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By Huuk Team

Road trip from Chicago to The Woodlands

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ITINERARY

19h 36m1,057 miles17 stops
1
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.
2
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
3
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.
4
The Quarry at Crystal Springs
1 Crystal Springs Quarry Dr, Maryland Heights, Saint Louis, MO 63043-0015
5
Robinson Center
Markham At Broadway, Little Rock, AR 72201
6
Mystery Mansion Escape Room
2122 S Broadway St, Little Rock, AR 72206-1356
Interactive Game of sleuthing intelligence. Bring your family, friends, or convention attendees for 60 minutes of sheer, heart pumping entertainment. Push your mind to its limits as you solve puzzles, find clues and crack codes to escape your fate. Great for team building, entertainment, date night and special occasions. Check out our website for details. Private bookings available. Hours Vary - Book online By Reservation Only. Children of any age are welcome to attend with family in a private room. For specific information, check out our FAQs on the website or feel free to call.
7
Children's Library and Learning Center
4800 W 10th St, Little Rock, AR 72204-1807
8
Proud Mary's Bar And Grill Shreveport, La.
3155 N Market St Ste 100, Shreveport, LA 71101-3237
9
Walter B Jacobs Memorial Nature Park
8012 Blanchard Furrh Rd, Shreveport, LA 71107-8310
A nature park featuring over 5 miles of forested hiking trails. A visitor center with exhibits and live animals and an outdoor aviary featuring live birds of prey, including a bald eagle and several species of owls. Public programs, events, and festivals are held regularly and are always free of charge. Tours and classes are offered for groups by reservation.
10
Gardens of the American Rose Center
Jefferson Paige Road Interstate 20 Exit # 8, Shreveport, LA 71119
Operated by the American Rose Society, the 42 acres of this research and garden facility feature 20,000 blooms.
11
C. Bickham Dickson Park
2283 Bert Kouns, Shreveport, LA 71105
12
Splash Kingdom Waterpark
7670 W 70th St, Shreveport, LA 71129-2204
Splash Kingdom is a family friendly waterpark that offers plenty of summer fun for everyone. There are wave pools, slides, children's areas and a lazy river for those who want to just relax.
13
Klaus Brewing
10142 Jones Rd, Houston, TX 77065-5680
14
Great Heights Brewing Company
938 Wakefield Dr, Houston, TX 77018-6204
15
Houston Grand Opera
500 Texas St (Wortham Center), Houston, TX 77002-2737
Opera house in Houston that features opera presentations throughout the year.
16
The Menil Collection
1533 Sul Ross St, Houston, TX 77006-4729
Houston philanthropists and art patrons John and Dominique de Menil established the Menil Foundation in 1954 to foster greater public understanding and appreciation of art, architecture, culture, religion, and philosophy. In 1987, the Menil Collection’s main museum building opened to the public. Today, the Menil Collection consists of a group of five art buildings and green spaces located within a residential neighborhood. The Menil remains committed to its founders’ belief that art is essential to human experience and fosters direct personal encounters with works of art. The museum welcomes all visitors free of charge to its buildings and surrounding green spaces.
17
Lillie and Hugh Roy Cullen Sculpture Garden
900 Bissonnet St, Houston, TX 77005
Customize this Trip

OVERVIEW

Prepare yourself for an epic adventure as we embark on an unforgettable road trip from the bustling metropolis of Chicago to the tranquil town of The Woodlands. Along the way, we'll traverse a tapestry of landscapes, each with its own unique charm. From the towering skyscrapers and vibrant streets of the Windy City to the rolling hills and serene forests of rural America, every mile promises a new vista to behold.

As we leave Chicago behind, we'll journey through the heartland of the Midwest. Quaint towns and sprawling farmlands will greet us as we make our way towards the Mississippi River. Crossing this mighty waterway, we'll enter the realm of the South, where the pace of life slows and the air is filled with the sweet scent of magnolia blossoms.

Finally, we'll approach our destination: The Woodlands, a picturesque town nestled amidst towering pines and sparkling lakes. As we arrive, we'll have traveled hundreds of miles, creating memories that will last a lifetime. This road trip will not only be a journey of distance but also a journey of discovery, as we explore the diverse beauty and rich culture that America has to offer.

