$209+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Jun 18 — Jun 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 May 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 May 19, 2026.
This Delta deal was found by Cheapflights users on 5/16. 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.
Wed 8/265:10 pm
MDW
- GPT
1 stop5h 11m
Delta
Sat 8/294:00 pm
GPT
- MDW
1 stop6h 36m
Delta
Deal found 5/16![Delta logo]()
$291
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 7/85:00 am
ORD
- GPT
1 stop5h 55m
American Airlines
Sat 7/116:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 5/14![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 5/16. 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.
Wed 8/2612:29 pm
ORD
- GPT
2 stops9h 52m
Delta
Sat 8/294:00 pm
GPT
- ORD
1 stop4h 46m
Delta
Deal found 5/16![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 5/14. 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 7/31:46 pm
ORD
- GPT
1 stop6h 55m
Delta
Mon 7/131:50 pm
GPT
- ORD
1 stop6h 43m
Delta
Deal found 5/14![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 5/15. 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 9/307:10 am
ORD
- GPT
1 stop6h 23m
Delta
Sun 10/410:30 am
GPT
- ORD
2 stops8h 11m
Delta
Deal found 5/15![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 5/15. 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.
Mon 7/136:35 am
ORD
- GPT
1 stop6h 30m
Delta
Mon 7/206:30 am
GPT
- ORD
1 stop6h 04m
Delta
Deal found 5/15![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Fri 5/296:47 pm
ORD
- GPT
1 stop5h 14m
American Airlines
Wed 6/36:38 pm
GPT
- ORD
1 stop5h 21m
American Airlines
Deal found 5/14![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 5/16. 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 7/156:47 pm
ORD
- GPT
1 stop5h 09m
American Airlines
Sat 7/186:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 5/16![American Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 5/14. 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 10/25:55 pm
ORD
- GPT
1 stop4h 11m
Delta
Tue 10/66:00 am
GPT
- ORD
1 stop6h 06m
Delta
Deal found 5/14![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 5/18. 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 6/106:35 am
ORD
- GPT
1 stop6h 32m
Delta
Sat 6/133:00 pm
GPT
- ORD
1 stop5h 59m
Delta
Deal found 5/18![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/16. 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 7/136:00 am
MDW
- GPT
1 stop7h 05m
Delta
Mon 7/206:30 am
GPT
- MDW
1 stop5h 26m
Delta
Deal found 5/16![Delta logo]()
$334
This American Airlines deal was found by Cheapflights users on 5/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:00 am
ORD
- GPT
1 stop5h 55m
American Airlines
Mon 7/136:35 pm
GPT
- ORD
1 stop5h 26m
American Airlines
Deal found 5/17![American Airlines 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 May 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 May 19, 2026.
This Delta deal was found by Cheapflights users on 5/14. 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 7/33:22 pm
ORD
- GPT
1 stop5h 19m
Delta
Mon 7/136:30 am
GPT
- ORD
2 stops8h 35m
Delta
Deal found 5/14![Delta logo]()
$330
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Thu 5/215:30 am
ORD
- GPT
1 stop7h 55m
United Airlines
Sat 5/235:24 pm
GPT
- ORD
1 stop5h 51m
United Airlines
Deal found 5/17![United Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 5/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:10 am
ORD
- GPT
1 stop5h 04m
American Airlines
Thu 7/26:32 pm
GPT
- ORD
1 stop5h 29m
American Airlines
Deal found 5/17![American Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 5/16. 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 10/25:25 pm
MDW
- GPT
1 stop4h 41m
Delta
Tue 10/610:30 am
GPT
- MDW
1 stop5h 55m
Delta
Deal found 5/16![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 5/14. 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 7/34:25 pm
MDW
- GPT
1 stop4h 16m
Delta
Mon 7/136:30 am
GPT
- MDW
1 stop5h 26m
Delta
Deal found 5/14![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 5/14. 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 7/136:00 am
MDW
- GPT
1 stop7h 05m
Delta
Mon 7/206:30 am
GPT
- MDW
1 stop5h 26m
Delta
Deal found 5/14![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 5/13. 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 6/116:35 am
ORD
- GPT
1 stop6h 32m
Delta
Mon 6/151:53 pm
GPT
- ORD
1 stop6h 39m
Delta
Deal found 5/13![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 5/17. 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.
