$238+ Cheap flights from Chicago (CHI) to Gulfport (GPT)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
May 13 — May 201
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 13, 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 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/38:52 pm
ORD
- GPT
1 stop12h 08m
Multiple Airlines
Thu 5/77:50 pm
GPT
- ORD
1 stop27h 23m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 5/76:00 am
MDW
- GPT
2 stops25h 41m
Multiple Airlines
Thu 5/147:50 pm
GPT
- MDW
1 stop20h 07m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/38:39 am
MDW
- GPT
1 stop10h 01m
Multiple Airlines
Thu 5/77:50 pm
GPT
- MDW
1 stop20h 07m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 4/8. 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 5/165:00 am
ORD
- GPT
1 stop5h 33m
American Airlines
Tue 5/195:03 pm
GPT
- ORD
1 stop6h 45m
American Airlines
Deal found 4/8![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 4/8. 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 4/8![American Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 5/1010:49 am
ORD
- GPT
1 stop8h 21m
Multiple Airlines
Sun 5/177:50 pm
GPT
- ORD
2 stops36h 05m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 6/2510:27 am
ORD
- GPT
1 stop8h 43m
Multiple Airlines
Mon 6/295:31 pm
GPT
- ORD
2 stops38h 32m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 4/10. 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 4/256:41 pm
ORD
- GPT
1 stop5h 17m
American Airlines
Tue 4/286:03 am
GPT
- ORD
1 stop6h 33m
American Airlines
Deal found 4/10![American Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 4/8. 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
Mon 4/276:54 pm
GPT
- MDW
2 stops27h 20m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 6/48:30 am
ORD
- GPT
1 stop23h 11m
Multiple Airlines
Mon 6/85:31 pm
GPT
- ORD
2 stops38h 32m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 4/233:08 pm
ORD
- GPT
1 stop17h 52m
Multiple Airlines
Mon 4/276:54 pm
GPT
- ORD
1 stop23h 26m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 4/10. 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 7/265:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Sat 8/13:00 pm
GPT
- MDW
1 stop7h 15m
Delta
Deal found 4/10![Delta logo]()
$365
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 13, 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 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/38:39 am
MDW
- GPT
1 stop10h 01m
Multiple Airlines
Thu 5/77:50 pm
GPT
- MDW
1 stop20h 07m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/12. 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 4/255:15 am
ORD
- GPT
1 stop4h 09m
Delta
Tue 4/282:40 pm
GPT
- ORD
1 stop5h 36m
Delta
Deal found 4/12![Delta logo]()
$365
This United Airlines deal was found by Cheapflights users on 4/8. 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 5/512:40 pm
ORD
- GPT
1 stop7h 13m
United Airlines
Sat 5/94:55 pm
GPT
- ORD
1 stop7h 50m
United Airlines
Deal found 4/8![United Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 4/9. 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 5/86:23 am
MDW
- GPT
1 stop6h 46m
Delta
Tue 5/121:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/9![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 4/12. 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 4/285:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Sat 5/210:09 am
GPT
- MDW
1 stop6h 17m
Delta
Deal found 4/12![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 4/9. 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 4/9![Delta logo]()
$384
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
ORD
- GPT
2 stops13h 53m
United Airlines
Wed 5/134:55 pm
GPT
- ORD
1 stop7h 50m
United Airlines
Deal found 4/7![United Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 4/12. 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 5/117:07 am
ORD
- GPT
1 stop6h 02m
Delta
Mon 5/186:02 pm
GPT
- ORD
1 stop5h 57m
Delta
Deal found 4/12![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 4/7. 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 5/65:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Wed 5/131:55 pm
GPT
- MDW
1 stop7h 14m
Delta
Deal found 4/7![Delta logo]()
$425
This United Airlines deal was found by Cheapflights users on 4/10. 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 5/118:03 pm
ORD
- GPT
2 stops23h 50m
United Airlines
Sat 5/164:55 pm
GPT
- ORD
1 stop6h 20m
United Airlines
