$154+ Cheap flights from Chicago (CHI) to Gulfport (GPT)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Aug 18 — Aug 251
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 July 19, 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 July 19, 2026.
This American Airlines deal was found by Cheapflights users on 7/15. 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 8/293:54 pm
ORD
- GPT
1 stop7h 22m
American Airlines
Sat 9/55:31 am
GPT
- ORD
1 stop7h 57m
American Airlines
Deal found 7/15![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 7/15. 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 8/157:30 am
ORD
- GPT
1 stop5h 47m
American Airlines
Sat 8/226:34 pm
GPT
- ORD
1 stop5h 44m
American Airlines
Deal found 7/15![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 7/15. 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 8/125:10 pm
MDW
- GPT
1 stop5h 11m
Delta
Wed 8/196:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Deal found 7/15![Delta logo]()
$300
This American Airlines deal was found by Cheapflights users on 7/15. 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 8/126:49 am
ORD
- GPT
1 stop6h 28m
American Airlines
Wed 8/191:50 pm
GPT
- ORD
1 stop5h 56m
American Airlines
Deal found 7/15![American Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/125:13 pm
ORD
- GPT
1 stop25h 32m
Multiple Airlines
Mon 8/175:31 pm
GPT
- ORD
2 stops19h 19m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/125:13 pm
ORD
- GPT
1 stop25h 32m
Multiple Airlines
Sun 8/167:25 pm
GPT
- ORD
1 stop13h 46m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 7/15. 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 8/123:25 pm
ORD
- GPT
1 stop6h 56m
Delta
Wed 8/196:30 am
GPT
- ORD
2 stops9h 47m
Delta
Deal found 7/15![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 7/15. 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 8/56:05 am
MDW
- GPT
1 stop6h 58m
Delta
Sat 8/84:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Deal found 7/15![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/65:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Sun 8/95:50 pm
GPT
- ORD
1 stop6h 06m
American Airlines
Deal found 7/14![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 7/15. 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 8/51:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Sat 8/84:00 pm
GPT
- ORD
1 stop4h 55m
Delta
Deal found 7/15![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/55:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Sat 8/85:45 pm
GPT
- ORD
1 stop6h 07m
American Airlines
Deal found 7/16![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/115:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Thu 8/136:34 pm
GPT
- ORD
1 stop5h 44m
American Airlines
Deal found 7/16![American Airlines logo]()
$327
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 July 19, 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 July 19, 2026.
This Delta deal was found by Cheapflights users on 7/15. 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 8/125:10 pm
MDW
- GPT
1 stop5h 11m
Delta
Wed 8/196:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Deal found 7/15![Delta logo]()
$300
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/65:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Sun 8/95:50 pm
GPT
- ORD
1 stop6h 06m
American Airlines
Deal found 7/14![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 7/16. 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 7/316:29 am
ORD
- GPT
1 stop6h 56m
United Airlines
Tue 8/42:00 pm
GPT
- ORD
1 stop7h 40m
United Airlines
Deal found 7/16![United Airlines logo]()
$561
This American Airlines deal was found by Cheapflights users on 7/18. 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 8/216:49 am
ORD
- GPT
1 stop6h 28m
American Airlines
Sun 8/235:31 am
GPT
- ORD
1 stop5h 40m
American Airlines
Deal found 7/18![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 7/18. 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 8/56:05 am
MDW
- GPT
1 stop6h 58m
Delta
Sat 8/84:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Deal found 7/18![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 7/17. 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 8/51:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Sat 8/810:01 am
GPT
- ORD
2 stops10h 29m
Delta
Deal found 7/17![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 7/18. 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 8/2111:22 am
ORD
- GPT
2 stops10h 59m
Delta
Sun 8/236:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 7/18![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 7/15. 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 9/113:50 pm
ORD
- GPT
1 stop7h 34m
American Airlines
Sun 9/136:27 pm
GPT
- ORD
1 stop5h 32m
American Airlines
