12 Best Ideas Family Road Trips from Chicago

Family Road Trips from Chicago can lead to scenic routes, theme parks, and historical sites. Discover the Midwest’s charm through adventures just hours away.

Embarking on a family road trip from Chicago opens the door to an array of memorable destinations. Whether seeking natural beauty, amusement for kids, or a touch of American history, the surrounding Midwest has it all. Drivers can find an array of attractions suitable for all ages within a few hours’ journey from the Windy City.

Ideal for weekend getaways or extended holidays, these trips promise engaging experiences that cater to various interests and budgets. Get ready to hit the road and create lasting impressions with your loved ones, exploring everything from the tranquil landscapes of Starved Rock State Park to the exhilarating rides of Six Flags Great America. Pack up the car, set your playlist, and drive into a tapestry of experiences that the heartland of America generously offers.

Table of Contents

Setting Off From Chicago Iconic Start To Your Journey

Chicago, the Windy City, is the perfect starting point for a family road trip. With its skyscraper-lined skyline and the glistening Lake Michigan beside it, setting off from Chicago isn’t just leaving a city—it’s leaving with a feeling of exhilaration.

Choosing Your Vehicle: Comfort Meets Utility

The right vehicle transforms a road trip from good to great. Comfort pairs with utility to create the perfect travel environment. Families need ample room for both passengers and luggage. Whether it’s a roomy SUV or a reliable minivan, the choice is critical for a smooth journey ahead.

  • Space for legs and fun.
  • Features like air conditioning and a good sound system.
  • Reliability to keep you moving without hiccups.

Packing Essentials: From Snacks To Soundtracks

Packing is an art, especially for a road trip. It’s not just throwing stuff in a bag. Essentials come first. They ensure a comfortable and enjoyable ride. With proper planning, you’ll have everything you need within reach.

Category Items
  • Healthy bites
  • Treats for fun
  • Favorite playlists
  • Audiobooks
  • Games
  • Pillows
  • Blankets
  • Chargers
  • First-aid kit

Don’t forget maps or a GPS app. Even in familiar territories, surprises can pop up.

Finally, curate a soundtrack to your adventure. Music is the backdrop of memory-making moments.

Weekend family road trips from Chicago

For families looking to embark on weekend road trips from Chicago, numerous destinations within a few hours’ drive offer fun and memorable experiences. Here are some family-friendly road trip ideas for weekends:

Wisconsin Dells, Wisconsin:

  • Approximate Driving Time: 3 hours
  • Known as the “Waterpark Capital of the World,” Wisconsin Dells offers a variety of indoor and outdoor water parks, amusement parks, and family-friendly attractions.
  • Families can enjoy thrilling rides and slides at parks like Noah’s Ark Waterpark, explore interactive attractions like Wizard Quest, and take scenic boat tours along the Wisconsin River.

Starved Rock State Park, Illinois:

  • Approximate Driving Time: 2 hours
  • Starved Rock State Park features towering sandstone bluffs, scenic waterfalls, and miles of hiking trails suitable for all ages.
  • Families can enjoy hiking to popular viewpoints like Starved Rock and Wildcat Canyon, have picnics in scenic areas, and participate in ranger-led programs and guided tours.

Galena, Illinois:

  • Approximate Driving Time: 3 hours
  • Galena is a historic town known for its charming downtown area, historic sites, and outdoor recreational opportunities.
  • Families can explore historic attractions like the Ulysses S. Grant Home and the Old Market House, take scenic drives along the Great River Road, and visit local shops and eateries.

Lake Geneva, Wisconsin:

  • Approximate Driving Time: 1.5 hours
  • Lake Geneva is a resort town known for its picturesque lakefront, outdoor activities, and family-friendly attractions.
  • Families can enjoy boating, swimming, and water sports on Geneva Lake, take scenic walks along the lakeshore path, and explore attractions like the Lake Geneva Cruise Line and Safari Lake Geneva.

Indiana Dunes National Park, Indiana:

  • Approximate Driving Time: 1.5 hours
  • Indiana Dunes National Park features scenic dunes, beaches, and hiking trails along the southern shore of Lake Michigan.
  • Families can enjoy swimming, sunbathing, and picnicking on the beach, hiking through dunes and forests, and participating in ranger-led programs and educational activities.