Deal found 4/10![United Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 4/11. 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 4/259:48 am
ORD
- GPT
1 stop4h 18m
Delta
Sun 4/262:40 pm
GPT
- ORD
1 stop5h 36m
Delta
Deal found 4/11![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 4/8. 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 5/86:00 pm
ORD
- GPT
2 stops19h 21m
United Airlines
Tue 5/122:00 pm
GPT
- ORD
1 stop7h 51m
United Airlines
Deal found 4/8![United Airlines logo]()
$591
This United Airlines deal was found by Cheapflights users on 4/9. 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 4/248:05 pm
ORD
- GPT
2 stops18h 08m
United Airlines
Tue 4/284:26 pm
GPT
- ORD
1 stop6h 49m
United Airlines
Deal found 4/9![United Airlines logo]()
$611
This Delta deal was found by Cheapflights users on 4/11. 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 7/23:00 pm
GPT
- ORD
1 stop5h 32m
Delta
Deal found 4/11![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 4/12. 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 4/175:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Mon 4/205:55 pm
GPT
- MDW
1 stop4h 33m
Delta
Deal found 4/12![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 4/10. 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 6/265:11 pm
MDW
- GPT
1 stop5h 06m
Delta
Sun 6/286:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/10![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 4/10. 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 4/255:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Tue 4/285:55 pm
GPT
- MDW
1 stop4h 33m
Delta
Deal found 4/10![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 4/8. 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 4/2312:52 pm
MDW
- GPT
1 stop4h 17m
Delta
Mon 4/275:55 pm
GPT
- MDW
1 stop4h 33m
Delta
Deal found 4/8![Delta logo]()
$739
This Delta deal was found by Cheapflights users on 4/10. 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 6/265:11 pm
MDW
- GPT
1 stop5h 06m
Delta
Mon 6/2910:06 am
GPT
- MDW
1 stop6h 40m
Delta
Deal found 4/10![Delta logo]()
$758
This Delta deal was found by Cheapflights users on 4/10. 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
Tue 6/96:01 pm
GPT
- MDW
1 stop4h 16m
Delta
Deal found 4/10![Delta logo]()
$761
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated April 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated April 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/8. 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
Mon 4/276:54 pm
GPT
- MDW
2 stops27h 20m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 4/233:08 pm
ORD
- GPT
1 stop17h 52m
Multiple Airlines
Mon 4/276:54 pm
GPT
- ORD
1 stop23h 26m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 4/9. 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 4/246:41 pm
ORD
- GPT
1 stop5h 17m
American Airlines
Tue 4/285:49 pm
GPT
- ORD
1 stop6h 05m
American Airlines
Deal found 4/9![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 4/10. 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 4/256:41 pm
ORD
- GPT
1 stop5h 17m
American Airlines
Tue 4/286:03 am
GPT
- ORD
1 stop6h 33m
American Airlines
Deal found 4/10![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 4/12. 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 4/255:15 am
ORD
- GPT
1 stop4h 09m
Delta
Tue 4/282:40 pm
GPT
- ORD
1 stop5h 36m
Delta
Deal found 4/12![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 4/12. 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 4/285:21 pm
MDW
- GPT
1 stop4h 52m
Delta
Sat 5/210:09 am
GPT
- MDW
1 stop6h 17m
Delta
Deal found 4/12![Delta logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/38:52 pm
ORD
- GPT
1 stop12h 08m
Multiple Airlines
Thu 5/77:50 pm
GPT
- ORD
1 stop27h 23m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/38:39 am
MDW
- GPT
1 stop10h 01m
Multiple Airlines
Thu 5/77:50 pm
GPT
- MDW
1 stop20h 07m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 5/76:00 am
MDW
- GPT
2 stops25h 41m
Multiple Airlines
Thu 5/147:50 pm
GPT
- MDW
1 stop20h 07m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 5/1010:49 am
ORD
- GPT
1 stop8h 21m
Multiple Airlines
Sun 5/177:50 pm
GPT
- ORD
2 stops36h 05m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 4/8. 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 4/8![American Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 4/8. 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 5/165:00 am
ORD
- GPT
1 stop5h 33m
American Airlines
Tue 5/195:03 pm
GPT
- ORD
1 stop6h 45m
American Airlines
