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By Huuk Team

Road trip from Chicago to Pensacola

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Show more (2+)

ITINERARY

17h 10m910 miles11 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 Grill
9755 Fall Creek Rd, Indianapolis, IN 46256-4713
6
Tennessee State Museum
1000 Rosa L Parks Blvd, Nashville, TN 37208-2624
The Tennessee State Museum is located at the corner of Rosa L. Parks Blvd. and Jefferson Street at Bicentennial Capitol Mall State Park. It is designed to bring history to life. It includes a “Tennessee Time Tunnel” chronicling the state’s rich history and leading visitors though the Museum’s permanent collection, a hands-on children’s gallery, six rotating galleries, a state-of-the art digital learning center and a two-story Grand Hall. Exhibitions include significant artifacts related to the state’s history, along with displays of art, furniture, textiles, and photographs produced by Tennesseans. The Museum's Civil War holdings of uniforms, battle flags and weapons are among the finest in the nation.There is no admission charge for visitors. Hours are subject to change. Please check our website at tnmuseum.org for the most up to date information on parking, exhibitions and events.
7
Bicentennial Capitol Mall State Park
600 James Robertson Pkwy, Nashville, TN 37243-3081
This 19 acre park in the heart of Nashville serves as a monument to the bicentennial celebration of the State of Tennessee. This park offers plenty of opportunities to learn about the long history of Tennessee while having a great experience in a beautiful green space. More information on this park and many more can be found at the TN State Parks website.
8
Jackalope Brewing Company - The Ranch
429B Houston St, Nashville, TN 37203-4832
Jackalope Brewing Company's taproom and brewery The Ranch offers locally hand-crafted beers, brewery tours, small bites, and a dog-friendly outdoor patio.
9
Lane Motor Museum
702 Murfreesboro Pike, Nashville, TN 37210-4522
Lane Motor Museum in Nashville features the largest European collection of cars and motorcycles in the United States. Admission for adults aged 18-64 is $15; Admission for Youths aged 6-17 is $3; Admission for seniors 65+ is $10; Children under 5 are always free. There is plenty of FREE parking.
10
McWane Science Center
200 19th St N, Birmingham, AL 35203-3117
Fun and learning never end at McWane Science Center, a nonprofit, hands-on museum and IMAX(R) Dome Theater. Four floors of interactive exhibits celebrate science and wonder - from an amazing collection of dinosaurs to innovative environmental showcases, imaginative early childhood playgrounds, and an awe-inspiring aquarium. The energy and excitement of discovery spring to life through an extensive lineup of science demonstrations performed daily by talented educators. The adventure intensifies in the IMAX(R) Dome Theater, where wide-eyed visitors experience the sights and sounds of breathtaking films on a 5-story-tall screen surrounded by 3 tons of high-intensity speakers.
11
Statue of Liberty Replica
Liberty Parkway Liberty Park, Birmingham, AL 35242
Bronze replica measuring one-fifth the size of its sister statue located in New York City.
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OVERVIEW

Get ready for an epic adventure, starting in the bustling city of Chicago and ending in the sun-kissed beaches of Pensacola! We'll traverse vast landscapes, witness iconic landmarks, and create memories that will last a lifetime. Along the way, we'll unravel the rich history of the places we visit, from the vibrant streets of Chicago to the charming coastal towns of the Gulf Coast.

Our journey will take us through diverse ecosystems, from lush forests to rolling hills and sparkling waterways. We'll marvel at towering skyscrapers and quaint villages, each with its own unique story to tell. As we venture south, the scenery gradually transforms, welcoming us to the serene shores and emerald waters of the Gulf of Mexico.

Prepare to be captivated by the vibrant culture and friendly locals we encounter throughout our adventure. From the bustling markets of Chicago to the laid-back atmosphere of Pensacola, we'll immerse ourselves in the local way of life, savoring delicious cuisine, listening to captivating stories, and making connections that will stay with us long after our journey ends.