Grand Rapids, Michigan:

  • Approximate Driving Time: 3 hours
  • Grand Rapids offers a variety of family-friendly attractions, including museums, parks, and outdoor recreational opportunities.
  • Families can explore the John Ball Zoo, visit the Grand Rapids Children’s Museum, and spend time outdoors at Millennium Park or Frederik Meijer Gardens & Sculpture Park.

These are just a few weekend road trip ideas for families from Chicago, each offering a unique blend of attractions and activities suitable for all ages. Be sure to plan, book accommodations if necessary, and pack accordingly for a fun and stress-free getaway with your loved ones.

Illinois’ Hidden Gems Road Trip Routes

Exploring Illinois by car can be an adventure filled with surprises. Away from the hustle of Chicago, hidden routes lead to quaint towns, historic landmarks, and breathtaking landscapes. These paths offer unique experiences you might miss when sticking to the well-worn highways. Ready to discover the lesser-known jewels of Illinois? Jump into the family car and let these road trip routes guide you to the state’s hidden treasures.

Family Road Trips from Chicago to Historic Route 66

Embark on a journey through time along the legendary Historic Route 66. This iconic roadway begins in Chicago and carves a path southwest across Illinois. Here’s a snapshot of what you’ll discover:

  • The Launching Point: Visit the Route 66 Begin Sign at Adams Street, Chicago.
  • Muffler Men: Spot the quirky giants at various stops along the way.
  • The Cozy Dog Drive-In: Treat the family to a famous hot dog on a stick in Springfield.
  • The Gemini Giant: Snap a pic with the space explorer in Wilmington.

Every twist and turn on Route 66 reveals more of the rich history that has captivated road trippers for generations.

Family Road Trips from Chicago to The Great River Road

The Great River Road traces the mighty Mississippi and promises an unforgettable trip. Follow this scenic route to witness:

  1. Nature’s Beauty: See where the river rolls past lush landscapes and rugged cliffs.
  2. Eagle Watching: Spot America’s national bird soaring above or nesting in trees.
  3. Charming Towns: Explore river towns like Alton, with its rich Civil War history.
  4. Historic Sites: Visit the Cahokia Mounds State Historic Site, once home to ancient Native Americans.

With each mile along the Great River Road, families create memories beside America’s legendary river.

Family Road Trips from Chicago

Family Road Trips from Chicago to Wisconsin Bound

Escape the city bustle of Chicago for the serene landscapes of Wisconsin. Breathtaking colors and fresh, pine-scented air await on this northbound journey. Wisconsin’s natural beauty is unmatched, with its rolling hills, sparkling lakes, and quaint towns. It’s the perfect setting for memory-making family road trips.

Door County: The Cape Cod Of The Midwest

Door County beckons with its charming lighthouses and rustic cherry orchards. Known as the Cape Cod of the Midwest, this peninsula offers swap_Api_img of quaint shoreline. Discover quaint villages, artisanal shops, and outdoor recreation for the whole family.

  • Family-friendly beaches
  • Fresh local cherries and orchard tours
  • Scenic hiking trails in state parks

Wisconsin Dells: Waterparks And Wonderlands

Wisconsin Dells is a waterpark haven. With its title as the Waterpark Capital of the World, it’s a must-see destination. Exciting slides, lazy rivers, and giant wave pools promise endless fun for all ages.

Attraction Type Age Group
Noah’s Ark Waterpark Outdoor Waterpark All Ages
Kalahari Resorts Indoor/Outdoor Waterpark All Ages
Wisconsin Deer Park Wildlife Experience All Ages

In addition to waterparks, explore echoing caverns and riverboat tours. Wisconsin Dells delivers an unforgettable mix of adventure and relaxation.

Family Road Trips from Chicago

Family Road Trips from Chicago to Michigan’s Coastal Charm

Embarking on a family road trip from Chicago reveals the stunning vistas of Michigan’s coastline. Known for its endless blue waters and quaint beach towns, the Lake Michigan shoreline offers families an idyllic escape. This region combines natural beauty with historical charm, ensuring a journey full of memories. Get ready for a tour of Michigan’s most captivating coastal attractions.

