$153+ Cheap flights from Gulfport (GPT) to Chicago (CHI)
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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Gulfport to Chicago 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
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Cheapest flights from Gulfport to ChicagoExplore the most affordable flight options available from Gulfport to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Gulfport to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/16:09 pm -
1 stop4h 45m
Tue 12/86:00 am -
1 stop7h 11m
Deal found 10/31![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/54:00 pm -
1 stop4h 53m
Sat 12/121:34 pm -
1 stop7h 19m
Deal found 11/4![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/16:09 pm -
1 stop5h 47m
Tue 12/811:35 am -
2 stops10h 22m
Deal found 10/31![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/31:54 pm -
1 stop5h 15m
Wed 12/910:36 am -
1 stop6h 48m
Deal found 11/2![Delta logo]()
$330
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/210:04 am -
2 stops8h 22m
Wed 12/911:35 am -
2 stops10h 22m
Deal found 11/2![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/116:09 pm -
1 stop4h 45m
Sun 12/136:00 am -
1 stop7h 07m
Deal found 10/31![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/111:52 pm -
1 stop5h 17m
Fri 12/186:49 am -
1 stop6h 17m
Deal found 10/30![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/206:28 pm -
1 stop5h 52m
Mon 11/234:58 pm -
1 stop7h 03m
Deal found 11/2![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/116:09 pm -
1 stop4h 45m
Fri 12/186:00 am -
1 stop7h 06m
Deal found 10/30![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/206:04 pm -
1 stop5h 50m
Mon 11/232:44 pm -
2 stops7h 08m
Deal found 11/2![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/136:04 pm -
1 stop4h 50m
Mon 11/165:13 pm -
1 stop4h 39m
Deal found 10/30![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/175:19 am -
1 stop5h 43m
Sat 11/216:49 pm -
1 stop5h 12m
Deal found 11/2![American Airlines logo]()
$369
Best flights from Gulfport to ChicagoDiscover carefully curated flight deals from Gulfport to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Gulfport to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/16:09 pm -
1 stop4h 45m
Tue 12/86:00 am -
1 stop7h 11m
Deal found 10/31![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/96:32 am -
1 stop7h 47m
Sat 12/124:00 pm -
1 stop7h 30m
Deal found 11/3![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/116:46 pm -
2 stops19h 44m
Sun 12/138:00 am -
1 stop24h 51m
Deal found 10/31![Multiple Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/16:09 pm -
1 stop5h 47m
Tue 12/811:35 am -
2 stops10h 22m
Deal found 10/31![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/54:00 pm -
1 stop4h 53m
Sat 12/129:59 am -
2 stops10h 54m
Deal found 11/4![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 11/206:28 pm -
1 stop5h 52m
Mon 11/234:58 pm -
1 stop7h 03m
Deal found 11/4![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/210:04 am -
2 stops8h 22m
Wed 12/911:35 am -
2 stops10h 22m
Deal found 11/2![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/111:52 pm -
1 stop5h 17m
Fri 12/186:49 am -
1 stop6h 17m
Deal found 10/30![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/206:04 pm -
1 stop5h 50m
Mon 11/232:44 pm -
2 stops7h 08m
Deal found 11/1![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/146:26 am -
2 stops10h 13m
Wed 11/186:00 am -
1 stop7h 04m
Deal found 10/30![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/136:04 pm -
1 stop4h 50m
Mon 11/165:13 pm -
1 stop4h 39m
Deal found 10/31![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/126:04 pm -
1 stop4h 50m
Mon 11/1610:34 am -
2 stops11h 18m
Deal found 11/2![Delta logo]()
$404
Last-minute flights from Gulfport to ChicagoDiscover last-minute flight deals from Gulfport to Chicago. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Gulfport to Chicago. Data last updated November 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/136:04 pm -
1 stop4h 50m
Mon 11/165:13 pm -
1 stop4h 39m
Deal found 10/30![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/175:19 am -
1 stop5h 43m
Sat 11/216:49 pm -
1 stop5h 12m
Deal found 11/2![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/206:28 pm -
1 stop5h 52m
Mon 11/234:58 pm -
1 stop7h 03m
Deal found 11/2![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/206:04 pm -
1 stop5h 50m
Mon 11/232:44 pm -
2 stops7h 08m
Deal found 11/2![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/16:09 pm -
1 stop4h 45m
Tue 12/86:00 am -
1 stop7h 11m
Deal found 10/31![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/16:09 pm -
1 stop5h 47m
Tue 12/811:35 am -
2 stops10h 22m
Deal found 10/31![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/210:04 am -
2 stops8h 22m
Wed 12/911:35 am -
2 stops10h 22m
Deal found 11/2![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/31:54 pm -
1 stop5h 15m
Wed 12/910:36 am -
1 stop6h 48m
Deal found 11/2![Delta logo]()
$330
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/54:00 pm -
1 stop4h 53m
Sat 12/121:34 pm -
1 stop7h 19m
Deal found 11/4![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/116:09 pm -
1 stop4h 45m
Sun 12/136:00 am -
1 stop7h 07m
Deal found 10/31![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/111:52 pm -
1 stop5h 17m
Fri 12/186:49 am -
1 stop6h 17m
