HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Gulfport

$122+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
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 November 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$122
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$461
Provider with most accurate pricing for Chicago (CHI)-Gulfport Biloxi Regional flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Gulfport Biloxi Regional flights.
Search Deals
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. 18% potential increase in price ($99 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 18, 2025.

This Delta deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:29 pmMDW - GPT
1 stop4h 34mDelta
Mon 12/225:21 pmGPT - MDW
1 stop5h 01mDelta
Deal found 11/16$249
This Delta deal was found by Cheapflights users on 11/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:30 amORD - GPT
1 stop4h 20mDelta
Mon 12/225:21 pmGPT - ORD
1 stop6h 41mDelta
Deal found 11/16$249
This Kiwi.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/34:01 pmORD - GPT
2 stops27h 14mMultiple Airlines
Sun 12/77:55 pmGPT - ORD
1 stop17h 21mMultiple Airlines
Deal found 11/18$276
This Delta deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:13 pmMDW - GPT
1 stop4h 50mDelta
Sat 12/610:35 amGPT - MDW
1 stop5h 09mDelta
Deal found 11/17$279
This Delta deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/29:49 amORD - GPT
1 stop4h 19mDelta
Sat 12/63:30 pmGPT - ORD
1 stop7h 13mDelta
Deal found 11/17$279
This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:11 amORD - GPT
1 stop5h 05mAmerican Airlines
Thu 12/257:05 amGPT - ORD
2 stops8h 22mAmerican Airlines
Deal found 11/18$299
This Delta deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:59 pmORD - GPT
1 stop4h 04mDelta
Sun 12/285:21 pmGPT - ORD
1 stop6h 42mDelta
Deal found 11/17$304
This KAYAK deal was found by Cheapflights users on 11/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1612:50 pmMDW - GPT
1 stop4h 26mDelta
Mon 12/225:21 pmGPT - MDW
1 stop5h 01mDelta
Deal found 11/16$313
This KAYAK deal was found by Cheapflights users on 11/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:30 amORD - GPT
1 stop4h 20mDelta
Sun 12/215:21 pmGPT - ORD
1 stop6h 41mDelta
Deal found 11/16$313
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/243:51 pmORD - GPT
2 stops27h 19mMultiple Airlines
Fri 12/266:51 pmGPT - ORD
1 stop5h 54mMultiple Airlines
Deal found 11/16$323
This KAYAK deal was found by Cheapflights users on 11/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:31 amORD - GPT
2 stops11h 02mAmerican Airlines
Sun 12/212:32 pmGPT - ORD
1 stop7h 48mAmerican Airlines
Deal found 11/16$324
This KAYAK deal was found by Cheapflights users on 11/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1612:50 pmMDW - GPT
1 stop4h 26mDelta
Sun 12/215:21 pmGPT - MDW
1 stop5h 01mDelta
Deal found 11/16$338

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 November 18, 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

MDW - GPT

MDWGPT

Chicago Midway

Mon 12/15

5:29 pm-10:03 pm

1 stop4h 34m

Gulfport Biloxi Regional

Mon 12/22

5:21 pm-10:22 pm

1 stop5h 01m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 12/19

5:59 pm-10:03 pm

1 stop4h 04m

Gulfport Biloxi Regional

Fri 12/26

5:21 pm-12:03 am

1 stop6h 42m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/7

9:55 am-3:09 pm

1 stop5h 14m

Gulfport Biloxi Regional

Sat 1/10

6:05 am-1:39 pm

1 stop7h 34m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 12/15

5:30 am-9:50 am

1 stop4h 20m

Gulfport Biloxi Regional

Mon 12/22

5:21 pm-12:02 am

1 stop6h 41m

$249

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 1/10

5:31 pm-9:53 pm

1 stop4h 22m

Gulfport Biloxi Regional

Thu 1/15

4:00 pm-10:07 pm

1 stop6h 07m

$274

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Wed 1/28

7:05 am-1:51 pm

1 stop6h 46m

Gulfport Biloxi Regional

Sun 2/1

6:08 pm-11:56 pm

1 stop5h 48m

$274

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 12/3

12:50 pm-5:16 pm

1 stop4h 26m

Gulfport Biloxi Regional

Sun 12/7

6:00 am-11:55 am

1 stop5h 55m

$279

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 12/2

5:13 pm-10:03 pm

1 stop4h 50m

Gulfport Biloxi Regional

Sat 12/6

10:35 am-3:44 pm

1 stop5h 09m

$279

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 12/2

9:49 am-2:08 pm

1 stop4h 19m

Gulfport Biloxi Regional

Sat 12/6

3:30 pm-10:43 pm

1 stop7h 13m

$279

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 12/19

5:59 pm-10:03 pm

1 stop4h 04m

Gulfport Biloxi Regional

Sun 12/28

5:21 pm-12:03 am

1 stop6h 42m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

Showing 1-10 of 35 results
1
2
3
4

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Gulfport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Gulfport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.
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, June is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $80). Flying from Chicago to Gulfport in July is currently the most expensive (average of $161). 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.

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 November 18, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, 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
7.9
Good
8,003 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,003 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,019 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,045 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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?

    Delta can get you from Chicago to Gulfport in just under 4h 34m. Your travel time can differ by up to . The distance from Chicago to Gulfport is about 789 mi.

  • 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 $248 round trip. You may be able to fly from Chicago to Gulfport for 41% 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, June is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $80). Flying from Chicago to Gulfport in July is currently the most expensive (average of $161). 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 Mobile flights
Midway to Mobile flights
O'Hare Intl to Jackson flights
O'Hare Intl to Baton Rouge flights
O'Hare Intl to Gulfport flights
Midway to Jackson flights
Midway to Baton Rouge flights
St. Louis to Gulfport flights
St. Louis to Mobile flights
St. Louis to Jackson flights
St. Louis to Baton Rouge flights
St. Louis to Memphis flights
O'Hare Intl to Alexandria flights
Peoria to Baton Rouge flights
Midway to Gulfport flights
Moline to Memphis flights
Moline to Mobile flights
Bloomington to Alexandria flights
Midway to Alexandria flights
O'Hare Intl to Columbus flights
Evansville to Baton Rouge flights
Peoria to Memphis flights
Moline to Alexandria flights
O'Hare Intl to Meridian flights
Peoria to Mobile flights
Moline to Baton Rouge flights
St. Louis to Alexandria flights
Bloomington to Mobile flights
Peoria to Alexandria flights
Bloomington to Gulfport flights
Springfield to Alexandria flights
Dubuque to Mobile flights
Bloomington to Baton Rouge 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 November 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$336FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$415FlexibilityNo 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.