HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Gulfport

$130+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 September 17, 2025.

Round-trip from

$227
(Kiwi.com)

One-way from

$130
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$358
From Chicago (CHI) to Gulfport Biloxi Regional
Search Deals
One-way flight from Chicago (CHI) to Gulfport Biloxi Regional
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Chicago to Gulfport

Cheapest flights from Chicago to Gulfport
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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:00 amORD - GPT
1 stop13h 15mMultiple Airlines
Thu 10/307:55 pmGPT - ORD
1 stop22h 51mMultiple Airlines
Deal found 9/16$227
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:20 amORD - GPT
1 stop8h 04mAmerican Airlines
Sun 11/234:54 pmGPT - ORD
1 stop7h 02mAmerican Airlines
Deal found 9/15$249
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:58 pmORD - GPT
1 stop24h 17mMultiple Airlines
Thu 10/167:55 pmGPT - ORD
1 stop25h 38mMultiple Airlines
Deal found 9/16$266
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:00 amORD - GPT
1 stop25h 59mMultiple Airlines
Sun 11/910:19 amGPT - ORD
1 stop6h 49mMultiple Airlines
Deal found 9/16$278
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:20 amORD - GPT
1 stop3h 56mDelta
Fri 10/246:05 pmGPT - ORD
1 stop5h 53mDelta
Deal found 9/14$279
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/274:25 pmMDW - GPT
1 stop5h 14mDelta
Tue 9/306:08 amGPT - MDW
1 stop5h 40mDelta
Deal found 9/15$284
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/273:45 pmORD - GPT
1 stop5h 54mDelta
Wed 10/16:04 pmGPT - ORD
1 stop4h 10mDelta
Deal found 9/16$284
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:20 amORD - GPT
1 stop3h 56mDelta
Tue 10/216:05 pmGPT - ORD
2 stops13h 45mDelta
Deal found 9/14$287
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:20 amORD - GPT
1 stop3h 58mDelta
Fri 10/176:05 pmGPT - ORD
1 stop5h 53mDelta
Deal found 9/16$294
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/125:20 amMDW - GPT
1 stop27h 39mMultiple Airlines
Sun 10/197:55 pmGPT - MDW
2 stops28h 29mMultiple Airlines
Deal found 9/16$303
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/274:25 pmMDW - GPT
1 stop5h 14mDelta
Wed 10/16:08 amGPT - MDW
1 stop5h 40mDelta
Deal found 9/14$309
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:25 amMDW - GPT
2 stops12h 50mMultiple Airlines
Sun 11/97:55 pmGPT - MDW
1 stop18h 36mMultiple Airlines
Deal found 9/16$357

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 September 17, 2025.
Use the filters below to find and compare flights from Chicago to Gulfport that are best for you.

Fly from

Chicago

Fly to

Gulfport

Route

Depart

Return

Price

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 10/26

6:00 am-7:15 pm

1 stop13h 15m

Gulfport Biloxi Regional

Thu 10/30

7:55 pm-6:46 pm

1 stop22h 51m

$227

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 11/20

8:20 am-4:24 pm

1 stop8h 04m

Gulfport Biloxi Regional

Sun 11/23

4:54 pm-11:56 pm

1 stop7h 02m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 10/14

5:20 am-9:16 am

1 stop3h 56m

Gulfport Biloxi Regional

Tue 10/21

6:05 pm-11:58 pm

1 stop5h 53m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 10/8

6:58 pm-7:15 pm

1 stop24h 17m

Gulfport Biloxi Regional

Thu 10/16

7:55 pm-9:33 pm

1 stop25h 38m

$266

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 10/14

5:20 am-9:16 am

1 stop3h 56m

Gulfport Biloxi Regional

Sat 10/18

10:03 am-5:00 pm

1 stop6h 57m

$279

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 10/14

5:20 am-9:16 am

1 stop3h 56m

Gulfport Biloxi Regional

Fri 10/24

6:05 pm-11:58 pm

1 stop5h 53m

$279

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 9/24

7:00 am-2:13 pm

1 stop7h 13m

Gulfport Biloxi Regional

Tue 9/30

2:00 pm-9:36 pm

1 stop7h 36m

$284

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 9/27

4:25 pm-9:39 pm

1 stop5h 14m

Gulfport Biloxi Regional

Tue 9/30

6:08 am-11:48 am

1 stop5h 40m

$284

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 9/27

3:45 pm-9:39 pm

1 stop5h 54m

Gulfport Biloxi Regional

Wed 10/1

6:04 pm-10:14 pm

1 stop4h 10m

$284

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 10/14

5:20 am-9:16 am

1 stop3h 56m

Gulfport Biloxi Regional

Thu 10/23

6:00 am-6:14 pm

2 stops12h 14m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 23 results
1
2
3

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.
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

What is the cheapest month to book a flight from Chicago to Gulfport?

Currently, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $417). 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?

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 September 17, 2025.
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.
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What airport do you fly into for flights to Gulfport from Chicago?

    Gulfport Biloxi Regional (GPT), located 3.1 mi from the city center, is the airport you fly into when you book flights from Chicago to Gulfport. 2 airlines have flights to Biloxi Regional from Chicago on a regular basis. Booking flights from Chicago to Gulfport Biloxi Regional should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Gulfport?

    American Airlines and Delta can get you from Chicago to Gulfport in just under 3h 56m. Your travel time can differ by up to 4h 08m. The distance from Chicago to Gulfport is about 802 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Gulfport round-trip?

    Flying on American Airlines is currently your cheapest option to Gulfport, with prices starting at $248. Another option worth looking into is Delta, starting at $253 round trip. You may be able to fly from Chicago to Gulfport for 37% less than the average price by searching for these airlines.

  • Can I find deals for flights from Chicago to Gulfport that include hotel bookings?

    Yes. In addition to deals on Chicago to Gulfport flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Gulfport?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Gulfport.

  • Can I find deals for business class flights from Chicago to Gulfport?

    Yes. Cheapflights offers flight deals from Chicago to Gulfport by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Gulfport?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $417). 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.

See more FAQs

Traveling to a place near Gulfport?

Book flights to Gulfport if you plan to visit one of these locations
Ocean Springs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Gulfport

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Memphis flights
Midway to Memphis flights
O'Hare Intl to Jackson flights
O'Hare Intl to Mobile flights
Midway to Jackson flights
O'Hare Intl to Baton Rouge flights
Midway to Baton Rouge flights
Moline to Mobile flights
St. Louis to Baton Rouge flights
Midway to Mobile flights
St. Louis to Mobile flights
O'Hare Intl to Gulfport flights
St. Louis to Memphis flights
Peoria to Mobile flights
St. Louis to Jackson flights
St. Louis to Gulfport flights
Peoria to Memphis flights
Midway to Gulfport flights
St. Louis to Alexandria flights
Moline to Baton Rouge flights
Moline to Memphis flights
Bloomington to Baton Rouge flights
Bloomington to Mobile flights
O'Hare Intl to Alexandria flights
Bloomington to Alexandria flights
Bloomington to Gulfport flights
O'Hare Intl to Meridian flights
Evansville to Baton Rouge flights
Midway to Alexandria flights
Peoria to Baton Rouge flights
O'Hare Intl to Columbus flights
Moline to Alexandria flights
Peoria to Alexandria flights
Springfield to Alexandria flights
Dubuque to Mobile flights

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$339FlexibilityNo cancel feeOn-time71%
DeltaCheapest$253Average$423FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.