Lake Michigan Shoreline: Sandy Escapes

Michigan’s shoreline is a treasure trove of sandy retreats. Imagine building sandcastles and splashing around in the fresh waters of Lake Michigan, under the warmth of the midwestern sun. Here are some must-visit beaches:

  • Silver Beach County Park: Ample space for picnics and a playground for kids.
  • Oval Beach: Known for powdery sand and clear waters.
  • Warren Dunes State Park: Dunes up to 260 feet high offer stunning views.
Mackinac Island: A Step Back in Time

Mackinac Island: A Step Back In Time

Mackinac Island is a portal to the past. Cars are absent on this island; bikes and horse-drawn carriages are the norm. Check out key spots:

Attraction Activity
Arch Rock: Natural limestone arch perfect for photos.
Fort Mackinac: Historic site with engaging reenactments.
Main Street: Boutique shopping and fudge tasting.

Relish the lack of modern hustle while taking in the Victorian architecture and the clip-clop of horses. This car-free paradise allows kids to roam free and imagine life in a different era.

Indiana's Lakes Family Road Trips from Chicago

Family Road Trips from Chicago to Indiana’s Lakes And Parks

Embark on a journey from Chicago to the stunning landscapes of Indiana. Here, refreshing lakes and picturesque parks await families seeking fun and relaxation. En route to these natural havens, every moment promises to become a cherished memory.

Indiana Dunes: Adventures On The Shore

Indiana Dunes National Park offers sandy adventures just a short drive from Chicago. The park boasts over 15,000 acres of dunes, forests, and wetlands. Find yourself immersed in activities such as:

  • Swimming and sunbathing on over 15 miles of sandy shores.
  • Hiking diverse trails that accommodate all skill levels.
  • Observing rare bird species in their natural habitat.

Don’t miss the dramatic sunsets over Lake Michigan, perfect for family photos that last a lifetime.

Brown County: Art And Autumn Leaves

Venture further into Indiana to discover Brown County State Park, known as the “Little Smokies”. Its lush hills and vibrant fall foliage will captivate both art lovers and nature enthusiasts.

  • Explore the art galleries nestled in the heart of Brown County.
  • Bask in the autumn glow on scenic drives through the park.
  • Engage in outdoor activities such as horseback riding and biking.

With family-focused events throughout the year, Brown County merges nature’s beauty with cultural flair.

Family Road Trips from Chicago: Scenic Getaways Unveiled!

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Family Road Trips from Chicago to Iowa’s Rolling Hills And Historic Towns

Embark on a delightful journey through Iowa’s scenic landscapes and charming historic towns. Chicago families often seek nearby escapes that offer both tranquility and a touch of cultural enrichment. Iowa, with its undulating hills and rich history, presents the perfect backdrop for these adventures.

Amana Colonies: German Culture And Crafts

The Amana Colonies beckon with a warm invitation to discover German heritage. Looming over the rural Iowa scene, these seven villages offer a window into a unique past. Artisanal crafts, homemade foods, and quaint shops stand as testaments to the industrious spirit of the communities’ German settlers.

  • Handcrafted furniture and woolens
  • Authentic German restaurants and bakeries
  • Engaging festivals throughout the year

Loess Hills: Unique Landscapes And Vineyards

In western Iowa, the Loess Hills rise majestically, offering a spectacular natural phenomenon. Unlike any other terrain, these hills are sculpted by windswept soils and support a rich biodiversity. Family road-trippers can relish panoramic views and discover hidden gems.

Local vineyards dot the landscape, inviting you to savor Iowa’s homegrown wines. Each stop presents crisp tastes and family-owned hospitality.

Activity Description Location
Hiking Explore trails with breathtaking vistas. State Parks
Wine Tasting Sample fine wines in picturesque settings. Local Vineyards

Family Road Trips from Chicago to Missouri’s Cultural Crossroads

Embark on an adventure from Chicago to Missouri. Experience the blend of city vibes and countryside charm. Missouri’s cultural crossroads beckon families with open arms. Discover history, enjoy live entertainment, and unwind amid nature.

St. Louis Gateway: Beyond The Arch

St. Louis, famously known for its majestic Gateway Arch, offers much more. Dive into the city’s rich history at the Museum of Westward Expansion. Kids love the City Museum with its enchanted caves and sky-high slides. Don’t miss the Saint Louis Zoo, a thrilling day out for the whole family.