Deal found 4/8![American Airlines logo]()
$291
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 13, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated April 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/316:00 am
MDW
- GPT
2 stops25h 41m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 4/12. 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 5/1511:26 am
ORD
- GPT
1 stop5h 48m
Delta
Deal found 4/12![Delta logo]()
$250
This Delta deal was found by Cheapflights users on 4/12. 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 5/1510:59 am
MDW
- GPT
1 stop6h 15m
Delta
Deal found 4/12![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/8. 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
Deal found 4/8![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 4/157:15 pm
ORD
- GPT
3 stops37h 45m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 4/11. 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 4/274:40 pm
ORD
- GPT
1 stop6h 11m
American Airlines
Deal found 4/11![American Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 4/12. 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 5/152:41 pm
ORD
- GPT
2 stops9h 17m
American Airlines
Deal found 4/12![American Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:05 pm
ORD
- GPT
1 stop7h 40m
United Airlines
Deal found 4/8![United Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 4/11. 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 4/155:15 am
ORD
- GPT
1 stop4h 09m
Delta
Deal found 4/11![Delta logo]()
$418
This United Airlines deal was found by Cheapflights users on 4/11. 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 4/279:45 pm
ORD
- GPT
2 stops16h 28m
United Airlines
Deal found 4/11![United Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/158:56 pm
ORD
- GPT
3 stops46h 14m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 4/12![Multiple Airlines logo]()
$691
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 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $238 (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 13, 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
Sun 5/3
8:39 am-6:40 pm
1 stop10h 01m
Gulfport Biloxi Regional
Thu 5/7
7:50 pm-3:57 pm
1 stop20h 07m
$289
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sat 4/25
5:15 am-9:24 am
1 stop4h 09m
Gulfport Biloxi Regional
Tue 4/28
2:40 pm-8:16 pm
1 stop5h 36m
$365
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 5/8
6:23 am-1:09 pm
1 stop6h 46m
Gulfport Biloxi Regional
Tue 5/12
1:55 pm-9:09 pm
1 stop7h 14m
$369
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Tue 4/28
5:21 pm-10:13 pm
1 stop4h 52m
Gulfport Biloxi Regional
Sat 5/2
10:09 am-4:26 pm
1 stop6h 17m
$369
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
$384
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Mon 5/11
7:07 am-1:09 pm
1 stop6h 02m
Gulfport Biloxi Regional
Mon 5/18
6:02 pm-11:59 pm
1 stop5h 57m
$409
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Tue 5/5
12:40 pm-7:53 pm
1 stop7h 13m
Gulfport Biloxi Regional
Sat 5/9
4:55 pm-12:45 am
1 stop7h 50m
$421
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Wed 5/6
5:21 pm-10:13 pm
1 stop4h 52m
Gulfport Biloxi Regional
Wed 5/13
1:55 pm-9:09 pm
1 stop7h 14m
$425
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Sat 4/25
9:48 am-2:06 pm
1 stop4h 18m
Gulfport Biloxi Regional
Sun 4/26
2:40 pm-8:16 pm
1 stop5h 36m
$433
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
3:00 pm-8:32 pm
1 stop5h 32m
$469
Showing 1-10 of 32 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
MDW-GPT
ORD-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
MDW-GPT
ORD-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 $71). Flying from Chicago to Gulfport in July is currently the most expensive (average of $164). 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 13, 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.
Food
7.2
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Crew
8.5
Overall
7.9
Comfort
7.9
Boarding
8.1
Entertainment
7.8
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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Complete your trip
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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 13, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on April 13, 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 April 13, 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 April 13, 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 |