Deal found 7/15![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 7/16. 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 7/3112:41 pm
MDW
- GPT
1 stop4h 31m
Delta
Tue 8/410:01 am
GPT
- MDW
2 stops8h 32m
Delta
Deal found 7/16![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:54 am
ORD
- GPT
1 stop5h 06m
Delta
Mon 9/76:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 7/14![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 7/15. 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 8/46:05 am
MDW
- GPT
1 stop6h 58m
Delta
Thu 8/610:01 am
GPT
- MDW
1 stop6h 14m
Delta
Deal found 7/15![Delta logo]()
$425
This Delta deal was found by Cheapflights users on 7/14. 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 8/101:25 pm
MDW
- GPT
2 stops8h 56m
Delta
Mon 8/176:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Deal found 7/14![Delta logo]()
$428
This Delta deal was found by Cheapflights users on 7/16. 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 8/61:25 pm
MDW
- GPT
2 stops8h 56m
Delta
Mon 8/106:30 am
GPT
- MDW
1 stop5h 21m
Delta
Deal found 7/16![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:24 am
MDW
- GPT
2 stops11h 29m
Delta
Sat 9/54:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Deal found 7/15![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 7/16. 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 8/41:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Thu 8/66:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 7/16![Delta logo]()
$476
This Delta deal was found by Cheapflights users on 7/16. 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 8/67:05 am
ORD
- GPT
2 stops10h 10m
Delta
Mon 8/106:00 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 7/16![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 7/14. 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 8/71:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Mon 8/101:48 pm
GPT
- ORD
1 stop7h 07m
Delta
Deal found 7/14![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 7/14. 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 8/281:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Fri 9/44:00 pm
GPT
- ORD
1 stop4h 55m
Delta
Deal found 7/14![Delta logo]()
$557
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated July 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated July 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/15. 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 8/56:05 am
MDW
- GPT
1 stop6h 58m
Delta
Sat 8/84:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Deal found 7/15![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 7/15. 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 8/51:59 pm
ORD
- GPT
2 stops8h 22m
Delta
Sat 8/84:00 pm
GPT
- ORD
1 stop4h 55m
Delta
Deal found 7/15![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/55:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Sat 8/85:45 pm
GPT
- ORD
1 stop6h 07m
American Airlines
Deal found 7/16![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 7/14. 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 8/65:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Sun 8/95:50 pm
GPT
- ORD
1 stop6h 06m
American Airlines
Deal found 7/14![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/115:00 am
ORD
- GPT
1 stop5h 41m
American Airlines
Thu 8/136:34 pm
GPT
- ORD
1 stop5h 44m
American Airlines
Deal found 7/16![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/15. 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 8/125:10 pm
MDW
- GPT
1 stop5h 11m
Delta
Wed 8/196:00 pm
GPT
- MDW
1 stop4h 36m
Delta
Deal found 7/15![Delta logo]()
$300
This American Airlines deal was found by Cheapflights users on 7/15. 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 8/126:49 am
ORD
- GPT
1 stop6h 28m
American Airlines
Wed 8/191:50 pm
GPT
- ORD
1 stop5h 56m
American Airlines
Deal found 7/15![American Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/125:13 pm
ORD
- GPT
1 stop25h 32m
Multiple Airlines
Mon 8/175:31 pm
GPT
- ORD
2 stops19h 19m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/125:13 pm
ORD
- GPT
1 stop25h 32m
Multiple Airlines
Sun 8/167:25 pm
GPT
- ORD
1 stop13h 46m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 7/15. 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 8/123:25 pm
ORD
- GPT
1 stop6h 56m
Delta
Wed 8/196:30 am
GPT
- ORD
2 stops9h 47m
Delta
Deal found 7/15![Delta logo]()
$305
This American Airlines deal was found by Cheapflights users on 7/15. 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 8/157:30 am
ORD
- GPT
1 stop5h 47m
American Airlines
Sat 8/226:34 pm
GPT
- ORD
1 stop5h 44m
American Airlines
Deal found 7/15![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 7/15. 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 8/293:54 pm
ORD
- GPT
1 stop7h 22m
American Airlines
Sat 9/55:31 am
GPT
- ORD
1 stop7h 57m
American Airlines