  • Forest Park — A Hit with Nature Lovers
  • The Magic House — Hands-on Fun for Kids
  • Botanical Gardens — A Botanical Paradise

Branson: Live Shows And Leisure

Branson is a treasure trove of family fun. Dazzling live shows light up the evenings. The 76 Country Boulevard is lined with entertainment spots. Heat up with daytime adventures at the Silver Dollar City theme park. Cool down at the Table Rock Lake with a splash.

Branson Highlights
Attraction Activity Type
Titanic Museum Historical Exploration
Dolly Parton’s Stampede Dinner Show
Branson Ferris Wheel Scenic Views
Family Road Trips from Chicago

Family Road Trips from Chicago to Kentucky’s Bluegrass Country

Escape the Windy City and dive into Kentucky’s Bluegrass Country. Families love these adventures. Rolling hills and horse farms welcome you to a place of Southern charm. Your trip will be full of wonder and tastes. Ready for the ride?

Bourbon Trail: Taste And Tour

Begin a delicious journey on the Bourbon Trail. Kids can enjoy sweet treats while parents sample Kentucky’s legacy. Here’s what to expect:

  • Guided Tours: Learn how bourbon is made.
  • Scenic Stops: Snap photos at famous distilleries.
  • Tasting Sessions: Savor different bourbon varieties.

Plan your visits ahead. Distilleries often require reservations.

Mammoth Cave: Exploring Underground Wonders

Mammoth Cave is a must-see. It’s the world’s longest-known cave system! Explore its beauty:

  1. Fascinating Tours: Choose easy or adventurous paths.
  2. Educational Activities: Kids learn about geology and history.
  3. Incredible Formations: Gaze at stalactites and stalagmites.

Remember to bring comfortable shoes. The cave’s wonders await your footsteps.

Family Road Trips from Chicago to Melodies And Mountains

Embark on a melody-filled mountain adventure beginning from Chicago, whisking your family to the musical heart of Tennessee. Discover how the land of the Great Smoky Mountains blends perfectly with the vibrant country music scenes to offer an unforgettable road trip experience.

Nashville: Country Music’s Home

Nashville isn’t just a city; it’s country music’s playground. Here, melodies flow like the Cumberland River, touching the soul of every visitor.

  • Grand Ole Opry: Stand where legends stood and absorb the history.
  • Country Music Hall of Fame: Immerse in the stories and sounds that shaped a genre.
  • Ryman Auditorium: Feel the vibrations of music’s past and present.

Strum through the Honky Tonks on Broadway for live shows that will make you stomp and cheer.

Smoky Mountains: Nature’s Splendor

The Smoky Mountains beckon with their infinite beauty and outdoor activities. This natural playground is perfect for family bonding.

Attraction Activity
Cades Cove Wildlife spotting, historic sites
Clingmans Dome Panoramic views, hiking trails
Ober Gatlinburg Amusement park, ski area

Explore scenic drives, hiking trails, and captivating waterfalls for memorable moments. Breathe in the fresh mountain air and let nature’s splendor envelop you.

Family Road Trips from Chicago: Scenic Getaways Unveiled!

Credit: www.travelweekly.com

The Allure Of The Starved Rock State Park

The Allure of the Starved Rock State Park lies in its unspoiled beauty.
A treasure trove of scenic wonders, the park beckons families for an unforgettable road trip.
Just a drive from Chicago, this natural gem offers a break from city life.
Its rugged canyons, cascading waterfalls, and lush forests are perfect for exploration.

Waterfall Chasing: Seasonal Beauty

The quest for waterfalls at Starved Rock State Park is best in spring or after heavy rains.
Waterfalls transform the park into a magical landscape.
Pack a picnic and watch the water dance at Wildcat, LaSalle, or St. Louis Falls.
The waterfalls offer stunning photo opportunities and refreshing hikes for all.

Hiking Trails: Find Your Perfect Path

Over 13 miles of trails await at Starved Rock.
Choose an easy, family-friendly path, or challenge yourself with rugged terrain.
Trails like Lover’s Leap and Eagle Cliff offer panoramic views.
Remember to carry a map and wear comfortable shoes for a day full of adventure.

