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

Popular airlines from Chicago Midway Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards)

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards) cost?
Lock in a cheap one-way flight or cheap return flight from Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards)?
Flying in is a great way to save, as it's the cheapest month for flights between MDW and GUF. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to GUF flight.
How many flights per day from Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards)?
Direct flights from Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards) 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 travel dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to GUF?
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 peak travel times or public holidays.*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 Gulf Shores, AL (GUF-Jack Edwards)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards) route, aim to fly before 3 PM. Departures after this hour have a 22% higher chance of being 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 Gulf Shores, AL (GUF-Jack Edwards) last-minute?
Booking your ticket from MDW to GUF right before your trip is usually more expensive. However, if you're flexible with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to GUF flight and hotel package?
You can save money by securing a MDW to GUF flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After choosing your preferred accommodations and flights, consider adding extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Gulf Shores, AL (GUF-Jack Edwards)?
It's generally possible to reschedule or cancel your MDW to GUF flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Jack Edwards
Distance
794 mi

Book with confidence

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 2025. 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.

 

Chicago to Gulf Shores Flights

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*Available to One Key members.