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

Flying on Delta is currently your cheapest option to Gulfport, with prices starting at $249. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $250 and $391, respectively. You may be able to fly from Chicago to Gulfport for 41% less than the average price by searching for these airlines.

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

For one-way options, check prices for Delta. According to our data, you can fly for as low as $159. Users have also found prices from $190 and $270 on American Airlines and United Airlines, respectively.

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

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

In terms of precipitation, rainfall in Gulfport ranges from 3.6 - 7.2 inches per month. July is typically the wettest month, when rainfall can reach 7.2 in. October is typically the driest time to visit Gulfport when rainfall is around 3.6 in.

If weather is an important factor for your trip to Gulfport, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

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

Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 47% on your flight compared to booking on days when demand is much higher.

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

August can be a great time to fly to Gulfport from Chicago with a flight ticket averaging about $423. Cheapflights users have found deals in the month of August for as cheap as $248. The most expensive prices can be found in the month of February.

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

A simple way to save on the total cost of your ticket is to fly from Chicago to Gulfport in the morning. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight at noon.

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.

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.

$159+ Flights from Chicago to Gulfport

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Cheap flight deals from Chicago to Gulfport

Round-trip from	$249 (Delta)
One-way from	$159 (Delta)
Popular in	February
Cheapest in	August
Average price	$548

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. 12% potential increase in price ($61 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($14 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 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 July 3, 2025.

Sat 8/164:25 pmMDW - GPT

1 stop5h 13mDelta

Sat 8/2311:30 amGPT - MDW

1 stop3h 58mDelta

Deal found 7/2

$249

Sat 8/163:30 pmORD - GPT

1 stop6h 08mDelta

Sat 8/233:45 pmGPT - ORD

1 stop5h 51mDelta

Deal found 7/2

$249

Thu 8/146:25 pmORD - GPT

1 stop5h 34mAmerican Airlines

Thu 8/216:30 pmGPT - ORD

1 stop5h 18mAmerican Airlines

Deal found 7/2

$250

Fri 10/316:00 amORD - GPT

1 stop7h 20mUnited Airlines

Sun 11/25:15 pmGPT - ORD

1 stop7h 00mUnited Airlines

Deal found 7/2

$388

Thu 7/175:05 amORD - GPT

3 stops26h 40mMultiple Airlines

Sun 7/2012:55 pmGPT - ORD

2 stops18h 09mMultiple Airlines

Deal found 7/1

$493

Best flights from Chicago to Gulfport
Discover carefully curated flight deals from Chicago to Gulfport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2025.

Sat 8/164:25 pmMDW - GPT

1 stop5h 13mDelta

Sat 8/2311:30 amGPT - MDW

1 stop3h 58mDelta

Deal found 7/2

$249

Thu 8/146:25 pmORD - GPT

1 stop5h 34mAmerican Airlines

Thu 8/216:30 pmGPT - ORD

1 stop5h 18mAmerican Airlines

Deal found 7/2

$250

Thu 9/186:10 amORD - GPT

2 stops12h 18mMultiple Airlines

Sun 9/2110:33 amGPT - ORD

1 stop6h 45mMultiple Airlines

Deal found 7/3

$340

Sat 8/237:00 amORD - GPT

1 stop6h 27mUnited Airlines

Sun 8/315:00 pmGPT - ORD

2 stops13h 15mUnited Airlines

Deal found 7/3

$391

Sat 8/163:30 pmORD - GPT

1 stop6h 08mDelta

Sat 8/236:09 amGPT - ORD

1 stop6h 08mDelta

Deal found 7/2

$249

Last-minute flights from Chicago to Gulfport
Discover last-minute flight deals from Chicago to Gulfport. Data last updated July 3, 2025 and is based on user searches.

