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

According to our current data, American Airlines ($248), Delta ($249), and United Airlines ($402) offers the cheapest pricing from Gulfport to Chicago. These flights start at 41% lower than the current average price 3 months from now.

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 Delta ($175), American Airlines ($175), and United Airlines ($249).

What is the cheapest day to fly from Gulfport to Chicago?

Travelers seeking maximum savings on their Gulfport to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

What is the cheapest day to fly round-trip from Gulfport to Chicago?

Sunday is generally a great day to depart. Flying on this day could help you save up to 97%.

What is the cheapest month to fly from Gulfport to Chicago?

The best pricing can be found in the month of April. Prices to Chicago from Gulfport average $426. You can even find prices in April for less than $426, as users have found deals to Chicago from as low as $253. The month of February appears to be one of the more expensive times to travel to Chicago from Gulfport. Flying in the targeted month can save you up to 57%.

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

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.

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.

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.

$175+ Flights from Gulfport to Chicago

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

Airfare is below average for this route at the moment. Gulfport to Chicago flights typically cost between $280 and $413 in August. The cheapest round-trip price found within the last 3 days was $248 on American Airlines (Aug 30-Sep 6).

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Cheap flight deals from Gulfport to Chicago

Round-trip from	$248 (American Airlines)
One-way from	$175 (Delta)
Popular in	February
Cheapest in	April
Average price	$368

From Gulfport Biloxi Regional to Chicago (CHI)

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One-way flight from Gulfport Biloxi Regional to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 15% potential increase in price ($77 potential increase over avg. RT price).

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Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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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 July 30, 2025.

Sat 8/3012:43 pmGPT - ORD

1 stop6h 25mAmerican Airlines

Sat 9/65:16 pmORD - GPT

1 stop6h 16mAmerican Airlines

Deal found 7/29

$248

Sat 8/233:45 pmGPT - MDW

1 stop5h 27mDelta

Tue 8/264:25 pmMDW - GPT

1 stop5h 13mDelta

Deal found 7/27

$249

Sat 8/305:00 pmGPT - ORD

1 stop6h 56mDelta

Wed 9/33:30 pmORD - GPT

1 stop6h 08mDelta

Deal found 7/29

$249

Sun 9/219:45 amGPT - ORD

1 stop7h 33mMultiple Airlines

Thu 9/255:46 pmORD - GPT

1 stop15h 13mMultiple Airlines

Deal found 7/30

$336

Fri 9/55:00 pmGPT - ORD

1 stop7h 15mUnited Airlines

Mon 9/89:10 pmORD - GPT

2 stops18h 55mUnited Airlines

Deal found 7/29

$402

Best flights from Gulfport to Chicago
Discover carefully curated flight deals from Gulfport to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 30, 2025.

Sat 8/3012:43 pmGPT - ORD

1 stop6h 25mAmerican Airlines

Sat 9/65:16 pmORD - GPT

1 stop6h 16mAmerican Airlines

Deal found 7/29

$248

Sat 8/233:45 pmGPT - MDW

1 stop5h 27mDelta

Tue 8/264:25 pmMDW - GPT

1 stop5h 13mDelta

Deal found 7/27

$249

Sun 9/219:45 amGPT - ORD

1 stop7h 33mMultiple Airlines

Thu 9/255:46 pmORD - GPT

1 stop15h 13mMultiple Airlines

Deal found 7/30

$336

Fri 9/55:00 pmGPT - ORD

1 stop7h 15mUnited Airlines

Mon 9/89:10 pmORD - GPT

2 stops18h 55mUnited Airlines

Deal found 7/29

$402

Sat 8/305:00 pmGPT - ORD

1 stop6h 56mDelta

Wed 9/33:30 pmORD - GPT

1 stop6h 08mDelta

Deal found 7/29

$249

Last-minute flights from Gulfport to Chicago
Discover last-minute flight deals from Gulfport to Chicago. Data last updated July 30, 2025 and is based on user searches.

