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Friday, July 12, 2024

Best Road Trips From Chicago – Explore The Midwest And Beyond

Embarking on a journey from the heart of the Midwest, Chicago, opens up a world of road trip possibilities that go beyond the city’s towering skyline. Whether you’re a history enthusiast, nature lover, or simply seeking a change of scenery, the roads that sprawl out from Chicago offer a myriad of adventures waiting to be explored.

Picture yourself cruising down the iconic Route 66, the wind in your hair as you pass by quirky landmarks and classic diners. Feel the serenity of a lakeside escape on the route from Chicago to Door County, Wisconsin, where charming towns and scenic views of Lake Michigan await. Perhaps you’re drawn to the rich flavors of whiskey – in that case, the Kentucky Bourbon Trail beckons with its distillery tours and cultural immersion.

Top 10 Best Road Trips from Chicago 

Embarking on a road trip from Chicago unveils a treasure trove of diverse landscapes, cultural experiences, and hidden gems. Here, we present the top 10 best road trips from the Windy City, each offering a unique adventure for every type of traveler.

1. Historic Route 66 Expedition:

Kickstart your road trip by tracing the iconic Route 66, a historic highway that takes you through charming towns, quirky roadside attractions, and the heartland of America. Dive into the nostalgia of classic diners and motels along the way.

2. Lakeside Serenity to Door County:

Head north for a lakeside escape to Door County, Wisconsin. This scenic drive along Lake Michigan unveils picturesque landscapes, lighthouses, and outdoor activities. Discover the charm of quaint towns and savor local delights.

3. Bourbon Trail Excursion to Kentucky:

For whiskey enthusiasts, a journey to the Kentucky Bourbon Trail is a must. Immerse yourself in the world of bourbon with distillery tours, tastings, and a glimpse into the rich cultural heritage of Kentucky.

4. Nature Retreat at Starved Rock State Park:

Find tranquility in nature at Starved Rock State Park, just a few hours from Chicago. Hike through lush trails, witness breathtaking waterfalls, and embrace the serenity of the great outdoors. Ideal for a weekend retreat.

5. Urban Escape to Milwaukee:

Experience the vibrant city life of Milwaukee, a short drive from Chicago. Explore cultural attractions, breweries, and the scenic Lake Michigan waterfront. Perfect for a day trip or a weekend getaway.

6. Crossing Borders to Toronto:

Expand your horizons by driving north to Toronto, Canada. Encounter diverse cultures, iconic landmarks, and a culinary scene that reflects the city’s multicultural vibe. Don’t forget to plan for the border crossing.

7. Rustic Charm of Galena:

Step back in time in the historic town of Galena, Illinois. Wander through antique shops, stroll along charming streets, and explore the town’s rich history. Enjoy local cuisine and cozy accommodations.

8. Great River Road to Dubuque:

Follow the Great River Road south to Dubuque, Iowa, and be captivated by the scenic beauty along the Mississippi River. Discover river towns, historic sites, and recreational activities along this picturesque route.

9. Majestic Dunes of Indiana:

Head west to Indiana Dunes National Park for a mix of sandy shores, rolling dunes, and diverse ecosystems. Hike the trails, relax on the beach, and witness stunning views of Lake Michigan.

10. Gateway to the West – St. Louis, Missouri:

Journey southwest to St. Louis for a taste of Midwestern hospitality. Explore the iconic Gateway Arch, stroll along the historic riverfront, and indulge in the city’s culinary delights.

Planning Tips for a Perfect Road Trip

Embarking on a road trip is an exhilarating adventure, but proper planning is the key to ensuring a seamless and enjoyable journey. Whether you’re hitting the open road for a weekend getaway or an extended expedition, these planning tips will help you make the most of your road trip:

Define Your Route:

Before you hit the road, plan your route. Consider scenic detours, interesting landmarks, and attractions along the way. Utilize navigation apps to find the best routes and real-time traffic updates.

Vehicle Check:

Ensure your vehicle is road-trip ready. Check the oil, brakes, tires, and fluid levels. Don’t forget the spare tire and tools for emergencies. A well-maintained car minimizes the risk of breakdowns.

Packing Essentials:

Pack wisely. Consider the climate, activities planned, and the duration of your trip. Essentials include clothing, toiletries, chargers, snacks, and any necessary medications. Create a checklist to avoid overlooking items.

Entertainment and Navigation:

Load up on road trip playlists, podcasts, and audiobooks to keep everyone entertained. Bring physical maps or a GPS device, even if you rely on smartphone apps, to ensure you’re connected even in areas with poor signal.

Accommodation Reservations:

If your road trip involves overnight stays, book accommodations in advance. This ensures you have a place to rest, especially during peak travel times or in popular tourist destinations.

Budget Planning:

Create a budget for your road trip, including fuel, accommodation, meals, and activities. Having a rough estimate helps you manage expenses and avoid overspending.

Flexible Itinerary:

While planning is crucial, leave room for spontaneity. Be open to detours and unexpected discoveries. Some of the best road trip memories come from unplanned stops and hidden gems.

Snacks and Hydration:

Stock up on water and non-perishable snacks. This not only keeps you energized but also saves time and money on frequent stops. Consider a cooler for perishable items.

Safety First:

Prioritize safety. Carry a first aid kit, roadside emergency tools, and a flashlight. Let someone know your itinerary, and check-in periodically if possible. Familiarize yourself with local emergency services along your route.

Travel Insurance:

Consider travel insurance that covers road trips. It provides peace of mind in case of unforeseen events, such as accidents, medical emergencies, or trip cancellations.

Environmental Considerations:

Be mindful of eco-friendly practices. Minimize single-use plastic, dispose of waste responsibly, and choose eco-friendly accommodations when possible.

Camera and Documentation:

Bring a camera to capture memories, and ensure you have all necessary documentation, including your driver’s license, registration, and insurance.


As the journey comes to a close, the road trips from Chicago unfold as diverse chapters in a travelogue of exploration and discovery. From the iconic stretches of Route 66 to the serene landscapes of Door County, Wisconsin, each adventure offers a unique tapestry of experiences.

Whether you find solace in the natural beauty of Starved Rock State Park, embrace the cultural vibrancy of Milwaukee, or cross borders to explore the cosmopolitan allure of Toronto, the road trips emanating from Chicago present a mosaic of possibilities for every traveler.

Galena’s rustic charm, the bourbon-soaked trails of Kentucky, and the urban escape to Saugatuck offer glimpses into the multifaceted nature of these excursions. As you traverse the Great River Road or venture to the Ozarks, the memories forged along the way become the essence of these road trips.

This guide aimed to be a compass, directing you through the highways and byways that extend from the Windy City. The joy of the open road lies not just in the destinations but in the journey itself – the unexpected turns, scenic vistas, and the freedom to explore. As you reflect on the adventures from Chicago, may these road trips linger in your memories, inspiring future escapades and kindling the spirit of wanderlust.

Shamim Ahmed
Shamim Ahmed
Shamim Ahmed is a certified professional news writer who is also experienced in the travel and sports sectors. He embarked upon a career as a writer and editor. He always appears to us with the latest news which is his passion. Not only that, he helps people to raise their voices for their rights. He also enjoys writing about sports and travels and has contributed to various sports sites. He is a strong believer that the right words can educate and simplify. He loves writing about technical/complex details in a simple, easy-to-understand, digestible, friendly way.


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