 pm -
2 stops19h 44m
Deal found 10/26![Multiple Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/101:05 pm -
1 stop4h 14m
Sat 11/1410:04 am -
1 stop5h 08m
Deal found 10/26![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 11/108:05 am -
1 stop5h 13m
Sat 11/146:45 am -
1 stop7h 38m
Deal found 10/26![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/1010:06 am -
2 stops11h 46m
Sat 11/1410:04 am -
1 stop4h 48m
Deal found 10/26![Delta logo]()
$374
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 October 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 October 27, 2026.
This Delta deal was found by Cheapflights users on 10/26. 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 1/233:00 pm -
1 stop7h 08m
Tue 1/264:00 pm -
1 stop6h 20m
Deal found 10/26![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/76:55 am -
1 stop6h 23m
Wed 11/114:55 pm -
1 stop6h 31m
Deal found 10/23![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 10/22. 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 12/411:28 am -
1 stop5h 56m
Tue 12/86:15 am -
1 stop4h 13m
Deal found 10/22![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 10/26. 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 12/46:00 am -
1 stop7h 09m
Mon 12/76:09 pm -
1 stop4h 45m
Deal found 10/26![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/23. 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.
Thu 11/196:55 am -
1 stop6h 23m
Sun 11/224:55 pm -
1 stop7h 50m
Deal found 10/23![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/1010:06 am -
2 stops11h 46m
Sat 11/1410:04 am -
1 stop4h 48m
Deal found 10/26![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/23. 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 11/74:19 pm -
1 stop4h 27m
Wed 11/116:04 pm -
1 stop4h 50m
Deal found 10/23![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 10/23. 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 11/78:29 am -
2 stops12h 17m
Wed 11/116:26 am -
2 stops10h 22m
Deal found 10/23![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Thu 11/512:40 pm -
1 stop6h 54m
Fri 11/134:55 pm -
1 stop7h 50m
Deal found 10/24![United Airlines logo]()
$549
This Delta deal was found by Cheapflights users on 10/23. 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 1/812:15 pm -
2 stops9h 52m
Tue 1/126:00 am -
2 stops6h 37m
Deal found 10/23![Delta logo]()
$408
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Fri 10/307:29 am -
1 stop5h 49m
Mon 11/24:55 pm -
1 stop7h 50m
Deal found 10/22![United Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 10/23. 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 12/259:59 am -
2 stops9h 34m
Fri 1/14:40 pm -
1 stop6h 23m
Deal found 10/23![Delta logo]()
$414
This United Airlines deal was found by Cheapflights users on 10/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:55 am -
1 stop6h 23m
Fri 11/131:54 pm -
2 stops17h 05m
Deal found 10/25![United Airlines logo]()
$624
This Delta deal was found by Cheapflights users on 10/23. 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 1/812:30 pm -
2 stops9h 37m
Tue 1/1210:30 am -
2 stops8h 07m
Deal found 10/23![Delta logo]()
$462
This Delta deal was found by Cheapflights users on 10/22. 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 12/319:00 am -
1 stop6h 43m
Sun 1/35:20 pm -
1 stop6h 39m
Deal found 10/22![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 10/23. 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 12/259:58 am -
1 stop5h 45m
Fri 1/14:40 pm -
1 stop5h 42m
Deal found 10/23![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 10/25. 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.
Wed 11/115:13 pm -
1 stop4h 39m
Fri 11/136:04 pm -
1 stop4h 50m
Deal found 10/25![Delta logo]()
$632
This Delta deal was found by Cheapflights users on 10/25. 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 11/101:05 pm -
1 stop4h 14m
Thu 11/1210:04 am -
1 stop6h 14m
Deal found 10/25![Delta logo]()
$632
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated October 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated October 27, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/76:55 am -
1 stop6h 23m
Wed 11/114:55 pm -
1 stop6h 31m
Deal found 10/23![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 10/23. 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 11/74:19 pm -
1 stop4h 27m
Wed 11/116:04 pm -
1 stop4h 50m
Deal found 10/23![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 10/23. 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 11/710:30 am -
2 stops10h 16m
Wed 11/116:26 am -
1 stop5h 54m
Deal found 10/23![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/101:05 pm -
1 stop4h 14m
Sat 11/1410:04 am -
1 stop5h 08m
Deal found 10/26![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 11/108:05 am -
1 stop5h 13m
Sat 11/146:45 am -
1 stop7h 38m
Deal found 10/26![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/1010:06 am -
2 stops11h 46m
Sat 11/1410:04 am -
1 stop4h 48m
Deal found 10/26![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/25. 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.