Deal found 10/30![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/116:09 pm -
1 stop4h 45m
Fri 12/186:00 am -
1 stop7h 06m
Deal found 10/30![Delta logo]()
$359
One-way flights from Gulfport to ChicagoSearch for one-way flight options from Gulfport to Chicago. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Gulfport to Chicago. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/116:46 pm -
2 stops27h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/137:45 pm -
2 stops39h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Mon 11/166:46 pm -
3 stops53h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/116:46 pm -
3 stops16h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Mon 11/166:46 pm -
3 stops47h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/136:46 pm -
2 stops20h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 2/101:53 pm -
1 stop5h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![American Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 2/106:00 am -
2 stops11h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Delta logo]()
$211
This Trip.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:45 pm -
1 stop13h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/116:09 pm -
1 stop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Delta logo]()
$221
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/116:23 pm -
1 stop5h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/136:15 am -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$226
Find flight deals from Gulfport to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Gulfport (GPT) to Chicago (CHI). 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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Delta) |
One-way from | $153 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Gulfport to Chicago 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 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Gulfport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Fri 12/11
6:46 pm-10:00 pm
2 stops27h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$153
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Fri 12/11
6:46 pm-11:33 am
3 stops16h 47m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$186
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Wed 2/10
6:00 am-5:19 pm
2 stops11h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$211
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Sun 12/13
6:15 am-12:04 pm
1 stop5h 49m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$221
Quickest round-trip
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Fri 12/11
6:09 pm-10:54 pm
1 stop4h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$221
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Tue 11/10
6:45 am-12:19 pm
1 stop5h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$297
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Sat 11/7
4:00 pm-10:33 pm
1 stop6h 33m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$297
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Tue 11/10
10:04 am-4:18 pm
1 stop6h 14m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$297
GulfportChicago
GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl
GPTORD
Gulfport Biloxi Regional
Wed 11/11
1:50 pm-8:49 pm
1 stop6h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$297
GulfportChicago
GPT Gulfport Biloxi Regional - MDW Chicago Midway
GPTMDW
Gulfport Biloxi Regional
Sat 11/14
6:26 am-4:39 pm
2 stops10h 13m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$302
Showing 1-10 of 28 resultsSorted by cheapest first
Compare providers for flights from Gulfport to Chicago
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 Gulfport to Chicago in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Gulfport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Gulfport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Gulfport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Gulfport-Chicago 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 Gulfport-Chicago 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 Gulfport to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Gulfport with our price prediction graph.
GPT-CHI
GPT-MDW
GPT-ORD
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 Gulfport to Chicago
GPT-CHI
GPT-MDW
GPT-ORD
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 4, 2026.
See what other customers who have flown with American Airlines from Gulfport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.4
Comfort
7.2
Overall
7.0
Food
6.4
Entertainment
6.8
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Boarding
7.4
Comfort
7.2
Overall
7.0
Food
6.4
Entertainment
6.8
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Related info for your journey
Find useful and relevant information for your journey from Gulfport to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Gulfport and Chicago flights
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Other flights from Gulfport
Browse through other flights departing from Gulfport. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.
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Top airline flying from Gulfport to Chicago
Discover the top airline that operate flights from Gulfport to Chicago. 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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$309 | Average$460 | FlexibilityNo cancel fee | On-time71% |