Get ready for an adventure of a lifetime! We'll embark on a thrilling journey from the bustling metropolis of Chicago to the vibrant border town of Brownsville. Along the way, we'll traverse diverse landscapes, encounter fascinating cultures, and create memories that will last a lifetime.
Our adventure begins in the heart of Chicago, a city known for its iconic skyline, world-class museums, and bustling streets. From there, we'll wind our way through the picturesque Midwest, passing by rolling hills, charming towns, and vast farmlands. As we approach the southern border, the landscape transforms into a vibrant tapestry of deserts, mountains, and coastal plains.
Throughout our journey, we'll have the opportunity to immerse ourselves in the local culture. We'll visit historic sites, savor delicious regional cuisine, and interact with friendly locals who will share stories of their lives and traditions. The journey from Chicago to Brownsville promises to be an unforgettable experience, filled with adventure, discovery, and a profound appreciation for the diversity of our nation.

Chicago

Chicago to Brownsville

Outdoor Activities

Nature & Parks

Shopping

Spas & Wellness

Fun & Games

Sights & Landmarks

Museums

Traveler Resources

Concerts & Shows

Water & Amusement Parks

Nightlife

Tours

Other

Brownsville

Chicago to Winter Haven

Winter Haven

Get ready for an exciting adventure as we embark on a journey from the bustling metropolis of Chicago to the charming city of Davenport, nestled along the banks of the mighty Mississippi River. Along the way, we'll traverse scenic landscapes, marvel at architectural wonders, and discover hidden gems waiting to be explored. From the vibrant streets of Chicago to the tranquil riverfront of Davenport, each mile holds endless possibilities for adventure and discovery.
As we leave the towering skyscrapers and vibrant energy of Chicago behind, we'll embark on a picturesque drive through the rolling countryside. Verdant fields stretch out before us, dotted with quaint farmhouses and whispering willow trees. Quaint towns and villages invite us to stop and explore their unique charm, each with its own story to tell. As we approach Davenport, the landscape transforms, and the riverfront beckons us with its tranquil beauty.
Our destination, Davenport, welcomes us with open arms. This historic city boasts a rich heritage, evident in its beautifully preserved architecture and vibrant arts scene. Along the Mississippi Riverfront, we'll stroll amidst towering bluffs and lush parks, soaking in the breathtaking views. Davenport's charming downtown invites us to wander its cobblestone streets, browse unique boutiques, and savor delicious cuisine. Whether you seek adventure, history, or simply the joy of exploration, this journey from Chicago to Davenport promises an unforgettable experience filled with wonder and discovery.

Chicago to Davenport

Casinos & Gambling

Classes & Workshops

Davenport

Prepare yourself for an epic adventure as we embark on an unforgettable road trip from the bustling metropolis of Chicago to the sun-kissed shores of Palm Coast. Along the way, we'll traverse diverse landscapes, from towering skyscrapers to rolling hills and sparkling lakes. Adventure awaits as we discover hidden gems, marvel at awe-inspiring sights, and create memories that will last a lifetime.
As we leave the Windy City behind, we'll venture into the heartland of America, passing through charming small towns and serene countryside. We'll stop at roadside attractions, explore quaint villages, and take in the beauty of nature's wonders. As we approach our destination, the sun will begin to dip, casting a golden glow over the landscape. We'll arrive in Palm Coast just as the stars twinkle above, ready to embrace the tranquility and warmth of our coastal haven.
This road trip promises an abundance of opportunities to learn, grow, and bond as a family. From visiting museums and historical landmarks to splashing in the ocean and building sandcastles, there's something for everyone to enjoy. Embrace the adventure, let your imaginations soar, and create unforgettable moments that will be cherished for years to come.