Wed 7/97:05 amORD - GPT

1 stop5h 12mAmerican Airlines

Tue 7/156:36 pmGPT - ORD

1 stop5h 21mAmerican Airlines

Deal found 7/1

$284

Wed 7/910:35 amORD - GPT

1 stop5h 39mUnited Airlines

Tue 7/155:25 pmGPT - ORD

2 stops14h 40mUnited Airlines

Deal found 7/1

$461

Thu 7/1011:20 amORD - GPT

1 stop5h 55mDelta

Sat 7/126:07 amGPT - ORD

1 stop6h 26mDelta

Deal found 7/2

$309

Fri 7/114:22 pmMDW - GPT

1 stop5h 41mDelta

Sat 7/123:30 pmGPT - MDW

1 stop6h 12mDelta

Deal found 7/2

$309

Thu 7/175:05 amORD - GPT

3 stops26h 40mMultiple Airlines

Sun 7/2012:55 pmGPT - ORD

2 stops18h 09mMultiple Airlines

Deal found 7/1

$493

Thu 8/146:25 pmORD - GPT

1 stop5h 34mAmerican Airlines

Thu 8/216:30 pmGPT - ORD

1 stop5h 18mAmerican Airlines

Deal found 7/2

$250

Sat 8/164:25 pmMDW - GPT

1 stop5h 13mDelta

Sat 8/2311:30 amGPT - MDW

1 stop3h 58mDelta

Deal found 7/2

$249

Sat 8/163:30 pmORD - GPT

1 stop6h 08mDelta

Sat 8/233:45 pmGPT - ORD

1 stop5h 51mDelta

Deal found 7/2

$249

Sat 8/162:10 pmORD - GPT

2 stops23h 18mUnited Airlines

Sat 8/235:00 pmGPT - ORD

1 stop5h 41mUnited Airlines

Deal found 7/2

$393

One-way flights from Chicago to Gulfport
Search for one-way flight options from Chicago to Gulfport. Find affordable one-way fares based on user searches. Data last updated July 3, 2025.

Sat 8/164:25 pmMDW - GPT

1 stop5h 13mDelta

Deal found 7/2

$159

Sat 8/163:30 pmORD - GPT

1 stop6h 08mDelta

Deal found 7/2

$159

Thu 8/284:21 pmORD - GPT

1 stop6h 36mAmerican Airlines

Deal found 7/1

$190

Sun 8/103:18 pmORD - GPT

2 stops16h 27mMultiple Airlines

Deal found 7/2

$236

Sat 8/168:50 amORD - GPT

2 stops12h 54mUnited Airlines

Deal found 7/2

$270

Cheapflights Fare Finder

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

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 8/16

4:25 pm-9:38 pm

1 stop5h 13m

Gulfport Biloxi Regional

Sat 8/23

11:30 am-3:28 pm

1 stop3h 58m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

3:30 pm-9:38 pm

1 stop6h 08m

Gulfport Biloxi Regional

Sat 8/23

3:45 pm-9:36 pm

1 stop5h 51m

$249

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 8/14

6:25 pm-11:59 pm

1 stop5h 34m

Gulfport Biloxi Regional

Thu 8/21

6:30 pm-11:48 pm

1 stop5h 18m

$250

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

2:10 pm-1:28 pm

2 stops23h 18m

Gulfport Biloxi Regional

Sat 8/23

5:00 pm-10:41 pm

1 stop5h 41m

$393

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 7/17

5:05 am-7:45 am

3 stops26h 40m

Gulfport Biloxi Regional

Sun 7/20

12:55 pm-7:04 am

2 stops18h 09m

$493

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 8/16

4:25 pm-9:38 pm

1 stop5h 13m

$159

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

3:30 pm-9:38 pm

1 stop6h 08m

$159

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Thu 8/28

4:21 pm-10:57 pm

1 stop6h 36m

$190

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sun 8/10

3:18 pm-7:45 am

2 stops16h 27m

$236

ChicagoGulfport

ORD - GPT

ORDGPT

Chicago O'Hare Intl

Sat 8/16

8:50 am-9:44 pm

2 stops12h 54m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $420). 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?

Reviews of airlines servicing Gulfport

Peruse reviews from past customers who have flown with Delta, United Airlines, and American 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

8.0

Very good

7,970 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

7,970 reviews

Delta

8.0

Very good

7,970 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

8,845 reviews

Delta

8.0

Very good

7,970 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

7,970 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 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.
What are the cheapest airlines flying from Chicago to Gulfport round-trip?
Flying on Delta is currently your cheapest option to Gulfport, with prices starting at $249. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $250 and $391, respectively. You may be able to fly from Chicago to Gulfport for 41% less than the average price by searching for these airlines.
What are the cheapest airlines to fly from Chicago to Gulfport one-way?
For one-way options, check prices for Delta. According to our data, you can fly for as low as $159. Users have also found prices from $190 and $270 on American Airlines and United Airlines, respectively.
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, November is the cheapest month in which you can book a flight from Chicago to Gulfport (average of $318). Flying from Chicago to Gulfport in March is currently the most expensive (average of $420). 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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Other flights to Gulfport

Top 2 airlines flying from Chicago to Gulfport

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$248	Average$364	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$253	Average$427	FlexibilityNo cancel fee	On-timeN/A

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$159+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Gulfport with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Gulfport

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Chicago to Gulfport

Cheapest flights from Chicago to GulfportExplore 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 July 3, 2025.

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 July 3, 2025.

Cheapflights Fare Finder

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

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.

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?

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

Reviews of airlines servicing Gulfport

Peruse reviews from past customers who have flown with Delta, United Airlines, and American 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.

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?

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

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

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

How can I find direct flights from Chicago to Gulfport?

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

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

Traveling to a place near Chicago?

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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Gulfport

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

Top 2 airlines flying from Chicago to Gulfport

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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 July 3, 2025.