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

Flights from Chicago (MDW) to Gulf Shores (GUF)
Origin airport
Midway Intl.
Destination airport
Jack Edwards
Distance
794 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 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.

Frequently asked questions

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to GUF last minute?
Being the spontaneous type is a fabulous way to explore the globe, but it’s not necessarily the smartest way to land a cheap plane ticket. Consider booking your Midway Intl. Airport (MDW) to GUF journey well in advance rather than waiting till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. You can unleash your spontaneous side when you arrive in GUF!
What airports do you fly into for Gulf Shores from Chicago?
With Gulf Shores, AL (GUF-Jack Edwards), Pensacola Intl. Airport (PNS) and Mobile Regional Airport (MOB) to pick from, traveling from Chicago to Gulf Shores is no sweat. The city’s main terminal, Gulf Shores, AL (GUF-Jack Edwards), is about 3 mi north of the center. Along with ticket costs, consider things like the ease of getting from the airport and the distance to your hotel when deciding where to touch down. Get your Gulf Shores trip off to an exciting start by checking out Gulf Shores Beach and The Wharf.
Can I change the date of my flight from Midway Intl. Airport (MDW) to GUF?
Quickly and easily make changes to your Chicago Airport to GUF flight via the Expedia Trips portal. But before doing so, read through the fare rules in your itinerary to find out what the carrier will allow you to do and if charges apply. Some airlines have a change fee per person, plus any difference in ticket prices. However, if you booked in the last 24 hours, you may be able to cancel for free and organize new flights. You can also head to our Customer Service portal for more advice and to connect with our Virtual Agent.

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*Available to One Key members.