Cheap Flights from Chicago (ORD) to Gulf Shores (GUF)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards)

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Flights from Chicago (ORD) to Gulf Shores (GUF)
Origin airport
O'Hare Intl.
Destination airport
Jack Edwards
Distance
807 mi

Chicago to Gulf Shores Flights

The cheapest times to fly from Chicago to Gulf Shores

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

 

The best time to book a flight from Chicago to Gulf Shores

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

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 Gulf Shores in 2026. You can also book with separate airlines for your outbound and return journeys, from 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 Gulf Shores 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 Gulf Shores 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 O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards) cost?
Lock in a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards) 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 Gulf Shores, AL (GUF-Jack Edwards)?
is the most affordable month to fly from ORD to GUF. Traveling during an off-peak travel window is often the key to finding better deals on flights.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards)?
To find the cheapest airline flying from ORD to GUF, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards)?
Direct flights from O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to GUF?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can vary depending on a range of factors, including the carrier and season.*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 Gulf Shores, AL (GUF-Jack Edwards)?
To land at Gulf Shores, AL (GUF-Jack Edwards) on time, choose a flight that leaves from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Gulf Shores from O'Hare Intl. Airport (ORD)?
Pensacola Intl. Airport (PNS) is the only airport in Gulf Shores with direct flights from O'Hare Intl. Airport (ORD). Check out the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards) last-minute?
Waiting until just before your departure to book a flight from ORD to GUF often results in higher prices. While you may find some last-minute discounts, they're not always guaranteed. Be flexible with your itinerary to maximize your chances of landing a bargain.
Is it cheaper to book an ORD to GUF flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to GUF flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one place will take the hassle out of travel planning. Simply pick your flights and choose from our wide range of hotels, then customize your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Gulf Shores, AL (GUF-Jack Edwards)?
Typically, you can reschedule or cancel your ORD to GUF 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 guidelines on flight changes, or if you'd like more details, go to our Customer Service portal.

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*Available to One Key members.