Deal found 7/15![American Airlines logo]()
$289
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 July 19, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated July 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/271:03 pm
ORD
- GPT
3 stops18h 38m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 7/16. 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 8/66:05 am
MDW
- GPT
1 stop6h 58m
Delta
Deal found 7/16![Delta logo]()
$164
This United Airlines deal was found by Cheapflights users on 7/16. 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 8/66:29 am
ORD
- GPT
1 stop6h 56m
United Airlines
Deal found 7/16![United Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 10/47:45 am
ORD
- GPT
2 stops25h 06m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 7/17. 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 8/276:05 am
MDW
- GPT
1 stop6h 58m
Delta
Deal found 7/17![Delta logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 8/61:50 pm
ORD
- GPT
2 stops17h 51m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/2711:50 am
MDW
- GPT
2 stops19h 51m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 10/412:03 pm
MDW
- GPT
3 stops20h 48m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 8/66:05 am
MDW
- GPT
2 stops12h 40m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 7/16. 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 10/46:05 am
MDW
- GPT
1 stop7h 06m
Delta
Deal found 7/16![Delta logo]()
$250
This American Airlines deal was found by Cheapflights users on 7/16. 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 10/45:18 am
ORD
- GPT
1 stop6h 47m
American Airlines
Deal found 7/16![American Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 7/18. 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 7/226:00 am
MDW
- GPT
1 stop7h 05m
Delta
Deal found 7/18![Delta logo]()
$262
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 July 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (American Airlines) |
One-way from | $154 (Kiwi.com) |
Popular in | April |
Cheapest in | February |
Average price | $290 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Gulfport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 19, 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
Quickest round-trip
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Wed 8/12
5:10 pm-10:21 pm
1 stop5h 11m
Gulfport Biloxi Regional
Wed 8/19
6:00 pm-10:36 pm
1 stop4h 36m
$300
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 8/6
5:00 am-10:41 am
1 stop5h 41m
Gulfport Biloxi Regional
Sun 8/9
5:50 pm-11:56 pm
1 stop6h 06m
$309
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 8/21
6:49 am-1:17 pm
1 stop6h 28m
Gulfport Biloxi Regional
Sun 8/23
5:31 am-11:11 am
1 stop5h 40m
$309
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Wed 8/5
6:05 am-1:03 pm
1 stop6h 58m
Gulfport Biloxi Regional
Sat 8/8
4:00 pm-10:36 pm
1 stop6h 36m
$324
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Wed 8/5
1:59 pm-10:21 pm
2 stops8h 22m
Gulfport Biloxi Regional
Sat 8/8
10:01 am-8:30 pm
2 stops10h 29m
$335
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 8/21
11:22 am-10:21 pm
2 stops10h 59m
Gulfport Biloxi Regional
Sun 8/23
6:00 pm-11:57 pm
1 stop5h 57m
$359
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 9/11
3:50 pm-11:24 pm
1 stop7h 34m
Gulfport Biloxi Regional
Sun 9/13
6:27 pm-11:59 pm
1 stop5h 32m
$404
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 7/31
12:41 pm-5:12 pm
1 stop4h 31m
Gulfport Biloxi Regional
Tue 8/4
10:01 am-6:33 pm
2 stops8h 32m
$414
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 9/4
9:54 am-3:00 pm
1 stop5h 06m
Gulfport Biloxi Regional
Mon 9/7
6:00 pm-11:57 pm
1 stop5h 57m
$423
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Tue 8/4
6:05 am-1:03 pm
1 stop6h 58m
Gulfport Biloxi Regional
Thu 8/6
10:01 am-4:15 pm
1 stop6h 14m
$425
Showing 1-10 of 35 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 July.
| 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 56% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 121 minutes.
What is the most punctual flight time for Chicago to Gulfport flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Gulfport flights?
Over the last year, Sun Country Air have had the lowest number of delays on this route, with just 64% 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 July 19, 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
Overall
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from 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 July 19, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on July 19, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Gulfport
Discover the top 2 airlines that operate flights from Chicago to Gulfport. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 19, 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 |