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By Huuk Team

Road trip from Chicago to Gulfport

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iconOutdoor Activities
iconSights & Landmarks
iconFood & Drink
iconConcerts & Shows
iconFun & Games
iconClasses & Workshops

ITINERARY

16h 37m889 miles8 stops
1
The Chopping Block
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
2
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
3
Boystown
Chicago, IL
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
4
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
5
The Quarry at Crystal Springs
1 Crystal Springs Quarry Dr, Maryland Heights, Saint Louis, MO 63043-0015
6
Overton Park
1914 Poplar Ave, Memphis, TN 38104-2806
Overton Park is a 342-acre public park in Memphis, Tennessee. The park is home to two playgrounds, a dog park, an open Greensward for recreation, a Veterans Plaza, and the 126-acre Old Forest State Natural Area. It features more than eight miles of trails, including the Bike Gate arch and plaza trail. The park is managed by the nonprofit Overton Park Conservancy. Overton Park is also a major cultural attraction, home to a nine-hole golf course, Memphis Brooks Museum of Art, the Memphis Zoo, Memphis College of Art, and the Levitt Shell concert pavilion.
7
Blues Hall Juke Joint
174 Beale St, Memphis, TN 38103-3714
8
Cooper-Young Historic District
Cooper and Young Streets, Memphis, TN 38101
Customize this Trip

OVERVIEW

Come along on an unforgettable adventure from the vibrant streets of Chicago to the sun-kissed shores of Gulfport. Our journey will traverse a tapestry of landscapes, from towering skyscrapers to rolling hills and tranquil waters. As we embark on this epic voyage, the rhythm of the rails will serenade us, connecting us to the heartland of America and the allure of the Gulf Coast.

Throughout our odyssey, history will unfold before our eyes. We'll delve into the bustling energy of Chicago, a city where dreams soar and innovation thrives. The charm of quaint towns will captivate us, inviting us to embrace their timeless stories and local flavors. As we journey southward, the landscape will transform, revealing the grandeur of nature's tapestry. Verdant forests will whisper secrets, while sparkling rivers and majestic mountains will ignite our sense of wonder.

Embracing the embrace of the Gulf Coast, we'll bask in the warmth of its sandy beaches and revel in the vibrant hues of its sunsets. The salty tang of the ocean breeze will invigorate our spirits, as we succumb to the allure of this coastal paradise. From bustling metropolises to serene coastal retreats, our journey from Chicago to Gulfport promises an extraordinary symphony of experiences, where the past, present, and future intertwine in a captivating tapestry of Americana.

1
Start:The Chopping Block
Chicago, Illinois·
4.5
(98) review
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
2
Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
333 Michigan Ave, Chicago, IL 60601-3901
3
Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
Chicago, IL
4
Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
1060 W. Addison St., Chicago, IL 60613-4566
5
The Quarry at Crystal Springs
Maryland Heights, Saint Louis, Missouri·
4.0
(5) review
1 Crystal Springs Quarry Dr, Maryland Heights, Saint Louis, MO 63043-0015
6
Overton Park
Memphis, Tennessee·
4.5
(92) review
Overton Park is a 342-acre public park in Memphis, Tennessee. The park is home to two playgrounds, a dog park, an open Greensward for recreation, a Veterans Plaza, and the 126-acre Old Forest State Natural Area. It features more than eight miles of trails, including the Bike Gate arch and plaza trail. The park is managed by the nonprofit Overton Park Conservancy. Overton Park is also a major cultural attraction, home to a nine-hole golf course, Memphis Brooks Museum of Art, the Memphis Zoo, Memphis College of Art, and the Levitt Shell concert pavilion.
1914 Poplar Ave, Memphis, TN 38104-2806
7
Blues Hall Juke Joint
Memphis, Tennessee·
4.5
(97) review
174 Beale St, Memphis, TN 38103-3714
8
Cooper-Young Historic District
Memphis, Tennessee·
4.0
(97) review
Cooper and Young Streets, Memphis, TN 38101

CHECKLIST

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Car charger and portable battery
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Water bottles and snacks
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Travel pillow and blanket
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Sunglasses and sunscreen
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First-aid kit
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Hand sanitizer and wet wipes
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Driver’s license and vehicle registration
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Cash and cards
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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Gulfport?
The distance is 889 miles
What's the travel time between Chicago and Gulfport?
The driving time can vary depending on traffic conditions, but it is typically 16h 37m mins in normal traffic
What are some of the best cities to visit between Chicago and Gulfport?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Gulfport?
There are plenty! Here are some stops you shouldn’t miss on your way to Gulfport
What’s the weather like in Gulfport?
The weather in Gulfport is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Gulfport in January
Weather in Gulfport in February
Weather in Gulfport in March
Weather in Gulfport in April
Weather in Gulfport in May
Weather in Gulfport in June
Weather in Gulfport in July
Weather in Gulfport in August
Weather in Gulfport in September
Weather in Gulfport in October
Weather in Gulfport in November
Weather in Gulfport in December
Interested in a detailed plan for your time in Gulfport?
Plan your dream Gulfport trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Gulfport
A 2-day itinerary in Gulfport
A 3-day itinerary in Gulfport
A 4-day itinerary in Gulfport
A 5-day itinerary in Gulfport
A 6-day itinerary in Gulfport
Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you