Fri 7/1712:41 pm
MDW
- GPT
1 stop4h 34m
Delta
Tue 7/216:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 5/17![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 5/17. 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 9/171:05 pm
MDW
- GPT
1 stop4h 12m
Delta
Sun 9/206:00 am
GPT
- MDW
2 stops6h 30m
Delta
Deal found 5/17![Delta logo]()
$423
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Tue 6/308:51 am
ORD
- GPT
1 stop7h 20m
United Airlines
Thu 7/25:19 pm
GPT
- ORD
2 stops21h 31m
United Airlines
Deal found 5/17![United Airlines logo]()
$712
This Delta deal was found by Cheapflights users on 5/15. 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 6/25:15 pm
MDW
- GPT
1 stop4h 36m
Delta
Sun 6/145:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 5/15![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 5/16. 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 7/166:00 am
MDW
- GPT
1 stop7h 05m
Delta
Tue 7/216:00 pm
GPT
- MDW
2 stops15h 08m
Delta
Deal found 5/16![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 5/17. 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 7/1312:27 pm
ORD
- GPT
2 stops9h 47m
Delta
Mon 7/201:50 pm
GPT
- ORD
1 stop4h 55m
Delta
Deal found 5/17![Delta logo]()
$552
This Delta deal was found by Cheapflights users on 5/16. 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 7/166:00 am
MDW
- GPT
1 stop7h 05m
Delta
Sun 7/196:30 am
GPT
- MDW
1 stop5h 26m
Delta
Deal found 5/16![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 5/16. 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.
Sat 7/189:00 am
ORD
- GPT
1 stop5h 50m
Delta
Mon 7/206:00 pm
GPT
- ORD
2 stops13h 59m
Delta
Deal found 5/16![Delta logo]()
$631
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated May 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated May 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Fri 5/296:47 pm
ORD
- GPT
1 stop5h 14m
American Airlines
Wed 6/36:38 pm
GPT
- ORD
1 stop5h 21m
American Airlines
Deal found 5/14![American Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 5/14. 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 5/298:42 am
ORD
- GPT
2 stops8h 32m
Delta
Wed 6/36:02 pm
GPT
- ORD
1 stop6h 06m
Delta
Deal found 5/14![Delta logo]()
$363
This American Airlines deal was found by Cheapflights users on 5/18. 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 5/296:47 pm
ORD
- GPT
1 stop5h 14m
American Airlines
Mon 6/16:38 pm
GPT
- ORD
1 stop5h 27m
American Airlines
Deal found 5/18![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 5/18. 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 5/303:00 pm
ORD
- GPT
1 stop6h 51m
Delta
Tue 6/21:55 pm
GPT
- ORD
1 stop4h 46m
Delta
Deal found 5/18![Delta logo]()
$385
This Delta deal was found by Cheapflights users on 5/18. 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 6/37:05 am
ORD
- GPT
2 stops10h 09m
Delta
Sat 6/63:00 pm
GPT
- ORD
1 stop5h 36m
Delta
Deal found 5/18![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/18. 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 6/612:30 pm
ORD
- GPT
2 stops9h 21m
Delta
Tue 6/95:56 pm
GPT
- ORD
1 stop6h 03m
Delta
Deal found 5/18![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 5/18. 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 6/106:35 am
ORD
- GPT
1 stop6h 32m
Delta
Sat 6/133:00 pm
GPT
- ORD
1 stop5h 59m
Delta
Deal found 5/18![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/13. 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 6/116:35 am
ORD
- GPT
1 stop6h 32m
Delta
Mon 6/151:53 pm
GPT
- ORD
1 stop6h 39m
Delta
Deal found 5/13![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 5/18. 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 6/126:35 am
ORD
- GPT
1 stop6h 32m
Delta
Mon 6/155:56 pm
GPT
- ORD
1 stop6h 03m
Delta
Deal found 5/18![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 5/18. 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.
