$150 Cheap Flights from Chicago (ORD) to Gulfport (GPT)

View $150 flight on Sun, Jan 25, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT)

Cheap Flights from Chicago to Gulfport (ORD-GPT)

Prices were available within the past 7 days and start at $150 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Jan 26 - Tue, Feb 3
ORD
Chicago
GPT
Gulfport
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Mon, Jan 26 from Chicago to Gulfport, returning Tue, Feb 3, priced at $249 just found
Delta
Mon, Jan 26 - Tue, Feb 3
ORD
Chicago
GPT
Gulfport
$249 Roundtrip, just found
$249
Roundtrip
just found
Select Delta flight, departing Mon, Jan 26 from Chicago to Gulfport, returning Tue, Feb 3, priced at $249 just found
American Airlines
Mon, Jan 26 - Tue, Feb 3
ORD
Chicago
GPT
Gulfport
$254 Roundtrip, just found
$254
Roundtrip
just found
Select American Airlines flight, departing Mon, Jan 26 from Chicago to Gulfport, returning Tue, Feb 3, priced at $254 just found
American Airlines
Sat, Nov 8 - Sat, Nov 15
ORD
Chicago
GPT
Gulfport
$259 Roundtrip, found 3 days ago
$259
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Nov 8 from Chicago to Gulfport, returning Sat, Nov 15, priced at $259 found 3 days ago
American Airlines
Wed, Nov 12 - Sat, Nov 15
ORD
Chicago
GPT
Gulfport
$264 Roundtrip, found 3 days ago
$264
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Nov 12 from Chicago to Gulfport, returning Sat, Nov 15, priced at $264 found 3 days ago
United
Thu, Nov 20 - Mon, Nov 24
ORD
Chicago
GPT
Gulfport
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
Select United flight, departing Thu, Nov 20 from Chicago to Gulfport, returning Mon, Nov 24, priced at $270 found 1 day ago
United
Fri, Nov 14 - Mon, Nov 17
ORD
Chicago
GPT
Gulfport
$271 Roundtrip, found 2 days ago
$271
Roundtrip
found 2 days ago
Select United flight, departing Fri, Nov 14 from Chicago to Gulfport, returning Mon, Nov 17, priced at $271 found 2 days ago
United
Tue, Jan 20 - Tue, Jan 27
ORD
Chicago
GPT
Gulfport
$274 Roundtrip, found 17 hours ago
$274
Roundtrip
found 17 hours ago
Select United flight, departing Tue, Jan 20 from Chicago to Gulfport, returning Tue, Jan 27, priced at $274 found 17 hours ago
United
Tue, Jan 27 - Tue, Feb 3
ORD
Chicago
GPT
Gulfport
$275 Roundtrip, found 3 days ago
$275
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jan 27 from Chicago to Gulfport, returning Tue, Feb 3, priced at $275 found 3 days ago
United
Thu, Dec 11 - Wed, Dec 17
ORD
Chicago
GPT
Gulfport
$276 Roundtrip, found 6 days ago
$276
Roundtrip
found 6 days ago
Select United flight, departing Thu, Dec 11 from Chicago to Gulfport, returning Wed, Dec 17, priced at $276 found 6 days ago

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

July is typically the cheapest month to fly

From $223 - $485 per traveler.

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 $289
GPT
Gulfport - Biloxi Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $289

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT) cost?
Grab a cheap one-way flight from $150 or cheap return flight from $249 from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT)?
Planning your trip for January may help you find better deals, as it's the cheapest month for flights between ORD and GPT. You'll typically find the lowest fares during off-peak months.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT)?
To find the cheapest airline flying from ORD to GPT, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT)?
There aren't any daily nonstop flights available from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from ORD to GPT?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT)?
To avoid potential delays on the O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT) route, travel before 3 PM. Departures after this time have a 22% higher chance of cancellation.**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 O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT) last-minute?
Holding off until just before your departure to book your flight from ORD to GPT often results in higher prices. While you may find some last-minute offers, they're not always guaranteed. Keep your travel plans flexible for a better chance of snagging a bargain.
Is it cheaper to book an ORD to GPT flight and hotel package?
Booking an ORD to GPT flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Choose from our impressive range of hotels and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Gulfport - Biloxi Intl. Airport (GPT)?
In most instances, you're able to reschedule or cancel your ORD to GPT flight. However, additional fees may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you want more details, head to our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Gulfport - Biloxi Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$248
Distance
801 mi

Book with confidence

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 January. 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 $150 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.

 

Chicago to Gulfport Flights

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*Available to One Key members.