Chicago to Palm Coast

Palm Coast

Chicago to Norwich

Food & Drink

Norwich

Take a break from the hustle and bustle of Los Angeles and embark on an adventure to the charming city of Rockford. This cross-country journey promises a memorable experience filled with diverse landscapes, rich history, and endless opportunities for exploration.
As you leave the City of Angels behind, the sprawling metropolis gives way to picturesque valleys, rolling hills, and vast deserts. Embrace the ever-changing scenery as you traverse the heartland of America, discovering hidden gems and immersing yourself in the local culture along the way.
Upon arriving in Rockford, you'll be greeted by a vibrant community rooted in industry and innovation. Explore the city's rich heritage at the Midway Village Museum Center, where you can step back in time and experience life as it was in the 19th century. Indulge in the arts at the Rockford Art Museum, showcasing a diverse collection of contemporary and historical works. Immerse yourself in the beauty of nature at the Anderson Japanese Gardens, a tranquil oasis inspired by traditional Japanese design.

Los Angeles

Los Angeles to Rockford

Rockford

Prepare yourself for an unforgettable road trip from the bustling metropolis of Chicago to the sun-drenched city of Fresno. Along this epic journey, you'll traverse diverse landscapes, from the rolling hills of the Midwest to the majestic mountains of the West. Embrace the freedom of the open road and embark on a captivating adventure filled with countless wonders.
Witness the transformation of the landscape as you leave behind the towering skyscrapers of Chicago and enter the serene embrace of Iowa's cornfields. Admire the picturesque charm of small towns and marvel at the vast expanse of the Nebraska plains. As you approach the Rocky Mountains, the scenery becomes breathtaking, with towering peaks piercing the sky and sparkling rivers meandering through lush valleys.
Finally, as you reach the outskirts of Fresno, the air fills with the sweet scent of orange groves and blooming vineyards. The journey culminates in the vibrant heart of the San Joaquin Valley, where endless sunshine and warm hospitality await you. Prepare to be captivated by the diverse cultures, stunning natural beauty, and endless possibilities that await you along this extraordinary road trip.

Chicago to Fresno

Fresno

Get ready for an unforgettable adventure as we embark on a thrilling journey from the bustling city of Chicago to the charming town of Hartford. Along the way, we'll traverse vast landscapes, marvel at iconic landmarks, and create memories that will last a lifetime.
Our adventure begins in the heart of the Windy City, where skyscrapers pierce the sky and the vibrant streets hum with life. From here, we'll set off on a path that leads us through rolling hills, serene lakes, and picturesque countryside. As we travel, we'll encounter friendly locals, discover hidden gems, and immerse ourselves in the rich history and culture of the region.
As we approach our destination, the landscape transforms into a tapestry of lush forests, sparkling rivers, and quaint towns. Hartford, with its historic charm and modern amenities, welcomes us with open arms. Once there, we'll explore its museums, stroll through its parks, and savor the flavors of its culinary delights. The journey from Chicago to Hartford is not merely a trip; it's an adventure filled with discovery, wonder, and the creation of cherished memories.

Chicago to Hartford

Hartford

Are you ready to embark on an epic adventure? Our exciting journey will take us from the bustling streets of Chicago to the sunny shores of Sunnyvale. Along the way, we'll discover hidden gems, make memories that will last a lifetime, and experience the beauty and diversity of our country.
As we leave the Windy City behind, we'll venture into the heartland of America, passing through charming towns and rolling hills. We'll embrace the spirit of exploration as we encounter friendly locals, learn about different cultures, and immerse ourselves in the vibrant history of our nation. As the miles turn into memories, we'll share laughter, stories, and create bonds that will connect us long after our journey ends.
Finally, as we approach our destination, the California sunshine will greet us warmly, inviting us to bask in its golden rays. Sunnyvale awaits with open arms, ready to share its own unique blend of culture, innovation, and natural beauty. Whether we're exploring the vibrant tech scene, marveling at the redwoods, or simply enjoying the laid-back coastal lifestyle, Sunnyvale promises an unforgettable finale to our cross-country adventure. So buckle up and get ready for the ride of a lifetime!

