$142+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
May 19 — May 261
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 April 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 April 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:28 pm
ORD
- GPT
2 stops26h 12m
Multiple Airlines
Mon 5/115:31 pm
GPT
- ORD
1 stop18h 52m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:52 pm
ORD
- GPT
1 stop12h 08m
Multiple Airlines
Fri 5/16:54 pm
GPT
- ORD
1 stop23h 26m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 6/26:23 am
MDW
- GPT
1 stop6h 46m
Delta
Tue 6/96:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/17![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 6/27:07 am
ORD
- GPT
1 stop6h 02m
Delta
Tue 6/96:01 pm
GPT
- ORD
1 stop5h 58m
Delta
Deal found 4/17![Delta logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2512:58 pm
ORD
- GPT
1 stop18h 43m
Multiple Airlines
Mon 6/295:31 pm
GPT
- ORD
2 stops26h 22m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/78:30 am
ORD
- GPT
1 stop23h 11m
Multiple Airlines
Mon 5/115:31 pm
GPT
- ORD
1 stop18h 52m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:52 pm
ORD
- GPT
1 stop12h 08m
Multiple Airlines
Sun 5/37:20 pm
GPT
- ORD
2 stops36h 35m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 6/26:23 am
MDW
- GPT
1 stop6h 46m
Delta
Fri 6/126:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/17![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 4/14. 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.
Mon 5/116:41 pm
ORD
- GPT
1 stop5h 17m
American Airlines
Sat 5/166:09 pm
GPT
- ORD
1 stop5h 45m
American Airlines
Deal found 4/14![American Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Wed 6/35:11 pm
ORD
- GPT
1 stop25h 59m
Multiple Airlines
Sun 6/77:50 pm
GPT
- ORD
2 stops24h 42m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 6/25:15 pm
MDW
- GPT
1 stop4h 36m
Delta
Sat 6/133:00 pm
GPT
- MDW
1 stop7h 17m
Delta
Deal found 4/17![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 4/14. 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 5/45:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Sat 5/93:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/14![Delta logo]()
$334
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 April 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 April 19, 2026.
This Delta deal was found by Cheapflights users on 4/14. 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 5/45:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Sat 5/93:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/14![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Tue 6/910:30 am
ORD
- GPT
1 stop5h 41m
United Airlines
Sat 6/135:19 pm
GPT
- ORD
1 stop7h 26m
United Airlines
Deal found 4/16![United Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 4/18. 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.
Thu 6/116:40 am
ORD
- GPT
1 stop6h 27m
Delta
Mon 6/156:01 pm
GPT
- ORD
1 stop5h 58m
Delta
Deal found 4/18![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 4/16. 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.
Mon 5/116:23 am
MDW
- GPT
1 stop6h 46m
Delta
Sat 5/163:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/16![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 4/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 am
ORD
- GPT
1 stop7h 55m
United Airlines
Tue 6/22:00 pm
GPT
- ORD
1 stop7h 36m
United Airlines
Deal found 4/17![United Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 4/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:30 am
ORD
- GPT
1 stop6h 56m
United Airlines
Sat 10/105:15 pm
GPT
- ORD
1 stop6h 55m
United Airlines
Deal found 4/14![United Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:30 pm
ORD
- GPT
2 stops18h 51m
United Airlines
Mon 5/114:55 pm
GPT
- ORD
1 stop6h 20m
United Airlines
Deal found 4/15![United Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 4/18. 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.
Thu 6/1111:05 am
MDW
- GPT
1 stop6h 11m
Delta
Fri 6/126:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/18![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 4/18. 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.
Tue 6/306:40 am
ORD
- GPT
1 stop7h 04m
Delta
Thu 7/26:30 am
GPT
- ORD
1 stop6h 06m
Delta
Deal found 4/18![Delta logo]()
$517
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:05 am
ORD
- GPT
2 stops12h 48m
United Airlines
Sat 5/164:55 pm
GPT
- ORD
1 stop7h 50m
United Airlines
Deal found 4/15![United Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 4/18. 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 7/16:40 am
ORD
- GPT
1 stop7h 04m
Delta
Sun 7/51:53 pm
GPT
- ORD
1 stop6h 39m
Delta
Deal found 4/18![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 6/91:16 pm
MDW
- GPT
2 stops20h 05m
Delta
Thu 6/186:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/17![Delta logo]()
$521
This Delta deal was found by Cheapflights users on 4/16. 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.
