HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Gulfport

$153+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GPT
Apr 30 — May 71
Thu 4/30
Thu 5/7
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

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 March 31, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/125:25 am
ORD
-
GPT
1 stop27h 35m
Multiple Airlines
Thu 4/167:20 pm
GPT
-
ORD
2 stops15h 03m
Multiple Airlines
Deal found 3/28$246
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
MDW
-
GPT
2 stops12h 40m
Multiple Airlines
Sun 4/197:20 pm
GPT
-
MDW
1 stop12h 44m
Multiple Airlines
Deal found 3/28$274
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:40 am
ORD
-
GPT
1 stop12h 00m
Multiple Airlines
Mon 4/276:54 pm
GPT
-
ORD
2 stops22h 06m
Multiple Airlines
Deal found 3/30$279
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:52 pm
ORD
-
GPT
1 stop12h 08m
Multiple Airlines
Sun 4/197:20 pm
GPT
-
ORD
2 stops39h 03m
Multiple Airlines
Deal found 3/27$281
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:15 am
ORD
-
GPT
1 stop4h 09m
Delta
Sat 5/210:09 am
GPT
-
ORD
1 stop6h 33m
Delta
Deal found 3/26$291
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
-
GPT
1 stop26h 19m
Multiple Airlines
Thu 4/237:20 pm
GPT
-
ORD
2 stops49h 52m
Multiple Airlines
Deal found 3/30$303
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Tue 4/285:55 pm
GPT
-
MDW
1 stop4h 33m
Delta
Deal found 3/29$310
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:41 pm
ORD
-
GPT
1 stop5h 17m
American Airlines
Sat 5/165:03 pm
GPT
-
ORD
1 stop6h 45m
American Airlines
Deal found 3/27$310
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
-
GPT
1 stop26h 19m
Multiple Airlines
Fri 4/176:54 pm
GPT
-
ORD
2 stops26h 18m
Multiple Airlines
Deal found 3/30$311
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
-
GPT
1 stop26h 19m
Multiple Airlines
Sun 4/197:20 pm
GPT
-
ORD
2 stops15h 03m
Multiple Airlines
Deal found 3/30$315
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/125:05 am
MDW
-
GPT
1 stop13h 35m
Multiple Airlines
Thu 4/167:20 pm
GPT
-
MDW
1 stop12h 39m
Multiple Airlines
Deal found 3/28$347
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:23 am
MDW
-
GPT
1 stop6h 46m
Delta
Tue 5/121:55 pm
GPT
-
MDW
1 stop7h 14m
Delta
Deal found 3/29$365

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 March 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$246
(Kiwi.com)

One-way from

$153
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$483
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. 13% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 31, 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

Price

Cheapest round-trip

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 4/16

9:14 am-6:40 pm

1 stop9h 26m

Gulfport Biloxi Regional

Sun 4/19

7:20 pm-8:04 am

1 stop12h 44m

$291

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 4/24

5:21 pm-10:13 pm

1 stop4h 52m

Gulfport Biloxi Regional

Tue 4/28

5:55 pm-10:28 pm

1 stop4h 33m

$310

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 4/24

5:53 pm-10:13 pm

1 stop4h 20m

Gulfport Biloxi Regional

Mon 4/27

5:55 pm-11:59 pm

1 stop6h 04m

$329

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 4/17

6:41 pm-11:58 pm

1 stop5h 17m

Gulfport Biloxi Regional

Tue 4/21

5:00 am-11:21 am

1 stop6h 21m

$332
Quickest round-trip

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Mon 4/13

9:48 am-1:54 pm

1 stop4h 06m

Gulfport Biloxi Regional

Tue 4/21

5:55 pm-10:21 pm

1 stop4h 26m

$334

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 4/14

5:15 am-9:24 am

1 stop4h 09m

Gulfport Biloxi Regional

Sat 4/18

3:00 pm-8:16 pm

1 stop5h 16m

$334

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 4/25

12:43 pm-7:53 pm

1 stop7h 10m

Gulfport Biloxi Regional

Sat 5/2

2:00 pm-9:51 pm

1 stop7h 51m

$409

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Fri 4/24

5:21 pm-10:13 pm

1 stop4h 52m

Gulfport Biloxi Regional

Mon 4/27

5:55 pm-10:28 pm

1 stop4h 33m

$424

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Tue 4/21

5:48 am-2:13 pm

1 stop8h 25m

Gulfport Biloxi Regional

Sat 4/25

4:26 pm-12:45 am

1 stop8h 19m

$444

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Fri 4/10

5:59 pm-10:15 pm

1 stop4h 16m

Gulfport Biloxi Regional

Wed 4/22

2:40 pm-8:16 pm

1 stop5h 36m

$444

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 38 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 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.
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, February is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $72). 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.

How much does it cost to fly round-trip from Chicago to Gulfport?

How often are flights from Chicago to Gulfport delayed?

About 47% of weekly flights between Chicago and Gulfport have experienced delays in the past year, with the average delay time being 107 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 55% 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 March 31, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican 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
8,364 reviews

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

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
8,364 reviews
Delta
7.9
Good
8,364 reviews

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

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
9,525 reviews
Delta
7.9
Good
8,364 reviews

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

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
7.1
Good
11,543 reviews
Delta
7.9
Good
8,364 reviews

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

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, American Airlines, and United Airlines can get you from Chicago to Gulfport in just under 4h 52m. Your travel time can differ by up to 2h 18m. The distance from Chicago to Gulfport is about 789 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 32% 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, February is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $72). 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
D'Iberville

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.

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 March 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$323FlexibilityNo cancel feeOn-time71%
DeltaCheapest$253Average$410FlexibilityNo 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.