This amazing road trip is full of beautiful scenery and one-of-a-kind places to see. You’ll pass by serene lakes, rolling green hills, and charming small towns. Along the way, there are plenty of opportunities to stop and take in the sights or grab a bite to eat at a local restaurant.
Once you reach your destination, you’ll have plenty to keep you entertained. You could explore the area's many museums, take a walk through the picturesque downtown, or catch a thrilling sporting event. No matter what you choose to do, you're sure to have an unforgettable adventure.
The drive itself is approximately 227 miles and takes about 3 hours and 30 minutes without stops. So, sit back, relax, and enjoy the ride. The journey is just as exciting as the destination!

Chicago

Chicago to Green Bay

Museums

Sights & Landmarks

Classes & Workshops

Other

Concerts & Shows

Food & Drink

Nature & Parks

Spas & Wellness

Shopping

Green Bay

Aboard the train, you'll have access to a variety of amenities to keep you comfortable and entertained during your journey. Each seat is equipped with a personal entertainment system, so you can watch movies, play games, or listen to music. There's also a dining car where you can purchase meals and snacks, as well as a lounge car where you can relax and socialize with other passengers.
The train will make several stops along the way, giving you the opportunity to stretch your legs and explore different cities. You'll have time to visit museums, historical sites, and other attractions. You can also take advantage of the train's Wi-Fi service to stay connected with friends and family back home.
At the end of your journey, you'll arrive in Enterprise, where you can continue your travels or simply relax and enjoy the scenery. The choice is yours!

Chicago to Enterprise

Outdoor Activities

Fun & Games

Water & Amusement Parks

Nightlife

Tours

Enterprise

Get ready for an unforgettable adventure from the bustling streets of Indianapolis to the vibrant shores of Milwaukee! Embark on a journey that weaves through picturesque landscapes, charming towns, and historic landmarks. Along the way, you'll uncover hidden gems, immerse yourself in local cultures, and create memories that will last a lifetime.
Witness the transformation of the scenery as you leave the urban sprawl behind and enter a realm of rolling hills, tranquil lakes, and verdant forests. Discover quaint villages nestled amidst towering trees, where time seems to stand still and the pace of life slows down. Marvel at architectural wonders that tell tales of the past and inspire awe in the present.
As you approach the shores of Lake Michigan, a vibrant metropolis awaits your arrival. Explore its vibrant arts scene, indulge in culinary delights, and revel in the lively atmosphere. From towering skyscrapers to charming neighborhoods, Milwaukee offers a captivating blend of urban excitement and Midwestern charm. Let the spirit of adventure guide you as you embark on this incredible journey from Indianapolis to Milwaukee, where every mile holds a promise of discovery and delight.

Indianapolis

Indianapolis to Milwaukee

Milwaukee

Miami

Miami to Milwaukee

Prepare to embark on an exciting adventure as we journey from the bustling metropolis of Chicago to the serene landscapes surrounding Spring Valley. Along the way, we'll witness a captivating tapestry of urban and rural life, where towering skyscrapers give way to rolling hills and tranquil waterways.
The journey will unfold like a captivating storybook, each chapter revealing a new and inspiring vista. As we leave the concrete jungle behind, we'll traverse verdant farmlands, where crops dance in the breeze and livestock graze peacefully. Quaint towns and hidden gems will beckon us to explore their unique charms, offering a glimpse into the rich cultural heritage that defines this region.
Our destination, Spring Valley, awaits with open arms, promising a tranquil haven amidst nature's embrace. Surrounded by pristine lakes and lush forests, it's a place where time seems to slow down, inviting us to reconnect with the simple pleasures of life. As we delve deeper into this idyllic setting, we'll discover hidden trails, glistening waterfalls, and abundant wildlife that will captivate our senses and create memories that will last a lifetime.

Chicago to Spring Valley

Spring Valley

Hop aboard an unforgettable adventure as we embark on a journey through the heart of the Midwest, from the bustling metropolis of Chicago to the picturesque city of St. Paul. Along the way, we'll traverse rolling hills, glistening lakes, and charming towns, each with its own unique story to tell.
Our adventure begins in the vibrant city of Chicago, a hub of culture, architecture, and entertainment. From the iconic Willis Tower to the bustling Magnificent Mile, Chicago offers a captivating blend of urban excitement and historical charm. As we venture northward, we'll pass through the serene landscapes of Illinois and Wisconsin, where lush greenery and sparkling waterways create a tranquil backdrop. The gentle rhythm of train travel will allow us to soak in the beauty of our surroundings and connect with fellow travelers.
As we approach our destination, the Twin Cities of Minneapolis and St. Paul emerge on the horizon. St. Paul, the state capital of Minnesota, boasts a rich history, vibrant arts scene, and beautiful parks along the Mississippi River. Whether you're eager to explore its cultural treasures or simply relax amidst its natural beauty, St. Paul offers a warm and welcoming experience.

