HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$134+ Cheap flights from Gulfport (GPT) to Chicago (CHI)

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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 Gulfport to Chicago

Cheapest flights from Gulfport to Chicago
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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:35 pmGPT - ORD
1 stop6h 47mAmerican Airlines
Thu 1/12:50 pmORD - GPT
1 stop8h 07mAmerican Airlines
Deal found 12/17$309
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:13 pmGPT - ORD
1 stop5h 22mAmerican Airlines
Sat 1/176:55 pmORD - GPT
1 stop5h 04mAmerican Airlines
Deal found 12/16$319
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:58 pmGPT - ORD
1 stop5h 17mAmerican Airlines
Thu 1/16:37 pmORD - GPT
1 stop5h 35mAmerican Airlines
Deal found 12/16$339
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:15 pmGPT - ORD
1 stop5h 22mUnited Airlines
Tue 12/302:17 pmORD - GPT
1 stop7h 20mUnited Airlines
Deal found 12/17$367
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:05 amGPT - ORD
1 stop7h 07mAmerican Airlines
Sat 12/276:38 pmORD - GPT
1 stop5h 34mAmerican Airlines
Deal found 12/16$424
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/2310:05 amGPT - ORD
2 stops14h 25mMultiple Airlines
Thu 1/112:09 pmORD - GPT
1 stop7h 01mMultiple Airlines
Deal found 12/16$437
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/245:21 pmGPT - ORD
1 stop6h 41mDelta
Sat 12/276:45 amORD - GPT
1 stop6h 41mDelta
Deal found 12/17$448
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/255:21 pmGPT - MDW
1 stop5h 01mDelta
Thu 1/19:50 amMDW - GPT
1 stop5h 55mDelta
Deal found 12/17$468
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:15 pmGPT - ORD
1 stop6h 59mUnited Airlines
Sat 1/312:45 pmORD - GPT
2 stops24h 37mUnited Airlines
Deal found 12/17$613
This Delta deal was found by Cheapflights users on 12/16. 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.
Tue 12/235:21 pmGPT - MDW
1 stop5h 01mDelta
Thu 1/19:50 amMDW - GPT
1 stop5h 55mDelta
Deal found 12/16$619

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Delta)

One-way from

$134
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$758
Provider with most accurate pricing for Gulfport Biloxi Regional-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Chicago (CHI) flights.
Search Deals
From Gulfport Biloxi Regional to Chicago (CHI)
Search Deals
One-way flight from Gulfport Biloxi Regional to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Gulfport to Chicago that are best for you.

Fly from

Gulfport

Fly to

Chicago

Route

Depart

Return

Price

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 1/9

10:21 am-4:44 pm

1 stop6h 23m

Chicago O'Hare Intl

Tue 1/13

2:50 pm-9:53 pm

1 stop7h 03m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 1/6

1:03 pm-8:39 pm

1 stop7h 36m

Chicago O'Hare Intl

Sat 1/17

5:37 pm-11:59 pm

1 stop6h 22m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 1/9

10:21 am-4:44 pm

1 stop6h 23m

Chicago O'Hare Intl

Wed 1/14

9:55 am-3:09 pm

1 stop5h 14m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 1/8

6:05 am-10:59 am

1 stop4h 54m

Chicago O'Hare Intl

Wed 1/14

9:55 am-3:09 pm

1 stop5h 14m

$269

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 1/7

6:05 am-10:59 am

1 stop4h 54m

Chicago O'Hare Intl

Tue 1/13

2:50 pm-9:53 pm

1 stop7h 03m

$294

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 3/13

10:04 am-4:46 pm

1 stop6h 42m

Chicago O'Hare Intl

Sun 3/15

7:05 am-1:59 pm

1 stop6h 54m

$294

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 1/10

10:21 am-4:44 pm

1 stop6h 23m

Chicago O'Hare Intl

Wed 1/14

2:50 pm-9:53 pm

1 stop7h 03m

$294

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 1/10

10:21 am-4:44 pm

1 stop6h 23m

Chicago O'Hare Intl

Sat 1/17

8:00 am-3:09 pm

1 stop7h 09m

$294

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 3/12

2:44 pm-9:00 pm

1 stop6h 16m

Chicago O'Hare Intl

Sun 3/15

7:05 am-1:59 pm

1 stop6h 54m

$294

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 1/8

6:05 am-10:59 am

1 stop4h 54m

Chicago O'Hare Intl

Tue 1/13

6:00 am-9:53 pm

2 stops15h 53m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 29 results
1
2
3

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Gulfport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Gulfport-Chicago flight deals on Cheapflights vs. eDreams >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 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 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.
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

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

Currently, February is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $57). Flying from Gulfport to Chicago in January is currently the most expensive (average of $174). 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 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 December 18, 2025.
See what other customers who have flown with Delta and 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.
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

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
8,005 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

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
11,054 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

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 Gulfport to Chicago. 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 from for flights from Gulfport to Chicago?

    For a flight from Gulfport to Chicago, you will be flying from Biloxi Regional. Gulfport Biloxi Regional (GPT) is just 3.1 mi from the center of the city. Biloxi Regional is the only Gulfport airport and it handles 0 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Gulfport Biloxi Regional on a regular basis.

  • How long is the flight from Gulfport to Chicago?

    A quick flight from Gulfport to Chicago can take about 6h 23m. Delta provides one of the quickest options available for as low as $269. There are 802 mi between Gulfport and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    According to our current data, American Airlines ($248), and Delta ($327) offers the cheapest pricing from Gulfport to Chicago. These flights start at 38% lower than the current average price 3 months from now.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Gulfport to Chicago 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 Gulfport to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $57). Flying from Gulfport to Chicago in January is currently the most expensive (average of $174). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 Gulfport to Chicago

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

Top 2 airlines flying from Gulfport to Chicago

Discover the top 2 airlines 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 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$436FlexibilityNo cancel feeOn-time71%
DeltaCheapest$327Average$553FlexibilityNo 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.