$160 Cheap Flights from Chicago (MDW) to Gulfport (GPT)

View $160 flight on Sat, Aug 30, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT)

Cheap Flights from Chicago to Gulfport (MDW-GPT)

Prices were available within the past 7 days and start at $160 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Oct 21 - Sat, Oct 25
MDW
Chicago
GPT
Gulfport
$249 Roundtrip, found 20 hours ago
$249
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Oct 21 from Chicago to Gulfport, returning Sat, Oct 25, priced at $249 found 20 hours ago
Delta
Sat, Aug 30 - Sat, Sep 13
MDW
Chicago
GPT
Gulfport
$278 Roundtrip, found 6 days ago
$278
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Aug 30 from Chicago to Gulfport, returning Sat, Sep 13, priced at $278 found 6 days ago
Delta
Fri, Aug 8 - Sat, Aug 16
MDW
Chicago
GPT
Gulfport
$284 Roundtrip, found 5 days ago
$284
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Aug 8 from Chicago to Gulfport, returning Sat, Aug 16, priced at $284 found 5 days ago
Delta
Sat, Oct 18 - Wed, Oct 22
MDW
Chicago
GPT
Gulfport
$284 Roundtrip, found 20 hours ago
$284
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Oct 18 from Chicago to Gulfport, returning Wed, Oct 22, priced at $284 found 20 hours ago
Delta
Mon, Sep 22 - Sat, Sep 27
MDW
Chicago
GPT
Gulfport
$287 Roundtrip, found 1 day ago
$287
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Sep 22 from Chicago to Gulfport, returning Sat, Sep 27, priced at $287 found 1 day ago
Delta
Tue, Aug 19 - Mon, Aug 25
MDW
Chicago
GPT
Gulfport
$289 Roundtrip, found 21 hours ago
$289
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Gulfport, returning Mon, Aug 25, priced at $289 found 21 hours ago
Delta
Wed, Sep 24 - Sat, Sep 27
MDW
Chicago
GPT
Gulfport
$292 Roundtrip, found 1 day ago
$292
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Gulfport, returning Sat, Sep 27, priced at $292 found 1 day ago
Delta
Sat, Aug 16 - Sat, Aug 23
MDW
Chicago
GPT
Gulfport
$294 Roundtrip, found 14 hours ago
$294
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Aug 16 from Chicago to Gulfport, returning Sat, Aug 23, priced at $294 found 14 hours ago
Delta
Tue, Aug 19 - Fri, Aug 22
MDW
Chicago
GPT
Gulfport
$294 Roundtrip, found 21 hours ago
$294
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Gulfport, returning Fri, Aug 22, priced at $294 found 21 hours ago
Delta
Tue, Oct 21 - Mon, Oct 27
MDW
Chicago
GPT
Gulfport
$298 Roundtrip, found 20 hours ago
$298
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Oct 21 from Chicago to Gulfport, returning Mon, Oct 27, priced at $298 found 20 hours ago

Find the cheapest month to fly from Chicago (MDW) to Gulfport (GPT)

October is typically the cheapest month to fly

From $223 - $895 per traveler.

Graph displaying average flight prices per month

Alternative airports near Gulfport

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Gulfport - Biloxi Intl. GPT. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $467
GPT
Gulfport - Biloxi Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $467
Flights from Chicago (MDW) to Gulfport (GPT)
Origin airport
Midway Intl.
Destination airport
Gulfport - Biloxi Intl.
Airlines serving
Delta
Roundtrip price
$248
Distance
789 mi

Chicago to Gulfport Flights

The cheapest times to fly from Chicago to Gulfport

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Gulfport are during the month of October. You can find some of the cheapest flights from Chicago to Gulfport with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Gulfport

Sunday is one of the best days to book for cheap flights from Chicago to Gulfport: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Gulfport

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Gulfport in 2025. You can also book with separate airlines for your outbound and return journeys, from $160 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Gulfport flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Gulfport airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT) cost?
Discover the latest flight deals from MDW to GPT by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to GPT?
The cheapest flights from MDW to GPT are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to GPT?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to GPT. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT)?
Direct flights from Midway Intl. Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to GPT?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change based on a number of factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT)?
Choose a flight from Midway Intl. Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT) last-minute?
Waiting until just before your departure to book a flight from MDW to GPT often results in higher prices. While you may find some last-minute offers, they aren't always guaranteed. Be flexible with your itinerary for a better chance of getting a bargain.
Is it cheaper to book a MDW to GPT flight and hotel package?
You can save money by securing a MDW to GPT flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've chosen your ideal flights and accommodations, consider other add-ons like car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Gulfport - Biloxi Intl. Airport (GPT)?
Usually, it's possible to reschedule or cancel your MDW to GPT flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.