$182+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Jun 24 — Jul 11
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 25, 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 25, 2026.
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:25 pm
MDW
- GPT
1 stop4h 42m
Delta
Sat 11/76:00 am
GPT
- MDW
1 stop5h 56m
Delta
Deal found 5/21![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/33:35 pm
ORD
- GPT
1 stop6h 32m
Delta
Sat 11/710:30 am
GPT
- ORD
1 stop6h 07m
Delta
Deal found 5/21![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:25 pm
MDW
- GPT
1 stop4h 41m
Delta
Tue 10/66:00 am
GPT
- MDW
1 stop5h 56m
Delta
Deal found 5/22![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 11/25:30 am
ORD
- GPT
1 stop4h 09m
Delta
Tue 11/102:15 pm
GPT
- ORD
1 stop4h 17m
Delta
Deal found 5/21![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:15 am
ORD
- GPT
1 stop5h 20m
Delta
Sat 11/76:00 am
GPT
- ORD
2 stops6h 37m
Delta
Deal found 5/21![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 11/55:30 am
ORD
- GPT
1 stop4h 09m
Delta
Mon 11/96:00 am
GPT
- ORD
1 stop6h 06m
Delta
Deal found 5/21![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 9/66:00 am
ORD
- GPT
2 stops7h 33m
Delta
Sun 9/136:00 am
GPT
- ORD
2 stops6h 39m
Delta
Deal found 5/21![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 11/510:35 am
MDW
- GPT
1 stop6h 42m
Delta
Sun 11/86:00 am
GPT
- MDW
2 stops6h 33m
Delta
Deal found 5/20![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 11/51:35 pm
ORD
- GPT
2 stops8h 32m
Delta
Sun 11/86:00 am
GPT
- ORD
2 stops10h 33m
Delta
Deal found 5/20![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:56 am
MDW
- GPT
1 stop4h 04m
Delta
Wed 9/165:59 pm
GPT
- MDW
1 stop4h 26m
Delta
Deal found 5/24![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:34 pm
ORD
- GPT
1 stop6h 25m
American Airlines
Sat 6/276:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/24![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/125:34 pm
ORD
- GPT
1 stop6h 25m
American Airlines
Tue 6/166:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/21![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 25, 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 25, 2026.
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:10 pm
MDW
- GPT
1 stop4h 58m
Delta
Tue 10/66:00 am
GPT
- MDW
1 stop5h 56m
Delta
Deal found 5/25![Delta logo]()
$300
This American Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:34 pm
ORD
- GPT
1 stop6h 25m
American Airlines
Sat 6/276:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/24![American Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:35 am
ORD
- GPT
1 stop6h 30m
Delta
Mon 7/206:30 am
GPT
- ORD
1 stop6h 04m
Delta
Deal found 5/25![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:20 pm
ORD
- GPT
2 stops42h 51m
United Airlines
Sat 6/275:19 pm
GPT
- ORD
1 stop7h 26m
United Airlines
Deal found 5/23![United Airlines logo]()
$679
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:45 am
ORD
- GPT
1 stop7h 30m
Delta
Tue 7/216:00 pm
GPT
- ORD
1 stop5h 53m
Delta
Deal found 5/22![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/163:22 pm
ORD
- GPT
1 stop6h 52m
Delta
Mon 7/206:30 am
GPT
- ORD
1 stop6h 04m
Delta
Deal found 5/23![Delta logo]()
$378
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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
Tue 6/1610:06 am
GPT
- ORD
2 stops12h 28m
Delta
Deal found 5/21![Delta logo]()
$383
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:10 pm
MDW
- GPT
1 stop5h 04m
Delta
Tue 7/216:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 5/22![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/141:49 pm
MDW
- GPT
2 stops8h 25m
Delta
Sun 7/196:30 am
GPT
- MDW
1 stop5h 26m
Delta
Deal found 5/20![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/1211:05 am
MDW
- GPT
1 stop6h 06m
Delta
Tue 6/165:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 5/21![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:48 am
MDW
- GPT
1 stop6h 26m
Delta
Sun 10/45:59 pm
GPT
- MDW
1 stop4h 26m
Delta
Deal found 5/23![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:05 am
ORD
- GPT
2 stops10h 06m
Delta
Tue 6/235:56 pm
GPT
- ORD
1 stop6h 03m
Delta
Deal found 5/22![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/96:05 am
MDW
- GPT
1 stop6h 58m
Delta
Fri 8/146:01 pm
GPT
- MDW
1 stop4h 35m
Delta
Deal found 5/20![Delta logo]()
$513
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:00 am
MDW
- GPT
1 stop7h 05m
Delta
Mon 7/206:00 pm
GPT
- MDW
1 stop4h 15m
Delta
Deal found 5/25![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/118:08 am
ORD
- GPT
1 stop4h 59m
Delta
Tue 6/1610:06 am
GPT
- ORD
2 stops12h 28m
Delta
Deal found 5/21![Delta logo]()
$659
Last-minute flights from Chicago to GulfportDiscover last-minute flight deals from Chicago to Gulfport. Data last updated May 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulfport. Data last updated May 25, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- GPT
1 stop7h 07m
Delta
Tue 6/165:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 5/21![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/155:56 pm
GPT
- ORD
1 stop6h 03m
Delta
Deal found 5/20![Delta logo]()
$378
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/125:34 pm
ORD
- GPT
1 stop6h 25m
American Airlines
Tue 6/166:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/21![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/126:47 pm
ORD
- GPT
1 stop5h 12m
American Airlines
Mon 6/156:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/20![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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
Tue 6/1610:06 am
GPT
- ORD
2 stops12h 28m
Delta
Deal found 5/21![Delta logo]()
$383
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/135:00 am
ORD
- GPT
1 stop5h 50m
American Airlines
Tue 6/166:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/21![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/136:35 am
ORD
- GPT
1 stop7h 09m
Delta
Tue 6/1610:06 am
GPT
- ORD
2 stops12h 28m
Delta
Deal found 5/21![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:00 am
ORD
- GPT
1 stop5h 52m
American Airlines
Tue 6/236:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/22![American Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/176:00 am
MDW
- GPT
1 stop7h 07m
Delta
Tue 6/235:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 5/21![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/185:11 pm
MDW
- GPT
1 stop5h 06m
Delta
Wed 6/245:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 5/20![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:11 pm
MDW
- GPT
1 stop5h 06m
Delta
Tue 6/235:56 pm
GPT
- MDW
1 stop4h 21m
Delta
Deal found 5/22![Delta logo]()
$334
This American Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:34 pm
ORD
- GPT
1 stop6h 25m
American Airlines
Sat 6/276:38 pm
GPT
- ORD
1 stop5h 20m
American Airlines
Deal found 5/24![American Airlines logo]()
$325
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 25, 2026.