Sat 6/205:00 am
ORD
- GPT
1 stop5h 50m
American Airlines
Tue 6/236:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/18![American Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 5/15. 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 6/205:29 pm
ORD
- GPT
1 stop6h 30m
American Airlines
Mon 6/226:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/15![American Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Wed 6/244:59 pm
ORD
- GPT
1 stop26h 11m
Multiple Airlines
Sun 6/287:50 pm
GPT
- ORD
2 stops20h 03m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$392
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 May 19, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
This Delta deal was found by Cheapflights users on 5/18. 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 5/2910:59 am
MDW
- GPT
1 stop6h 15m
Delta
Deal found 5/18![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 5/17. 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 5/247:05 am
ORD
- GPT
1 stop6h 59m
Delta
Deal found 5/17![Delta logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 6/57:29 am
ORD
- GPT
3 stops59h 41m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 5/17. 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 5/244:30 pm
MDW
- GPT
1 stop5h 21m
Delta
Deal found 5/17![Delta logo]()
$230
This Delta deal was found by Cheapflights users on 5/14. 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.
Tue 8/45:10 pm
MDW
- GPT
1 stop5h 11m
Delta
Deal found 5/14![Delta logo]()
$238
This United Airlines deal was found by Cheapflights users on 5/14. 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 8/48:51 am
ORD
- GPT
1 stop7h 20m
United Airlines
Deal found 5/14![United Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 5/14. 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.
Tue 8/46:00 am
ORD
- GPT
2 stops11h 15m
Delta
Deal found 5/14![Delta logo]()
$243
This American Airlines deal was found by Cheapflights users on 5/15. 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 6/55:34 pm
ORD
- GPT
1 stop6h 25m
American Airlines
Deal found 5/15![American Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Fri 5/298:05 am
ORD
- GPT
3 stops59h 05m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 5/16. 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.
Sat 5/231:50 pm
ORD
- GPT
2 stops29h 20m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 5/228:46 pm
ORD
- GPT
2 stops46h 24m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Fri 5/2912:04 pm
MDW
- GPT
3 stops55h 06m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$355
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 May 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (American Airlines) |
One-way from | $209 (Delta) |
Popular in | April |
Cheapest in | August |
Average price | $411 |
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 May 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
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 7/3
3:22 pm-8:41 pm
1 stop5h 19m
Gulfport Biloxi Regional
Mon 7/13
6:30 am-3:05 pm
2 stops8h 35m
$330
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 10/2
5:25 pm-10:06 pm
1 stop4h 41m
Gulfport Biloxi Regional
Tue 10/6
10:30 am-4:25 pm
1 stop5h 55m
$365
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 7/3
4:25 pm-8:41 pm
1 stop4h 16m
Gulfport Biloxi Regional
Mon 7/13
6:30 am-11:56 am
1 stop5h 26m
$374
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Mon 7/13
6:00 am-1:05 pm
1 stop7h 05m
Gulfport Biloxi Regional
Mon 7/20
6:30 am-11:56 am
1 stop5h 26m
$374
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 6/11
6:35 am-1:07 pm
1 stop6h 32m
Gulfport Biloxi Regional
Mon 6/15
1:53 pm-8:32 pm
1 stop6h 39m
$374
Quickest round-trip
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 7/17
12:41 pm-5:15 pm
1 stop4h 34m
Gulfport Biloxi Regional
Tue 7/21
6:00 pm-10:15 pm
1 stop4h 15m
$419
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Thu 9/17
1:05 pm-5:17 pm
1 stop4h 12m
Gulfport Biloxi Regional
Sun 9/20
6:00 am-12:30 pm
2 stops6h 30m
$423
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 5/21
5:30 am-1:25 pm
1 stop7h 55m
Gulfport Biloxi Regional
Sat 5/23
5:24 pm-11:15 pm
1 stop5h 51m
$440
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 6/30
5:10 am-10:14 am
1 stop5h 04m
Gulfport Biloxi Regional
Thu 7/2
6:32 pm-12:01 am
1 stop5h 29m
$484
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Tue 6/2
5:15 pm-9:51 pm
1 stop4h 36m
Gulfport Biloxi Regional
Sun 6/14
5:56 pm-10:17 pm
1 stop4h 21m
$517
Showing 1-10 of 30 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 May.
| 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 May is currently the most expensive (average of $398). 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 59% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 119 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 66% 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 May 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.
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
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 May 19, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on May 19, 2026.
Other flights from Chicago
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Popular flight searches
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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 2,558,603 searches. Data last updated May 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$323 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$416 | FlexibilityNo cancel fee | On-timeN/A |