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$158+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
GPT — CHI
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
1 adult, Economy
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Cheap 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 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$376
(Delta)

One-way from

$158
(American Airlines)

Popular in

May

Cheapest in

January

Average price

$446
Provider with most accurate pricing for Gulfport Biloxi Regional-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Chicago (CHI) flights.
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From Gulfport Biloxi Regional to Chicago (CHI)
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One-way flight from Gulfport Biloxi Regional to Chicago (CHI)
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High demand for flights, 5% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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Find 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 20, 2024.

This American Airlines deal was found by Cheapflights users on 12/18. 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 12/2612:55 pmGPT - ORD
1 stop6h 29mAmerican Airlines
Tue 12/313:23 pmORD - GPT
1 stop5h 41mAmerican Airlines
Deal found 12/18$572
This Delta deal was found by Cheapflights users on 12/19. 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 12/302:51 pmGPT - MDW
1 stop7h 15mDelta
Fri 1/312:10 pmMDW - GPT
1 stop4h 20mDelta
Deal found 12/19$804
This Delta deal was found by Cheapflights users on 12/19. 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 12/2011:13 amGPT - ORD
1 stop4h 59mDelta
Mon 12/235:40 amORD - GPT
1 stop4h 53mDelta
Deal found 12/19$818
This United Airlines deal was found by Cheapflights users on 12/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/197:06 amGPT - ORD
2 stops9h 47mUnited Airlines
Thu 12/2610:55 amORD - GPT
2 stops8h 52mUnited Airlines
Deal found 12/18$1,276

Find flights from Gulfport to Chicago within your budget

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 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Tue 1/21

6:05 am-10:12 am

1 stop4h 07m

Chicago Midway

Sat 1/25

3:41 pm-8:52 pm

1 stop5h 11m

$376

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 1/21

5:07 am-11:12 am

1 stop6h 05m

Chicago O'Hare Intl

Sat 1/25

12:25 pm-6:15 pm

1 stop5h 50m

$376

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 1/21

4:55 pm-10:45 pm

1 stop5h 50m

Chicago O'Hare Intl

Sat 1/25

7:30 am-7:46 pm

2 stops12h 16m

$437

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 1/7

6:22 am-2:15 pm

1 stop7h 53m

$158

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 12/30

6:20 pm-7:47 am

1 stop13h 27m

$184

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 1/13

2:01 pm-7:42 am

2 stops17h 41m

$252

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Tue 12/24

5:30 pm-10:06 pm

1 stop4h 36m

$299

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 12/28

5:01 am-3:35 pm

3 stops34h 34m

$1,308

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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.

Travel insights for flights from Gulfport to Chicago

Get recent, data-driven insights about flights from Gulfport to Chicago including ideal travel times, pricing trends, and more.

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

Currently, August is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $245). Flying from Gulfport to Chicago in March is currently the most expensive (average of $317). 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.

What is the cheapest time of day to fly from GPT to CHI?

Find hourly flight availability from Gulfport to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 20, 2024.

Unlike in the morning, when flights are generally more expensive, you can save up to 31% on flights from Gulfport to Chicago by exploring options for tickets in the evening.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 20, 2024.
Read through reviews of airlines operating flights from Gulfport to Chicago, such as American Airlines and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,545 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Alaska Airlines
8.0
Very good
9,545 reviews
Alaska Airlines
8.0
Very good
9,545 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Delta
8.0
Very good
8,601 reviews
Alaska Airlines
8.0
Very good
9,545 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

United Airlines
7.4
Good
9,043 reviews
Alaska Airlines
8.0
Very good
9,545 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,545 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

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. 3 airlines have flights to Chicago from Gulfport Biloxi Regional on a regular basis.

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

    According to our current data, Delta ($376), American Airlines ($376), and United Airlines ($437) offers the cheapest pricing from Gulfport to Chicago.

  • What are the cheapest airlines to fly from Gulfport to Chicago one-way?

    The cheapest airlines for a one-way flight from Gulfport to Chicago are American Airlines ($158), United Airlines ($252), and Delta ($433).

  • 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, August is the cheapest month in which you can book a flight from Gulfport to Chicago (average of $245). Flying from Gulfport to Chicago in March is currently the most expensive (average of $317). 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.

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Alternative routes for Gulfport to Chicago

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Top 3 airlines flying from Gulfport to Chicago

Discover the top 3 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 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$158Average$382FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$224Average$391FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$317FlexibilityNo cancel feeOn-time69%
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