Keeping Kids Engaged On The Drive

Families embarking on a road trip from Chicago face a common challenge: keeping kids entertained. A long drive can turn tedious for young passengers. Yet, with creativity and planning, the journey becomes part of the adventure. Here’s how to ensure smiles all around, even during the longest stretches of your road trip.

Entertainment Packs: Technology And Toys

Build excitement with personalized entertainment packs for each child. Fill these packs with a mix of tech gadgets and traditional toys. The key is variety.

  • Tablets or portable DVD players pre-loaded with movies and games
  • Headphones to allow each child to enjoy their media
  • A selection of favorite books and comic books
  • Puzzle books and coloring supplies for a creative outlet
  • Small toys and action figures for imaginative play

Remember to include chargers and possibly a car charger adapter to keep devices powered up. Rotate toys to keep interest high during the journey.

Interactive Games: Engaging The Whole Family

Interactive games unite the family, turning drive time into fun time. Here’s a list of activities that involve everyone:

  1. “I Spy” – Perfect for drivers and passengers alike
  2. The License Plate Game – Find as many different states as possible
  3. Travel bingo – Spot items on your card as you drive
  4. Storytelling rounds – Each person adds a sentence to build a story
  5. 20 Questions – Guess the object one person is thinking of

Choose games that require minimal supplies to save space. These games trigger laughter and create memorable trip moments. Engage in these games regularly to keep energy levels high and boredom at bay.

Returning Home: Cherishing Memories

After an exhilarating road trip full of laughter and discoveries,
coming home to Chicago brings a comforting end to an incredible journey.
Your spirit is full, your heart content, but there’s a longing to hold onto those
moments. Fortunately, cherishing road trip memories is a joy in itself.

Photo Albums: Preserving The Moments

Turning digital snapshots into physical photo albums is an intimate way to
preserve your favorite moments. A picture can truly speak a thousand words. Each
printed photo tells a story, evoking the smells, sounds, and feelings of the
road once more.

  • Select your favorite photos, perhaps of a scenic sunset or a family meal.
  • Compile them in a beautiful album, with notes on each page.
  • Relive the adventure whenever you flip through these personal treasures.

Sharing Your Adventure: Blogs And Social Media

Blogs and social media offer a vibrant canvas to share your family’s escapades.
A blog post with narratives and eye-catching images engages friends and fellow travel
enthusiasts alike.

Platform Use For
Blog Detailed storytelling and photo journals
Instagram Visual snippets and fun reels
Facebook Albums and status updates to family
Twitter Quick snippets and highlights

Remember, capturing the essence of your experiences with heartfelt captions
adds a personal touch that resonates with your circle and beyond. Start a conversation,
engage with comments, and create connections over shared experiences.

Family Road Trips from Chicago: Scenic Getaways Unveiled!

Credit: www.amazon.com

Frequently Asked Questions For Family Road Trips From Chicago

What Are Top Family Destinations Near Chicago?

Chicago families enjoy a variety of nearby destinations. Starved Rock State Park offers hiking and lovely views. The Wisconsin Dells presents waterparks and amusements. Lake Geneva provides a relaxing lakeside retreat suitable for all ages.

How Long Is A Road Trip To Starved Rock?

Starved Rock State Park is about 94 miles from Chicago. Typically, it takes around 1 hour and 45 minutes to reach by car, making it an excellent choice for a day trip or a weekend getaway with the family.

Are There Kid-Friendly Activities In Wisconsin Dells?

Yes, Wisconsin Dells is packed with kid-friendly activities. Renowned for its waterparks, there are also theme parks, boat tours, and interactive exhibits. It’s a prime destination for families looking to have fun.

What’s The Best Time To Visit Lake Geneva?

The best time to visit Lake Geneva is during the summer. The warmer months offer outdoor activities such as boating, fishing, and hiking. Autumn also attracts visitors with its vibrant foliage, making it an ideal spot year-round.


Embarking on a road trip from Chicago with your loved ones can offer unforgettable experiences and bonding moments. Each route promises its own set of adventures and sights. So pack your snacks, queue up your playlist, and hit the road—the Midwest is waiting to share its treasures with your family.

Safe travels!

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