$100 Cheap Flights from Gulfport (GPT) to Chicago (ORD)

View $100 flight on Wed, May 28, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Gulfport to Chicago (GPT-ORD)

Prices were available within the past 7 days and start at $100 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, May 28 - Fri, May 30
GPT
Gulfport
ORD
Chicago
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, May 28 from Gulfport to Chicago, returning Fri, May 30, priced at $199 found 1 hour ago
Delta
Sat, May 24 - Wed, May 28
GPT
Gulfport
ORD
Chicago
$202 Roundtrip, found 3 hours ago
$202
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, May 24 from Gulfport to Chicago, returning Wed, May 28, priced at $202 found 3 hours ago
Delta
Wed, May 28 - Tue, Jun 3
GPT
Gulfport
ORD
Chicago
$224 Roundtrip, found 1 hour ago
$224
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, May 28 from Gulfport to Chicago, returning Tue, Jun 3, priced at $224 found 1 hour ago
American Airlines
Sat, Jul 5 - Sat, Jul 12
GPT
Gulfport
ORD
Chicago
$224 Roundtrip, found 6 hours ago
$224
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Jul 5 from Gulfport to Chicago, returning Sat, Jul 12, priced at $224 found 6 hours ago
Delta
Wed, Jul 2 - Tue, Jul 8
GPT
Gulfport
ORD
Chicago
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 2 from Gulfport to Chicago, returning Tue, Jul 8, priced at $233 found 2 days ago
Delta
Sat, May 24 - Wed, May 28
GPT
Gulfport
ORD
Chicago
$237 Roundtrip, found 3 hours ago
$237
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, May 24 from Gulfport to Chicago, returning Wed, May 28, priced at $237 found 3 hours ago
Delta
Wed, May 28 - Mon, Jun 2
GPT
Gulfport
ORD
Chicago
$246 Roundtrip, found 14 hours ago
$246
Roundtrip
found 14 hours ago
Select Delta flight, departing Wed, May 28 from Gulfport to Chicago, returning Mon, Jun 2, priced at $246 found 14 hours ago
United
Thu, May 29 - Mon, Jun 2
GPT
Gulfport
ORD
Chicago
$249 Roundtrip, found 1 hour ago
$249
Roundtrip
found 1 hour ago
Select United flight, departing Thu, May 29 from Gulfport to Chicago, returning Mon, Jun 2, priced at $249 found 1 hour ago
Delta
Thu, May 29 - Mon, Jun 2
GPT
Gulfport
ORD
Chicago
$253 Roundtrip, found 1 hour ago
$253
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, May 29 from Gulfport to Chicago, returning Mon, Jun 2, priced at $253 found 1 hour ago
American Airlines
Thu, Jul 17 - Sat, Jul 19
GPT
Gulfport
ORD
Chicago
$254 Roundtrip, found 1 hour ago
$254
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Jul 17 from Gulfport to Chicago, returning Sat, Jul 19, priced at $254 found 1 hour ago
Flights from Gulfport (GPT) to Chicago (ORD)
Origin airport
Gulfport - Biloxi Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$198
Distance
801 mi

Gulfport to Chicago Flights

The cheapest times to fly from Gulfport to Chicago

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 Gulfport to Chicago are during the month of May. You can find some of the cheapest flights from Gulfport to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Gulfport to Chicago

Sunday is one of the best days to book for cheap flights from Gulfport to Chicago: 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 Gulfport to Chicago

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 Gulfport to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $100 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 Gulfport to Chicago 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 Gulfport to Chicago 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 Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from GPT to ORD 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 GPT to ORD?
The cheapest flights from GPT to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD)?
Catch a nonstop flight with Sun Country Airlines and journey straight from Gulfport - Biloxi Intl. Airport (GPT) to O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from GPT to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from GPT to ORD. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD)?
On average, Gulfport - Biloxi Intl. Airport (GPT) has 1 nonstop flights to O’Hare Intl. Airport (ORD) each week. If you’re looking for more choice, take advantage of Expedia’s filters to find flights with a layover. Squeeze in a visit to another city or simply break up your travels.
What are the most popular departure times for flights from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD)?
The 11 AM departures from GPT to ORD are the most sought after. Prices can be higher for these popular slots. If you’re looking to save, pick a less crowded time to fly.
What day of the week has the most flights from GPT to ORD?
Depart on a Sunday if you’re searching for the largest selection of flights from Gulfport - Biloxi Intl. Airport (GPT) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD)?
Take the earliest flight at around 11:15AM UTC-6, departing from Gulfport - Biloxi Intl. Airport (GPT). You’ll be traveling for about 2h 15m, coming in to land at O’Hare Intl. Airport (ORD) at approximately 1:30PM UTC-6.
How long does it take to fly from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD)?
It takes about 2 hours and 15 minutes to travel the 800 mi from GPT to ORD.
What is the best time to fly from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Gulfport - Biloxi Intl. Airport (GPT) to O’Hare Intl. Airport (ORD) route, fly before 3 PM. Departures after this hour 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.
What airports do you fly into for Chicago from Gulfport - Biloxi Intl. Airport (GPT)?
If you’re taking a direct flight from Gulfport - Biloxi Intl. Airport (GPT) to Chicago, O’Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book a ticket from GPT to ORD often results in higher prices. While you might find some last-minute deals, there’s no guarantee. Be flexible with your travel plans to boost your chances of snagging a bargain.
Is it cheaper to book a GPT to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a GPT to ORD flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one convenient place will take the hassle out of planning your trip. Just pick your flights and choose from our extensive range of stays, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Gulfport - Biloxi Intl. Airport (GPT) to O'Hare Intl. Airport (ORD)?
If you booked your GPT to ORD flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

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*Available to One Key members.