Chicago to Sunnyvale

Sunnyvale

Miami

Miami to Champaign

Champaign

Get ready for an unforgettable journey from the bustling metropolis of Chicago to the vibrant heart of Silicon Valley, San Jose! This epic adventure will take you through diverse landscapes, from the shores of Lake Michigan to the rolling hills of California. Along the way, you'll encounter iconic cities, historical landmarks, and breathtaking natural wonders. Embrace the spirit of exploration as you uncover the hidden gems and rich tapestry of American culture that unfolds before your eyes on this captivating cross-country voyage.
Prepare to be mesmerized by the urban energy of Chicago, a city known for its towering skyscrapers, world-class museums, and vibrant arts scene. Immerse yourself in the Windy City's charm before embarking on your westward journey. As you traverse the vast expanse of the country, marvel at the ever-changing scenery. Witness the serene beauty of the Great Plains, the rugged grandeur of the Rocky Mountains, and the lush greenery of the Pacific Northwest. Each mile traveled will bring you closer to the innovation hub of San Jose, a city brimming with technological advancements and a thriving cultural scene.
Upon arriving in San Jose, embrace the vibrant energy of Silicon Valley, where dreams are born and the future is shaped. Explore the cutting-edge tech companies, delve into interactive museums, and soak up the infectious enthusiasm that drives this region. San Jose offers a harmonious blend of urban sophistication and natural beauty, with its proximity to stunning beaches, redwood forests, and majestic mountains. Let the spirit of discovery guide you as you uncover the countless wonders that await you on this extraordinary journey from Chicago to San Jose.

Chicago to San Jose

San Jose

Get ready for an unforgettable adventure as we embark on an epic road trip from the bustling city of Chicago to the vibrant heart of Lubbock, Texas! This incredible journey will traverse diverse landscapes, from towering skyscrapers to rolling hills, passing through iconic landmarks and hidden gems along the way.
As we leave the Windy City behind, the urban sprawl gradually gives way to serene countryside vistas. The open road stretches out before us, inviting exploration and discovery. Miles turn into memories as we witness the ever-changing scenery, from lush forests and sparkling lakes to charming small towns and historic sites.
This grand odyssey is a symphony of adventure, history, and cultural immersion. We'll encounter friendly locals, savor delicious regional cuisine, and learn about the rich heritage of the American heartland. From the bustling metropolises to the tranquil countryside, every mile holds a new adventure, waiting to be experienced and cherished.

Chicago to Lubbock

Lubbock

We're excited to announce our upcoming trip from Detroit to Bloomington! This thrilling adventure will take us through a diverse and captivating landscape, promising an unforgettable experience. Get ready to marvel at the wonders of nature, explore vibrant cities, and create memories that will last a lifetime.
Along the way, we'll discover hidden gems and iconic landmarks, immersing ourselves in the rich tapestry of culture and history that defines this region. From bustling metropolises to serene countryside escapes, every destination promises a unique charm and unforgettable encounters. We'll encounter friendly locals, savor delicious cuisine, and uncover the stories that have shaped this incredible part of the world.
As we journey from Detroit to Bloomington, we'll traverse rolling hills, lush forests, and sparkling waterways, each offering a breathtaking canvas for nature's artistry. We'll feel the pulse of vibrant cities, where towering skyscrapers and bustling streets tell tales of progress and innovation. And we'll retreat to tranquil havens, where nature's symphony soothes the soul and invites us to connect with the wonders of the natural world.

Detroit

Detroit to Bloomington

Bloomington

Chicago to Tallahassee

Boat Tours & Water Sports

Tallahassee

Hop aboard and get ready to explore the vibrant landscapes and hidden gems that lie between the bustling city of Waukegan and the charming town of Waukesha. Embark on a journey that weaves through rolling hills, meandering rivers and picturesque countryside, where every turn promises a new adventure.
Discover the rich heritage and cultural tapestry that unfolds along the way. Immerse yourself in the captivating stories and traditions that have shaped this region, from the vibrant arts scene to the thriving culinary landscape. Meet the friendly locals who are eager to share their unique perspectives and create lasting memories.
Indulge in the natural beauty that surrounds you. Take a leisurely stroll through lush parks, marvel at breathtaking vistas from scenic lookouts, and uncover the secrets of hidden waterfalls. Whether you seek tranquility in nature or the excitement of urban exploration, this journey offers an unforgettable blend of experiences that will ignite your senses and leave you longing for more.

Waukegan

Waukegan to Waukesha

Waukesha