Mon 9/75:25 pm
MDW
- GPT
1 stop4h 41m
Delta
Tue 9/156:00 am
GPT
- MDW
1 stop5h 54m
Delta
Deal found 4/16![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 4/16. 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 5/226:23 am
MDW
- GPT
1 stop6h 46m
Delta
Sun 5/2410:08 am
GPT
- MDW
1 stop5h 18m
Delta
Deal found 4/16![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 4/18. 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.
Sun 5/35:15 am
ORD
- GPT
1 stop4h 09m
Delta
Wed 5/65:55 pm
GPT
- ORD
1 stop6h 03m
Delta
Deal found 4/18![Delta logo]()
$601
This Delta deal was found by Cheapflights users on 4/18. 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.
Sat 6/67:00 am
ORD
- GPT
2 stops14h 51m
Delta
Wed 6/176:01 pm
GPT
- ORD
2 stops14h 04m
Delta
Deal found 4/18![Delta logo]()
$639
This Delta deal was found by Cheapflights users on 4/14. 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.
Thu 5/146:23 am
MDW
- GPT
1 stop6h 46m
Delta
Thu 5/2110:08 am
GPT
- MDW
1 stop6h 04m
Delta
Deal found 4/14![Delta logo]()
$678
This Delta deal was found by Cheapflights users on 4/15. 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.
Fri 5/226:23 am
MDW
- GPT
1 stop6h 46m
Delta
Mon 5/256:32 am
GPT
- MDW
1 stop5h 24m
Delta
Deal found 4/15![Delta logo]()
$678
This Delta deal was found by Cheapflights users on 4/15. 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.
Thu 6/256:05 am
MDW
- GPT
1 stop7h 02m
Delta
Mon 6/2910:06 am
GPT
- MDW
1 stop6h 40m
Delta
Deal found 4/15![Delta logo]()
$729
This Delta deal was found by Cheapflights users on 4/17. 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.
Mon 6/110:59 am
MDW
- GPT
1 stop6h 15m
Delta
Tue 6/96:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/17![Delta logo]()
$879
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated April 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:52 pm
ORD
- GPT
1 stop12h 08m
Multiple Airlines
Fri 5/16:54 pm
GPT
- ORD
1 stop23h 26m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:52 pm
ORD
- GPT
1 stop12h 08m
Multiple Airlines
Sun 5/37:20 pm
GPT
- ORD
2 stops36h 35m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:52 pm
ORD
- GPT
1 stop12h 08m
Multiple Airlines
Thu 4/307:20 pm
GPT
- ORD
1 stop13h 45m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:26 am
MDW
- GPT
1 stop10h 14m
Multiple Airlines
Thu 4/307:20 pm
GPT
- MDW
2 stops24h 11m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 4/15. 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 4/2911:15 am
ORD
- GPT
1 stop6h 18m
American Airlines
Sat 5/26:09 pm
GPT
- ORD
1 stop5h 45m
American Airlines
Deal found 4/15![American Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:28 pm
ORD
- GPT
2 stops26h 12m
Multiple Airlines
Mon 5/115:31 pm
GPT
- ORD
1 stop18h 52m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 4/17. 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.
Sat 5/25:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Wed 5/65:55 pm
GPT
- MDW
1 stop4h 33m
Delta
Deal found 4/17![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 4/14. 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 5/45:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Sat 5/93:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/14![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/78:30 am
ORD
- GPT
1 stop23h 11m
Multiple Airlines
Mon 5/115:31 pm
GPT
- ORD
1 stop18h 52m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 4/14. 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.
Mon 5/116:41 pm
ORD
- GPT
1 stop5h 17m
American Airlines
Sat 5/166:09 pm
GPT
- ORD
1 stop5h 45m
American Airlines
Deal found 4/14![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 4/14. 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 5/116:23 am
MDW
- GPT
1 stop6h 46m
Delta
Sat 5/163:00 pm
GPT
- MDW
1 stop6h 09m
Delta
Deal found 4/14![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 4/17. 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.