1
Start: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
2
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
3
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
4
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
5
Robinson Center
Little Rock, Arkansas·
4.5
(99) review
Markham At Broadway, Little Rock, AR 72201
6
Mystery Mansion Escape Room
Little Rock, Arkansas·
5.0
(901) review
Interactive Game of sleuthing intelligence. Bring your family, friends, or convention attendees for 60 minutes of sheer, heart pumping entertainment. Push your mind to its limits as you solve puzzles, find clues and crack codes to escape your fate. Great for team building, entertainment, date night and special occasions. Check out our website for details. Private bookings available. Hours Vary - Book online By Reservation Only. Children of any age are welcome to attend with family in a private room. For specific information, check out our FAQs on the website or feel free to call.
2122 S Broadway St, Little Rock, AR 72206-1356
7
Children's Library and Learning Center
Little Rock, Arkansas·
4.5
(9) review
4800 W 10th St, Little Rock, AR 72204-1807
8
Proud Mary's Bar And Grill Shreveport, La.
Shreveport, Louisiana·
3.5
(9) review
3155 N Market St Ste 100, Shreveport, LA 71101-3237
9
Walter B Jacobs Memorial Nature Park
Shreveport, Louisiana·
4.5
(33) review
A nature park featuring over 5 miles of forested hiking trails. A visitor center with exhibits and live animals and an outdoor aviary featuring live birds of prey, including a bald eagle and several species of owls. Public programs, events, and festivals are held regularly and are always free of charge. Tours and classes are offered for groups by reservation.
8012 Blanchard Furrh Rd, Shreveport, LA 71107-8310
10
Gardens of the American Rose Center
Shreveport, Louisiana·
3.5
(85) review
Operated by the American Rose Society, the 42 acres of this research and garden facility feature 20,000 blooms.
Jefferson Paige Road Interstate 20 Exit # 8, Shreveport, LA 71119
11
C. Bickham Dickson Park
Shreveport, Louisiana·
2.5
(6) review
2283 Bert Kouns, Shreveport, LA 71105
12
Splash Kingdom Waterpark
Shreveport, Louisiana·
3.5
(118) review
Splash Kingdom is a family friendly waterpark that offers plenty of summer fun for everyone. There are wave pools, slides, children's areas and a lazy river for those who want to just relax.
7670 W 70th St, Shreveport, LA 71129-2204
13
Klaus Brewing
Houston, Texas·
4.0
(9) review
10142 Jones Rd, Houston, TX 77065-5680
14
Great Heights Brewing Company
Houston, Texas·
4.0
(9) review
938 Wakefield Dr, Houston, TX 77018-6204
15
Houston Grand Opera
Houston, Texas·
4.5
(94) review
Opera house in Houston that features opera presentations throughout the year.
500 Texas St (Wortham Center), Houston, TX 77002-2737
16
The Menil Collection
Houston, Texas·
4.5
(970) review
Houston philanthropists and art patrons John and Dominique de Menil established the Menil Foundation in 1954 to foster greater public understanding and appreciation of art, architecture, culture, religion, and philosophy. In 1987, the Menil Collection’s main museum building opened to the public. Today, the Menil Collection consists of a group of five art buildings and green spaces located within a residential neighborhood. The Menil remains committed to its founders’ belief that art is essential to human experience and fosters direct personal encounters with works of art. The museum welcomes all visitors free of charge to its buildings and surrounding green spaces.
1533 Sul Ross St, Houston, TX 77006-4729
17
Lillie and Hugh Roy Cullen Sculpture Garden
Houston, Texas·
4.5
(96) review
900 Bissonnet St, Houston, TX 77005

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and The Woodlands?
The distance is 1,057 miles
What's the travel time between Chicago and The Woodlands?
The driving time can vary depending on traffic conditions, but it is typically 19h 36m mins in normal traffic
What are some of the best cities to visit between Chicago and The Woodlands?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to The Woodlands?
There are plenty! Here are some stops you shouldn’t miss on your way to The Woodlands
What’s the weather like in The Woodlands?
The weather in The Woodlands is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in The Woodlands in January
Weather in The Woodlands in February
Weather in The Woodlands in March
Weather in The Woodlands in April
Weather in The Woodlands in May
Weather in The Woodlands in June
Weather in The Woodlands in July
Weather in The Woodlands in August
Weather in The Woodlands in September
Weather in The Woodlands in October
Weather in The Woodlands in November
Weather in The Woodlands in December
Interested in a detailed plan for your time in The Woodlands?
Plan your dream The Woodlands trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in The Woodlands
A 2-day itinerary in The Woodlands
A 3-day itinerary in The Woodlands
A 4-day itinerary in The Woodlands
A 5-day itinerary in The Woodlands
A 6-day itinerary in The Woodlands
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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