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 Grill
Indianapolis, Indiana·
3.5
(9) review
9755 Fall Creek Rd, Indianapolis, IN 46256-4713
6
Tennessee State Museum
Nashville, Davidson County, Tennessee·
4.5
(997) review
The Tennessee State Museum is located at the corner of Rosa L. Parks Blvd. and Jefferson Street at Bicentennial Capitol Mall State Park. It is designed to bring history to life. It includes a “Tennessee Time Tunnel” chronicling the state’s rich history and leading visitors though the Museum’s permanent collection, a hands-on children’s gallery, six rotating galleries, a state-of-the art digital learning center and a two-story Grand Hall. Exhibitions include significant artifacts related to the state’s history, along with displays of art, furniture, textiles, and photographs produced by Tennesseans. The Museum's Civil War holdings of uniforms, battle flags and weapons are among the finest in the nation.There is no admission charge for visitors. Hours are subject to change. Please check our website at tnmuseum.org for the most up to date information on parking, exhibitions and events.
1000 Rosa L Parks Blvd, Nashville, TN 37208-2624
7
Bicentennial Capitol Mall State Park
Nashville, Davidson County, Tennessee·
4.5
(969) review
This 19 acre park in the heart of Nashville serves as a monument to the bicentennial celebration of the State of Tennessee. This park offers plenty of opportunities to learn about the long history of Tennessee while having a great experience in a beautiful green space. More information on this park and many more can be found at the TN State Parks website.
600 James Robertson Pkwy, Nashville, TN 37243-3081
8
Jackalope Brewing Company - The Ranch
Nashville, Davidson County, Tennessee·
4.5
(9) review
Jackalope Brewing Company's taproom and brewery The Ranch offers locally hand-crafted beers, brewery tours, small bites, and a dog-friendly outdoor patio.
429B Houston St, Nashville, TN 37203-4832
9
Lane Motor Museum
Nashville, Davidson County, Tennessee·
4.5
(971) review
Lane Motor Museum in Nashville features the largest European collection of cars and motorcycles in the United States. Admission for adults aged 18-64 is $15; Admission for Youths aged 6-17 is $3; Admission for seniors 65+ is $10; Children under 5 are always free. There is plenty of FREE parking.
702 Murfreesboro Pike, Nashville, TN 37210-4522
10
McWane Science Center
Birmingham, Alabama·
4.5
(963) review
Fun and learning never end at McWane Science Center, a nonprofit, hands-on museum and IMAX(R) Dome Theater. Four floors of interactive exhibits celebrate science and wonder - from an amazing collection of dinosaurs to innovative environmental showcases, imaginative early childhood playgrounds, and an awe-inspiring aquarium. The energy and excitement of discovery spring to life through an extensive lineup of science demonstrations performed daily by talented educators. The adventure intensifies in the IMAX(R) Dome Theater, where wide-eyed visitors experience the sights and sounds of breathtaking films on a 5-story-tall screen surrounded by 3 tons of high-intensity speakers.
200 19th St N, Birmingham, AL 35203-3117
11
Statue of Liberty Replica
Birmingham, Alabama·
4.0
(97) review
Bronze replica measuring one-fifth the size of its sister statue located in New York City.
Liberty Parkway Liberty Park, Birmingham, AL 35242

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Pensacola?
The distance is 910 miles
What's the travel time between Chicago and Pensacola?
The driving time can vary depending on traffic conditions, but it is typically 17h 10m mins in normal traffic
What are some of the best cities to visit between Chicago and Pensacola?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Pensacola?
There are plenty! Here are some stops you shouldn’t miss on your way to Pensacola
What’s the weather like in Pensacola?
The weather in Pensacola is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Pensacola in January
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Weather in Pensacola in December
Interested in a detailed plan for your time in Pensacola?
Plan your dream Pensacola trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Pensacola
A 2-day itinerary in Pensacola
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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