Sun 5/316:23 am
MDW
- GPT
1 stop6h 46m
Delta
Tue 6/96:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/17![Delta logo]()
$404
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 April 19, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 5/29:16 am
ORD
- GPT
2 stops33h 24m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Sun 6/75:25 am
ORD
- GPT
2 stops26h 16m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Sat 6/136:55 am
ORD
- GPT
2 stops36h 15m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 5/158:59 pm
ORD
- GPT
3 stops46h 11m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 6/105:25 pm
ORD
- GPT
1 stop25h 45m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Thu 6/116:55 am
ORD
- GPT
2 stops12h 15m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 4/18. 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.
Tue 6/98:03 am
ORD
- GPT
1 stop5h 04m
Delta
Deal found 4/18![Delta logo]()
$240
This Delta deal was found by Cheapflights users on 4/15. 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.
Fri 5/156:23 am
MDW
- GPT
1 stop6h 46m
Delta
Deal found 4/15![Delta logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:20 pm
MDW
- GPT
3 stops43h 13m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$717
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 April 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $278 (Kiwi.com) |
One-way from | $142 (Kiwi.com) |
Popular in | November |
Cheapest in | August |
Average price | $378 |
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 April 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
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Mon 5/4
5:21 pm-10:13 pm
1 stop4h 52m
Gulfport Biloxi Regional
Sat 5/9
3:00 pm-9:09 pm
1 stop6h 09m
$334
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 6/11
6:40 am-1:07 pm
1 stop6h 27m
Gulfport Biloxi Regional
Mon 6/15
6:01 pm-11:59 pm
1 stop5h 58m
$399
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Mon 5/11
6:23 am-1:09 pm
1 stop6h 46m
Gulfport Biloxi Regional
Sat 5/16
3:00 pm-9:09 pm
1 stop6h 09m
$419
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 6/9
10:30 am-4:11 pm
1 stop5h 41m
Gulfport Biloxi Regional
Sat 6/13
5:19 pm-12:45 am
1 stop7h 26m
$463
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sat 5/30
5:30 am-1:25 pm
1 stop7h 55m
Gulfport Biloxi Regional
Tue 6/2
2:00 pm-9:36 pm
1 stop7h 36m
$463
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 10/6
6:30 am-1:26 pm
1 stop6h 56m
Gulfport Biloxi Regional
Sat 10/10
5:15 pm-12:10 am
1 stop6h 55m
$464
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 5/8
6:30 pm-1:21 pm
2 stops18h 51m
Gulfport Biloxi Regional
Mon 5/11
4:55 pm-11:15 pm
1 stop6h 20m
$506
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Thu 6/11
11:05 am-5:16 pm
1 stop6h 11m
Gulfport Biloxi Regional
Fri 6/12
6:01 pm-10:17 pm
1 stop4h 16m
$508
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 6/30
6:40 am-1:44 pm
1 stop7h 04m
Gulfport Biloxi Regional
Thu 7/2
6:30 am-12:36 pm
1 stop6h 06m
$517
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Wed 7/1
6:40 am-1:44 pm
1 stop7h 04m
Gulfport Biloxi Regional
Sun 7/5
1:53 pm-8:32 pm
1 stop6h 39m
$519
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 April.
| 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, January is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $248). Flying from Chicago to Gulfport in March is currently the most expensive (average of $373). 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 much does it cost to fly round-trip from Chicago to Gulfport?
How often are flights from Chicago to Gulfport delayed?
About 53% 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 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 April 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.
Crew
8.5
Entertainment
7.8
Overall
7.9
Comfort
7.9
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Entertainment
7.8
Overall
7.9
Comfort
7.9
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Entertainment
7.8
Overall
7.9
Comfort
7.9
Food
7.2
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - 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 locationsOcean Springs
D'Iberville
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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 April 19, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on April 19, 2026.
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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 April 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$323 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$419 | FlexibilityNo cancel fee | On-timeN/A |