HomeExperience the Best Vacation From Chicago to Gulf Shores, ALExperience the Best Vacation From Chicago to Gulf Shores, AL

It’s no secret that Chicago is known as “The Windy City” and has lots of chilly weather? Are you craving a getaway to the warm and sunny Gulf Coast? Pack your bags and head to Gulf Shores, Alabama! Our quirky beach town is filled with fun-filled adventures, lively bars, and a delicious culinary scene. It doesn’t get any better than that! Learn how you can have the ultimate escape from Chicago to Gulf Shores 

After reading this blog, you’ll know all the details about the trip from Chicago, IL, to Gulf Shores, AL. Now you need to start figuring out the rest of the exciting details! Check out our accommodations to find the perfect vacation home for your stay. Plus, let our team do the activity searching for you, so you can focus on what matters most: making unforgettable memories with your loved ones.

Getaway From Chicago to Gulf Shores 

With our help, planning a trip from Chicago to Gulf Shores is as easy as 1, 2, 3! 

1. Reserve Your Dream Vacation Rental 

vacation rental

You can’t plan a trip without a place to rest your head and make your home base. When it comes to vacation rentals in Gulf Shores, Harris Vacation Rentals is your headquarters. We offer top-notch vacation rentals in beach towns along the coast, including Gulf Shores, Fort Morgan, and Orange Beach. Each property ranges in size and price, so it’s easy to find the perfect place for you. 

Each of our rental properties features five-star amenities to make you feel at home. Whether you want a private pool, elevator, covered deck, game room, or breathtaking beach views, we’ve got you covered here. With the help of Harris Vacation Rentals, the ultimate getaway awaits! 

2. Book Your Travel 


Now it’s time to figure out your travel plans. The distance from Chicago to Gulf Shores is about 940 miles. So that means the driving time is roughly 14 ½ hours long. That is a bit of a long road trip—but if that’s your preferred journey, then go for it! If the drive from Chicago to Gulf Shores is too much for you, booking a flight is your best move.  

The best way to fly from Chicago to Gulf Shores is to leave from O’Hare International Airport (ORD) and fly into Pensacola International Airport (PNS). You’ll find an array of airlines to choose from that offer connecting flights between the two airports. These airlines include United, Delta, Spirit, Southwest, and more. 

After you arrive at the Pensacola airport, it’s time to make your way to Gulf Shores. The driving distance from Pensacola to Gulf Shores is just under 40 miles and only about an hour long. Rent a car, hop in a cab, or order an Uber and head for the coast! 

3. Make the Most Out of Your Stay at the Beach 

You did it! You’ve arrived in our one-of-a-kind beach town of Gulf Shores. How will you make the most out of your stay here? Our town is filled with endless things to do and see. Whether you’re focused on relaxing in the sand, indulging in the delicious local food scene, or checking out unique attractions and outdoor adventures, we’ve got you covered here. These are some of the most popular things to do in Gulf Shores: 


One of the best parts of any trip is indulging in new restaurants. After all, calories don’t’ count when you’re on vacation—right?! Some of the most popular eateries in the area include: 


Make Your Getaway Happen 

Now you know everything about the perfect vacation from Chicago to Gulf Shores. It’s time to make it happen! Browse our collection of vacation rentals and find the perfect one for you. We can’t wait to host you on your Alabama Gulf Coast retreat!