Wed 11/111:31 pm -
2 stops8h 21m
Sat 11/146:26 am -
2 stops10h 13m
Deal found 10/25![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/25. 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.
Wed 11/1110:06 am -
2 stops11h 46m
Sat 11/146:26 am -
2 stops10h 15m
Deal found 10/25![Delta logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:51 am -
1 stop9h 14m
Mon 11/166:46 pm -
2 stops29h 35m
Deal found 10/23![Multiple Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/125:00 am -
1 stop6h 11m
Mon 11/166:21 pm -
1 stop5h 38m
Deal found 10/23![American Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:31 am -
2 stops25h 20m
Sun 11/227:45 pm -
1 stop28h 58m
Deal found 10/23![Multiple Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Sun 11/226:49 pm -
1 stop5h 12m
Thu 11/265:16 am -
1 stop7h 07m
Deal found 10/26![American Airlines logo]()
$339
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 October 27, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
This Delta deal was found by Cheapflights users on 10/24. 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 1/59:50 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$206
This American Airlines deal was found by Cheapflights users on 10/24. 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 11/205:00 am -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![American Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 11/2010:00 pm -
2 stops45h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Fri 11/208:16 am -
3 stops58h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 10/24. 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.
Fri 11/2012:30 pm -
2 stops9h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$415
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 October 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Delta) |
One-way from | $206 (Delta) |
Popular in | April |
Cheapest in | February |
Average price | $424 |
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 October 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
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 1/5
6:00 am-3:49 pm
2 stops9h 49m
Gulfport Biloxi Regional
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$211
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sat 1/23
3:00 pm-10:08 pm
1 stop7h 08m
Gulfport Biloxi Regional
Tue 1/26
4:00 pm-10:20 pm
1 stop6h 20m
$321
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Fri 12/4
11:28 am-5:24 pm
1 stop5h 56m
Gulfport Biloxi Regional
Tue 12/8
6:15 am-10:28 am
1 stop4h 13m
$338
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Fri 12/4
6:00 am-1:09 pm
1 stop7h 09m
Gulfport Biloxi Regional
Mon 12/7
6:09 pm-10:54 pm
1 stop4h 45m
$339
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sat 11/7
6:55 am-1:18 pm
1 stop6h 23m
Gulfport Biloxi Regional
Wed 11/11
4:55 pm-11:26 pm
1 stop6h 31m
$343
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Tue 11/10
10:06 am-9:52 pm
2 stops11h 46m
Gulfport Biloxi Regional
Sat 11/14
10:04 am-2:52 pm
1 stop4h 48m
$374
Quickest round-trip
ChicagoGulfport
MDW Chicago Midway - GPT Gulfport Biloxi Regional
MDWGPT
Chicago Midway
Sat 11/7
4:19 pm-8:46 pm
1 stop4h 27m
Gulfport Biloxi Regional
Wed 11/11
6:04 pm-10:54 pm
1 stop4h 50m
$389
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Sat 11/7
8:29 am-8:46 pm
2 stops12h 17m
Gulfport Biloxi Regional
Wed 11/11
6:26 am-4:48 pm
2 stops10h 22m
$399
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Thu 11/19
6:55 am-1:18 pm
1 stop6h 23m
Gulfport Biloxi Regional
Sun 11/22
4:55 pm-12:45 am
1 stop7h 50m
$402
ChicagoGulfport
ORD Chicago O'Hare Intl - GPT Gulfport Biloxi Regional
ORDGPT
Chicago O'Hare Intl
Fri 1/8
12:15 pm-10:07 pm
2 stops9h 52m
Gulfport Biloxi Regional
Tue 1/12
6:00 am-12:37 pm
2 stops6h 37m
$408
Showing 1-10 of 21 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 $550). 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 59% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 143 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 Saturday 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 59% 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 October 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.
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - 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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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 October 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$268 | Average$620 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$293 | Average$519 | FlexibilityNo cancel fee | On-time71% |