Chicago to St. Paul

St. Paul

Get ready for an unforgettable adventure as we embark on an epic journey from the vibrant city of San Antonio to the bustling metropolis of Milwaukee. Along the way, we'll traverse diverse landscapes, encounter fascinating cultures, and create memories that will last a lifetime.
Our journey begins in the heart of the Lone Star State, where the vibrant colors and rich history of San Antonio await us. From exploring the historic missions to strolling along the River Walk, there's no shortage of wonders to discover. As we venture north, the scenery transforms into rolling hills and lush forests, painting a breathtaking panorama as we journey through the heart of America.
As we approach Milwaukee, the shores of Lake Michigan emerge, inviting us to soak in the stunning views. The vibrant city awaits our arrival, where a mix of art, music, and culture awaits. Prepare to be captivated by the charm of the Midwest, where the warmth of its people and the allure of its attractions will leave you enchanted.

San Antonio

San Antonio to Milwaukee

Traveler Resources

Get ready for an epic adventure as we embark on a journey from the bustling metropolis of Chicago to the picturesque town of Lakewood. Buckle up and prepare to witness a stunning transformation of landscapes, where towering skyscrapers give way to rolling hills and serene lakes. Along the way, we'll uncover hidden gems, marvel at natural wonders, and create memories that will last a lifetime. Whether you're a seasoned traveler or embarking on your first adventure, this trip promises an unforgettable experience filled with laughter, exploration, and endless discovery.
Our adventure will take us through diverse cities and charming towns, each with its unique character and allure. We'll immerse ourselves in the vibrant culture of Chicago, explore historic landmarks, and indulge in culinary delights. As we journey towards Lakewood, we'll encounter breathtaking natural landscapes, including majestic mountains, sparkling lakes, and lush forests. We'll embrace the great outdoors, hike through scenic trails, and capture postcard-worthy moments. Along the way, we'll meet friendly locals, learn about different cultures, and create connections that will enrich our understanding of the world.
Prepare to be captivated by the beauty of the Midwest as we uncover its hidden gems. We'll visit charming villages, explore historic sites, and savor the flavors of local cuisine. Each destination will offer a unique glimpse into the region's rich heritage, natural wonders, and vibrant communities. So, get ready to embark on a journey filled with wonder, discovery, and unforgettable moments that will inspire and ignite your imagination. The adventure from Chicago to Lakewood awaits, promising an extraordinary experience that will stay with you long after the journey ends.

Chicago to Lakewood

Lakewood

Get ready for an unforgettable adventure from the bustling streets of New York City to the charming city of Buffalo! Embark on a journey that will take you through picturesque landscapes, historic landmarks, and cultural treasures. This trip is a perfect blend of urban exploration and natural wonders, making it an ideal choice for families and travelers of all ages.
As you leave the vibrant streets of New York City behind, you'll embark on a scenic drive through the picturesque Hudson Valley. Rolling hills, lush forests, and charming towns will greet you along the way. The region is steeped in history, with numerous historic sites and landmarks waiting to be discovered. As you approach Buffalo, the landscape transforms into a captivating mix of urban and natural beauty.
Buffalo, a city nestled on the shores of Lake Erie, offers a vibrant blend of culture, history, and stunning waterfront views. Explore the city's fascinating museums, stroll through its charming neighborhoods, and indulge in its delectable cuisine. The trip concludes with a memorable visit to the iconic Niagara Falls, a majestic natural wonder that will leave you in awe. Witness the thunderous roar of the falls, feel the mist on your face, and capture breathtaking moments that will last a lifetime.

New York

New York to Buffalo

Buffalo

Get ready for an adventure, as we embark on a journey from the bustling metropolis of Chicago to the charming capital of Lansing. Our path takes us through picturesque landscapes, past serene lakes, and by vibrant cities. We'll witness the changing scenery as we traverse rolling hills and expansive farmlands. Whether you're a nature enthusiast, a history buff, or simply seeking a memorable road trip, this journey promises an unforgettable experience.
Along the way, we'll encounter historical landmarks that tell the story of Michigan's rich past. From iconic battlegrounds to stately courthouses, we'll delve into the events that shaped the state. We'll also discover hidden gems, tucked away from the beaten path, where local culture and traditions thrive. Each stop offers a unique glimpse into the heart and soul of Michigan.
As we approach our destination, Lansing welcomes us with open arms. The city exudes a blend of historic charm and modern amenities, creating a vibrant atmosphere. Whether you prefer exploring museums, attending festivals, or simply soaking up the local flavor, Lansing has something to offer every traveler. So fasten your seatbelts and get ready for an incredible journey that will create lasting memories.

Chicago to Lansing

Lansing

Get ready for an exciting adventure as we travel from the vibrant city of Detroit to the charming city of Milwaukee! Our journey will take us through picturesque landscapes, bustling towns, and along the sparkling waters of Lake Michigan. Along the way, we'll discover hidden gems, learn about the region's rich history, and create memories that will last a lifetime.
Our adventure begins in the heart of Detroit, where towering skyscrapers and bustling streets tell the story of a city on the rise. From here, we'll set out on our journey, winding our way through the rolling hills and lush forests of Michigan. As we cross the state line into Wisconsin, the scenery transforms into a tapestry of dairy farms and charming small towns. The vibrant colors of autumn leaves will paint the landscape in hues of gold, orange, and crimson, creating a breathtaking backdrop for our travels.
As we approach Milwaukee, the sparkling waters of Lake Michigan will come into view. The city's skyline, dotted with historic buildings and modern skyscrapers, will welcome us to our final destination. Milwaukee's rich German heritage is evident in its architecture, cuisine, and lively festivals, making it a perfect place to end our adventure and celebrate the journey we've shared.