Mon 8/45:25 pmGPT - ORD

1 stop6h 50mUnited Airlines

Mon 8/115:50 pmORD - GPT

2 stops19h 38mUnited Airlines

Deal found 7/28

$538

Tue 8/195:00 pmGPT - ORD

2 stops15h 05mUnited Airlines

Tue 8/267:17 amORD - GPT

2 stops12h 42mUnited Airlines

Deal found 7/29

$426

Sat 8/233:45 pmGPT - MDW

1 stop5h 27mDelta

Tue 8/264:25 pmMDW - GPT

1 stop5h 13mDelta

Deal found 7/27

$249

Thu 8/2812:55 pmGPT - ORD

1 stop9h 27mMultiple Airlines

Mon 9/16:00 amORD - GPT

1 stop10h 57mMultiple Airlines

Deal found 7/30

$461

Sat 8/3012:43 pmGPT - ORD

1 stop6h 25mAmerican Airlines

Sat 9/65:16 pmORD - GPT

1 stop6h 16mAmerican Airlines

Deal found 7/29

$248

Sat 8/305:00 pmGPT - ORD

1 stop6h 56mDelta

Wed 9/33:30 pmORD - GPT

1 stop6h 08mDelta

Deal found 7/29

$249

One-way flights from Gulfport to Chicago
Search for one-way flight options from Gulfport to Chicago. Find affordable one-way fares based on user searches. Data last updated July 30, 2025.

Mon 10/66:05 pmGPT - MDW

1 stop4h 09mDelta

Deal found 7/29

$175

Thu 10/26:34 pmGPT - ORD

1 stop5h 05mAmerican Airlines

Deal found 7/29

$175

Mon 10/66:51 pmGPT - ORD

1 stop15h 27mMultiple Airlines

Deal found 7/29

$188

Tue 8/126:09 amGPT - ORD

1 stop6h 07mDelta

Deal found 7/29

$214

Tue 8/55:25 pmGPT - ORD

1 stop5h 47mUnited Airlines

Deal found 7/29

$249

Fly from

Fly to

Route

Depart

Return

Price

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 8/30

12:43 pm-7:08 pm

1 stop6h 25m

Chicago O'Hare Intl

Sat 9/6

5:16 pm-11:32 pm

1 stop6h 16m

$248

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/23

3:45 pm-9:12 pm

1 stop5h 27m

Chicago Midway

Tue 8/26

4:25 pm-9:38 pm

1 stop5h 13m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 8/30

5:00 pm-11:56 pm

1 stop6h 56m

Chicago O'Hare Intl

Wed 9/3

3:30 pm-9:38 pm

1 stop6h 08m

$249

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sun 9/21

9:45 am-5:18 pm

1 stop7h 33m

Chicago O'Hare Intl

Thu 9/25

5:46 pm-8:59 am

1 stop15h 13m

$336

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 9/5

5:00 pm-12:15 am

1 stop7h 15m

Chicago O'Hare Intl

Mon 9/8

9:10 pm-4:05 pm

2 stops18h 55m

$402

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Mon 10/6

6:05 pm-10:14 pm

1 stop4h 09m

$175

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 10/2

6:34 pm-11:39 pm

1 stop5h 05m

$175

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Mon 10/6

6:51 pm-10:18 am

1 stop15h 27m

$188

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 8/12

6:09 am-12:16 pm

1 stop6h 07m

$214

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Tue 8/5

5:25 pm-11:12 pm

1 stop5h 47m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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, 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 $321). 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 Gulfport to Chicago?

Reviews of airlines servicing Chicago

See what other customers who have flown with Delta, United Airlines, 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

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,980 reviews

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

United Airlines

7.4

Good

8,896 reviews

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

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.
What are the cheapest airlines flying from Gulfport to Chicago round-trip?
According to our current data, American Airlines ($248), Delta ($249), and United Airlines ($402) offers the cheapest pricing from Gulfport to Chicago. These flights start at 41% lower than the current average price 3 months from now.
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 Delta ($175), American Airlines ($175), and United Airlines ($249).
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 $321). 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

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Hammond

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Porter

Valparaiso

Chesterton

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Top 2 airlines flying from Gulfport to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$116	Average$407	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$248	Average$436	FlexibilityNo cancel fee	On-time71%

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$175+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Gulfport to Chicago with Cheapflights

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2. Select your favorite providers

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Cheap flight deals from Gulfport to Chicago

Round-trip from

One-way from

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Find flight deals from Gulfport to Chicago

Cheapest flights from Gulfport to ChicagoExplore 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 July 30, 2025.

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 July 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Gulfport to Chicago that are best for you.

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.

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?

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

Reviews of airlines servicing Chicago

See what other customers who have flown with Delta, United Airlines, 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.

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?

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

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

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

How can I find direct flights from Gulfport to Chicago?

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

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

Traveling to a place near Chicago?

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Alternative routes for Gulfport to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Gulfport to Chicago

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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 July 30, 2025.