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By Huuk Team

Road trip from Chicago to Montgomery

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Show more (3+)

ITINERARY

14h 1m750 miles17 stops
1
Museum Of Illusions Chicago
25 E Washington St, Chicago, IL 60602-1708
2
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.
3
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.
4
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
5
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.
6
The Grill
9755 Fall Creek Rd, Indianapolis, IN 46256-4713
7
Angel's Envy Distillery
500 E Main Street, Louisville, KY 40202-1002
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
8
Amber Falls Winery Nashville
349 Opry Mills Dr Suite 751A, Nashville, TN 37214-2437
Amber Falls Winery Nashville is proud and excited to be the first and only winery at Opry Mills Mall! We are a satellite store for Amber Falls Winery & Cellars in Hampshire, TN. Our mission is to bring the same exceptional customer service and award-winning wine to Nashville! We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. Something new that we are excited about is selling our delicious WineTeaZers in growlers! Enjoy it anywhere and then bring your growler back for more! So swing by and taste some of our wine, sit and sip on a glass with friends and then take a few bottles home to enjoy!
9
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.
10
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.
11
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.
12
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.
13
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.
14
ZYDECO
2001 15th Ave S, Birmingham, AL 35205-3811
15
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.
16
The Davis Theatre
251 Montgomery St, Montgomery, AL 36104-3526
17
GTSouth Geek & Gaming Tavern
4017 Eastern Blvd, Montgomery, AL 36116-7307
GTSouth is the Geek & Gamer haven. In addition to amazing cocktails, you will find video games, board games, karaoke, anime, Doctor Who, and a great little community of people who love the same things you do. Theme nights including Cosplay, Nerf Nights, and other themes happen throughout the year. GTSouth is a non-smoking bar however we are Vaping friendly and carry our own line of Vaping juices. Come hang out at the most unique bar in Montgomery, AL!
Customize this Trip

OVERVIEW

All aboard for an epic adventure from the bustling metropolis of Chicago to the captivating city of Montgomery! Our journey will traverse a tapestry of landscapes, each with its unique charm. As we glide through the heartland of America, we'll witness verdant farmlands, mighty rivers, and rolling hills unfolding before our eyes.

Along the way, we'll delve into the rich history and culture that shaped both Chicago and Montgomery. From the iconic skyscrapers of the Windy City to the vibrant streets of the Deep South, we'll uncover the stories and traditions that make these destinations so special. Whether you're a history buff, a nature enthusiast, or simply someone who loves to explore new places, this journey has something for everyone.

As we approach Montgomery, the birthplace of the Civil Rights Movement, we'll be inspired by the legacy of those who fought for equality and justice. Our adventure culminates in this historic city, where we'll reflect on the past and look forward to a brighter future. Get ready to immerse yourself in the beauty, history, and culture that awaits us on this unforgettable journey from Chicago to Montgomery.

1
Start:Museum Of Illusions Chicago
Chicago, Illinois·
4.5
(97) review
25 E Washington St, Chicago, IL 60602-1708
2
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
3
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
4
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
5
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
6
The Grill
Indianapolis, Indiana·
3.5
(9) review
9755 Fall Creek Rd, Indianapolis, IN 46256-4713
7
Angel's Envy Distillery
Louisville, Kentucky·
4.5
(967) review
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
500 E Main Street, Louisville, KY 40202-1002
8
Amber Falls Winery Nashville
Nashville, Davidson County, Tennessee·
4.5
(9) review
Amber Falls Winery Nashville is proud and excited to be the first and only winery at Opry Mills Mall! We are a satellite store for Amber Falls Winery & Cellars in Hampshire, TN. Our mission is to bring the same exceptional customer service and award-winning wine to Nashville! We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. We offer wine tastings, wine by the glass and also sell our fabulous wine by the bottle. Something new that we are excited about is selling our delicious WineTeaZers in growlers! Enjoy it anywhere and then bring your growler back for more! So swing by and taste some of our wine, sit and sip on a glass with friends and then take a few bottles home to enjoy!
349 Opry Mills Dr Suite 751A, Nashville, TN 37214-2437
9
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
10
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
11
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
12
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
13
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
14
ZYDECO
Birmingham, Alabama·
2.5
(9) review
2001 15th Ave S, Birmingham, AL 35205-3811
15
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
16
The Davis Theatre
Montgomery, Alabama·
4.5
(8) review
251 Montgomery St, Montgomery, AL 36104-3526
17
GTSouth Geek & Gaming Tavern
Montgomery, Alabama·
5.0
(8) review
GTSouth is the Geek & Gamer haven. In addition to amazing cocktails, you will find video games, board games, karaoke, anime, Doctor Who, and a great little community of people who love the same things you do. Theme nights including Cosplay, Nerf Nights, and other themes happen throughout the year. GTSouth is a non-smoking bar however we are Vaping friendly and carry our own line of Vaping juices. Come hang out at the most unique bar in Montgomery, AL!
4017 Eastern Blvd, Montgomery, AL 36116-7307

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Montgomery?
The distance is 750 miles
What's the travel time between Chicago and Montgomery?
The driving time can vary depending on traffic conditions, but it is typically 14h 1m mins in normal traffic
What are some of the best cities to visit between Chicago and Montgomery?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Montgomery?
There are plenty! Here are some stops you shouldn’t miss on your way to Montgomery
What’s the weather like in Montgomery?
The weather in Montgomery is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Montgomery in January
Weather in Montgomery in February
Weather in Montgomery in March
Weather in Montgomery in April
Weather in Montgomery in May
Weather in Montgomery in June
Weather in Montgomery in July
Weather in Montgomery in August
Weather in Montgomery in September
Weather in Montgomery in October
Weather in Montgomery in November
Weather in Montgomery in December
Interested in a detailed plan for your time in Montgomery?
Plan your dream Montgomery trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Montgomery
A 2-day itinerary in Montgomery
A 3-day itinerary in Montgomery
A 4-day itinerary in Montgomery
A 5-day itinerary in Montgomery
A 6-day itinerary in Montgomery
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
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