Detroit

Detroit to Milwaukee

Events

Get ready for an unforgettable adventure as we embark on an epic road trip from the vibrant city of Austin to the charming town of Madison. Along the way, we'll traverse miles of breathtaking landscapes, discover hidden gems, and create memories that will last a lifetime. From the bustling streets of Austin to the serene shores of Lake Michigan, this journey will showcase the diverse beauty and rich history of the United States.
Our adventure begins in the heart of Texas, where Austin's vibrant culture and lively music scene set the tone for our journey. As we head north, we'll encounter rolling hills, lush forests, and charming towns that reveal the true essence of the Lone Star State. Leaving Texas behind, we'll cross the Red River into Oklahoma, where the vast prairies stretch out before us. The rich Native American heritage of this region is evident in the historic landmarks and cultural attractions that dot our path.
As we continue our journey through Kansas, we'll witness the iconic Flint Hills, a breathtaking landscape of rolling grasslands, and visit the Eisenhower Presidential Library and Museum in Abilene. Our adventure culminates in the charming town of Madison, nestled on the shores of Lake Michigan. Here, we'll soak in the beauty of the Midwest, explore the vibrant downtown area, and reflect on the incredible journey we've shared. Whether you're a seasoned traveler or embarking on your first road trip, this adventure promises to ignite your imagination and leave an everlasting impression.

Austin

Austin to Madison

Madison

Are you ready for an epic adventure? We're taking a road trip from the bustling streets of New York City to the vibrant city of Detroit! Along the way, we'll discover hidden gems, explore exciting cities, and create memories that will last a lifetime.
Our journey will take us through diverse landscapes, from sprawling farmlands to dense forests. We'll visit charming towns and bustling metropolises, each with its unique character and stories to tell. We'll embrace the vibrant culture, savor delicious local cuisine, and immerse ourselves in the rich history of the regions we pass through.
As we approach Detroit, the heart of the American automotive industry, we'll be greeted by a skyline dotted with iconic landmarks. We'll explore the city's rich musical heritage, visit its world-class museums, and discover the stories behind the innovations that have shaped our world. This road trip promises to be an unforgettable adventure, filled with discovery, laughter, and memories that will be cherished for years to come.

New York to Detroit

Hey, I found a trip that will take you on a breathtaking adventure. We'll travel along the shimmering shores of Lake Michigan, where the gentle waves whisper secrets to the sandy beaches. As we journey inland, lush forests will envelop us, their emerald canopies reaching towards the heavens like a living tapestry. Along the way, we'll encounter quaint towns and bustling cities, each with its own unique charm and story to tell. Whether you're an avid explorer or simply seeking a memorable escape, this trip promises an unforgettable experience.
As we approach the midway point of our journey, the landscape transforms into a vibrant tapestry of rolling hills and sparkling rivers. Picturesque farmsteads dot the horizon, their fields a patchwork of vibrant hues. The air fills with the sweet scent of wildflowers and the cheerful chorus of birdsong. We'll have ample opportunities to stretch our legs, breathe in the fresh air, and capture the beauty of our surroundings with our cameras.
Prepare to be captivated as we reach our final destination: a bustling city where history, culture, and modern amenities converge. Here, we'll explore fascinating museums, savor delectable cuisine, and immerse ourselves in the vibrant arts scene. This metropolis offers something for everyone, whether you seek adventure, relaxation, or intellectual stimulation. It's the perfect culmination to our extraordinary journey, leaving us with cherished memories and a newfound appreciation for the beauty and diversity of our surroundings.

Chicago to Kalamazoo

Kalamazoo

Hop aboard an exciting adventure as we embark on a journey that promises to captivate your senses. Escape the bustling city lights of Chicago and immerse yourself in the serene landscapes that unfold before you. Travel through a tapestry of vibrant countrysides, where rolling hills gracefully meet the horizon. Delight in the kaleidoscope of colors painted across the fields, a symphony of nature's artistry.
As you delve deeper into the heartland, the landscape transforms into a patchwork quilt of fertile farmlands. Marvel at the towering cornstalks standing as silent sentinels, their emerald blades swaying gently in the summer breeze. Witness the gentle grazing of cattle, their contented murmurs adding a tranquil melody to the rural symphony. Discover charming towns nestled amidst the countryside, each with its unique character and hidden gems waiting to be explored.
Conclude your journey in the vibrant city of Indianapolis, a melting pot of culture and history. Immerse yourself in the city's rich heritage as you explore its captivating museums and monuments. Discover its thriving arts scene, where creativity flourishes in every corner. Indulge in culinary delights at renowned restaurants, savoring the flavors of the Midwest. The city pulses with energy, offering a vibrant blend of urban sophistication and Midwestern charm, the perfect culmination to an unforgettable journey.