What is the cheapest airline to fly from Chicago Midway Airport to Gulfport round-trip?

Delta, at $249, was found to be the cheapest airline from Chicago Midway Airport to Gulfport..

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

Travelers seeking maximum savings on their Chicago Midway Airport to Gulfport flight should consider departing on Thursday mornings when fares are most often at their lowest. Thursday mornings 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 Midway Airport to Gulfport?

Flying to your destination on a Thursday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Gulfport. Check prices with Cheapflights to find a great deal for your trip.

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

The best pricing can be found in the month of August. Prices to Gulfport from Chicago Midway Airport average $424. You can even find prices in August for less than $424, as users have found deals to Gulfport from as low as $248. The month of February appears to be one of the more expensive times to travel to Gulfport from Chicago Midway Airport. Flying in the targeted month can save you up to 35%.

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

When flying from Chicago Midway Airport to Gulfport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 31% versus a flight at noon.

What airport do you fly into for flights to Gulfport from Chicago Midway?

Most people fly into Gulfport Biloxi Regional (GPT) if they book a flight to Gulfport from Chicago Midway. On average, Biloxi Regional has 0 inbound flights from Chicago Midway per day from 1 airline. Gulfport Biloxi Regional is conveniently located just 3.1 mi from Gulfport’s city center.

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

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

How can I find direct flights from Midway to Gulfport?

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

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

Yes. Cheapflights offers flight deals from Midway 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.

$169+ Flights from Chicago Midway Airport to Gulfport

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Cheap flight deals from Midway to Gulfport

Round-trip from	$249 (Delta)
One-way from	$169 (Delta)
Popular in	February
Cheapest in	August
Average price	$562

From Chicago Midway to Gulfport Biloxi Regional

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One-way flight from Chicago Midway to Gulfport Biloxi Regional

Search Deals

Highest demand for flights based on searches. 12% potential increase in price ($60 potential increase over avg. RT price).

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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 Midway to Gulfport

Cheapest flights from Midway to Gulfport
Explore the most affordable flight options available from Midway to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

Wed 8/274:25 pmMDW - GPT

1 stop5h 13mDelta

Wed 9/35:00 pmGPT - MDW

1 stop4h 26mDelta

Deal found 7/28

$249

Best flights from Midway to Gulfport
Discover carefully curated flight deals from Midway to Gulfport that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2025.

Wed 8/274:25 pmMDW - GPT

1 stop5h 13mDelta

Wed 9/35:00 pmGPT - MDW

1 stop4h 26mDelta

Deal found 7/28

$249

Last-minute flights from Midway to Gulfport
Discover last-minute flight deals from Midway to Gulfport. Data last updated July 29, 2025 and is based on user searches.

Fri 8/84:22 pmMDW - GPT

1 stop5h 41mDelta

Sun 8/106:07 amGPT - MDW

1 stop5h 41mDelta

Deal found 7/29

$419

Wed 8/274:25 pmMDW - GPT

1 stop5h 13mDelta

Wed 9/35:00 pmGPT - MDW

1 stop4h 26mDelta

Deal found 7/28

$249

One-way flights from Midway to Gulfport
Search for one-way flight options from Midway to Gulfport. Find affordable one-way fares based on user searches. Data last updated July 29, 2025.

Sat 8/234:25 pmMDW - GPT

1 stop5h 13mDelta

Deal found 7/27

$169

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Wed 8/27

4:25 pm-9:38 pm

1 stop5h 13m

Gulfport Biloxi Regional

Wed 9/3

5:00 pm-9:26 pm

1 stop4h 26m

$249

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 8/23

4:25 pm-9:38 pm

1 stop5h 13m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Best time to book a flight from Midway to Gulfport

Have a flexible travel schedule? Discover the best time to fly to Gulfport from Midway 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 Midway Airport to Gulfport

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Gulfport (average of $318). Flying from Chicago Midway Airport to Gulfport in March is currently the most expensive (average of $417). 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 Gulfport

Read through reviews of airlines operating flights from Chicago Midway Airport to Gulfport, such as Delta. 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

7,979 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

7,979 reviews

Delta

8.0

Very good

7,979 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 Midway?
Most people fly into Gulfport Biloxi Regional (GPT) if they book a flight to Gulfport from Chicago Midway. On average, Biloxi Regional has 0 inbound flights from Chicago Midway per day from 1 airline. Gulfport Biloxi Regional is conveniently located just 3.1 mi from Gulfport’s city center.
What is the cheapest airline to fly from Chicago Midway Airport to Gulfport round-trip?
Delta, at $249, was found to be the cheapest airline from Chicago Midway Airport to Gulfport..
Can I find deals for flights from Midway to Gulfport that include hotel bookings?
Yes. In addition to deals on Midway to Gulfport flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to Gulfport?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Gulfport.
Can I find deals for business class flights from Midway to Gulfport?
Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Gulfport?
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Gulfport (average of $318). Flying from Chicago Midway Airport to Gulfport in March is currently the most expensive (average of $417). 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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Other flights to Gulfport

Top airline flying from Midway to Gulfport

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$253	Average$436	FlexibilityNo cancel fee	On-timeN/A

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$169+ Cheap flights from Midway (MDW) 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Gulfport with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Gulfport

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Midway to Gulfport

Cheapest flights from Midway to GulfportExplore the most affordable flight options available from Midway to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

Explore the most affordable flight options available from Midway to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Midway to Gulfport

Have a flexible travel schedule? Discover the best time to fly to Gulfport from Midway with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Gulfport

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

Reviews of airlines servicing Gulfport

Read through reviews of airlines operating flights from Chicago Midway Airport to Gulfport, such as Delta. 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 Midway 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 Midway?

What is the cheapest airline to fly from Chicago Midway Airport to Gulfport round-trip?

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

How can I find direct flights from Midway to Gulfport?

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

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

Traveling to a place near Gulfport?

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 Midway to Gulfport

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

Top airline flying from Midway to Gulfport

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Book with Flexibility

Travel Smart

Cheapest flights from Midway to Gulfport
Explore the most affordable flight options available from Midway to Gulfport. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.