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/27:52 am
ORD
- GPT
2 stops23h 49m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 5/297:07 am
ORD
- GPT
1 stop6h 02m
Delta
Deal found 5/21![Delta logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/261:50 pm
ORD
- GPT
2 stops17h 51m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/25:45 pm
ORD
- GPT
1 stop6h 11m
American Airlines
Deal found 5/21![American Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/212:27 pm
MDW
- GPT
2 stops19h 14m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:00 am
ORD
- GPT
1 stop5h 55m
American Airlines
Deal found 5/24![American Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:11 pm
MDW
- GPT
1 stop5h 06m
Delta
Deal found 5/22![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/128:08 am
ORD
- GPT
1 stop4h 59m
Delta
Deal found 5/21![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/121:29 pm
ORD
- GPT
3 stops53h 41m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:23 pm
MDW
- GPT
3 stops58h 18m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:05 am
ORD
- GPT
3 stops59h 05m
Multiple Airlines
Deal found 5/23![Multiple Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/127:55 pm
ORD
- GPT
2 stops20h 16m
United Airlines
Deal found 5/22![United Airlines logo]()
$406
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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Delta) |
One-way from | $182 (Kiwi.com) |
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 25, 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
Fri 10/2
5:10 pm-10:08 pm
1 stop4h 58m
Gulfport Biloxi Regional
Tue 10/6
6:00 am-11:56 am
1 stop5h 56m
$300
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 6/26
5:34 pm-11:59 pm
1 stop6h 25m
Gulfport Biloxi Regional
Sat 6/27
6:38 pm-11:58 pm
1 stop5h 20m
$325
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Mon 7/13
6:35 am-1:05 pm
1 stop6h 30m
Gulfport Biloxi Regional
Mon 7/20
6:30 am-12:34 pm
1 stop6h 04m
$334
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 7/17
9:45 am-5:15 pm
1 stop7h 30m
Gulfport Biloxi Regional
Tue 7/21
6:00 pm-11:53 pm
1 stop5h 53m
$369
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Thu 7/16
3:22 pm-10:14 pm
1 stop6h 52m
Gulfport Biloxi Regional
Mon 7/20
6:30 am-12:34 pm
1 stop6h 04m
$378
ChicagoGulfport
ORD - GPT
ORDGPT
Chicago O'Hare Intl
Fri 6/12
6:35 am-1:07 pm
1 stop6h 32m
Gulfport Biloxi Regional
Tue 6/16
10:06 am-10:34 pm
2 stops12h 28m
$383
Quickest round-trip
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 7/17
5:10 pm-10:14 pm
1 stop5h 04m
Gulfport Biloxi Regional
Tue 7/21
6:00 pm-10:15 pm
1 stop4h 15m
$409
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Tue 7/14
1:49 pm-10:14 pm
2 stops8h 25m
Gulfport Biloxi Regional
Sun 7/19
6:30 am-11:56 am
1 stop5h 26m
$414
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Fri 6/12
11:05 am-5:11 pm
1 stop6h 06m
Gulfport Biloxi Regional
Tue 6/16
5:56 pm-10:17 pm
1 stop4h 21m
$423
ChicagoGulfport
MDW - GPT
MDWGPT
Chicago Midway
Thu 10/1
10:48 am-5:14 pm
1 stop6h 26m
Gulfport Biloxi Regional
Sun 10/4
5:59 pm-10:25 pm
1 stop4h 26m
$447
Showing 1-10 of 27 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 25, 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.
Comfort
7.8
Overall
7.9
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Overall
7.9
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Overall
7.9
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
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 25, 2026.
Chicago and Gulfport flights
Browse other Chicago and Gulfport flight options. Last updated on May 25, 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 May 25, 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 May 25, 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 |