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$142+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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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 May 10, 2026.

This American Airlines deal was found by Cheapflights users on 5/7. 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 6/96:38 pm
GPT
-
ORD
1 stop5h 20m
American Airlines
Tue 6/165:34 pm
ORD
-
GPT
1 stop6h 25m
American Airlines
Deal found 5/7$291
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Sat 6/66:38 pm
GPT
-
ORD
1 stop5h 20m
American Airlines
Mon 6/85:34 pm
ORD
-
GPT
1 stop6h 25m
American Airlines
Deal found 5/6$300
This Delta deal was found by Cheapflights users on 5/8. 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 7/296:00 pm
GPT
-
MDW
1 stop4h 15m
Delta
Mon 8/36:05 am
MDW
-
GPT
1 stop6h 58m
Delta
Deal found 5/8$305
This American Airlines deal was found by Cheapflights users on 5/9. 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.
Sat 6/276:38 pm
GPT
-
ORD
1 stop5h 20m
American Airlines
Sun 6/285:00 am
ORD
-
GPT
1 stop5h 52m
American Airlines
Deal found 5/9$305
This Delta deal was found by Cheapflights users on 5/8. 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 8/2710:01 am
GPT
-
MDW
1 stop6h 14m
Delta
Sun 8/306:05 am
MDW
-
GPT
1 stop6h 58m
Delta
Deal found 5/8$319
This Delta deal was found by Cheapflights users on 5/8. 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 7/296:00 pm
GPT
-
ORD
1 stop5h 53m
Delta
Mon 8/36:40 am
ORD
-
GPT
1 stop6h 23m
Delta
Deal found 5/8$339
This Delta deal was found by Cheapflights users on 5/8. 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 8/276:01 pm
GPT
-
ORD
1 stop5h 57m
Delta
Sun 8/306:40 am
ORD
-
GPT
1 stop6h 23m
Delta
Deal found 5/8$344
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 8/105:31 pm
GPT
-
ORD
2 stops38h 22m
Multiple Airlines
Sat 8/155:13 pm
ORD
-
GPT
1 stop25h 57m
Multiple Airlines
Deal found 5/8$360
This American Airlines deal was found by Cheapflights users on 5/10. 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 5/196:18 am
GPT
-
ORD
1 stop8h 07m
American Airlines
Tue 5/265:00 am
ORD
-
GPT
1 stop5h 52m
American Airlines
Deal found 5/10$365
This Delta deal was found by Cheapflights users on 5/10. 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 5/186:02 pm
GPT
-
ORD
1 stop5h 57m
Delta
Thu 5/288:10 am
ORD
-
GPT
1 stop4h 59m
Delta
Deal found 5/10$369
This Delta deal was found by Cheapflights users on 5/5. 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 5/211:55 pm
GPT
-
MDW
1 stop7h 14m
Delta
Tue 5/265:12 pm
MDW
-
GPT
1 stop4h 39m
Delta
Deal found 5/5$379
This Delta deal was found by Cheapflights users on 5/5. 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 5/211:55 pm
GPT
-
ORD
1 stop6h 31m
Delta
Tue 5/262:59 pm
ORD
-
GPT
1 stop6h 52m
Delta
Deal found 5/5$379

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(American Airlines)

One-way from

$142
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$323
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. 22% potential increase in price ($118 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 18% potential price decrease ($64 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 10, 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

Price

Cheapest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 8/27

10:01 am-4:15 pm

1 stop6h 14m

Chicago Midway

Sun 8/30

6:05 am-1:03 pm

1 stop6h 58m

$319

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 7/29

6:00 pm-11:53 pm

1 stop5h 53m

Chicago O'Hare Intl

Mon 8/3

6:40 am-1:03 pm

1 stop6h 23m

$339

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 5/21

1:55 pm-8:26 pm

1 stop6h 31m

Chicago O'Hare Intl

Tue 5/26

2:59 pm-9:51 pm

1 stop6h 52m

$379

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 6/24

10:39 am-5:42 pm

1 stop7h 03m

Chicago O'Hare Intl

Mon 6/29

5:59 am-10:52 am

1 stop4h 53m

$417

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 7/8

6:00 pm-11:53 pm

1 stop5h 53m

Chicago O'Hare Intl

Mon 7/13

8:03 am-1:05 pm

1 stop5h 02m

$419

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 7/15

6:00 pm-10:15 pm

1 stop4h 15m

Chicago Midway

Mon 7/20

5:10 pm-10:14 pm

1 stop5h 04m

$424

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Mon 8/10

6:01 pm-10:36 pm

1 stop4h 35m

Chicago Midway

Sat 8/15

4:39 pm-8:53 pm

1 stop4h 14m

$434

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 10/27

5:15 pm-10:36 pm

1 stop5h 21m

Chicago O'Hare Intl

Sat 10/31

9:25 am-4:02 pm

1 stop6h 37m

$468

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 10/9

6:00 pm-11:50 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 10/12

5:30 am-9:39 am

1 stop4h 09m

$488

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 5/21

7:04 am-2:20 pm

1 stop7h 16m

Chicago O'Hare Intl

Sun 5/24

5:10 am-10:14 am

1 stop5h 04m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 33 resultsSorted by cheapest first
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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 May.
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 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.
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

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

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 May 10, 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.
American Airlines
7.1
Good
11,667 reviews

Boarding

7.5

Crew

7.9

Overall

7.1

Food

6.4

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,667 reviews
American Airlines
7.1
Good
11,667 reviews

Boarding

7.5

Crew

7.9

Overall

7.1

Food

6.4

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 5h 21m. Delta provides one of the quickest options available for as low as $468. 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 ($319) offers the cheapest pricing from Gulfport to Chicago. These flights start at 37% 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.

See more FAQs

Traveling to a place near Chicago?

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

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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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$436FlexibilityNo cancel feeOn-time71%
DeltaCheapest$319Average$553FlexibilityNo cancel feeOn-timeN/A

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