Chicago, known for its iconic skyline, deep-dish pizza, and rich cultural history, might not be the first place that comes to mind when you think of overlanding. However, for those who crave adventure and the great outdoors, the city and its surroundings offer a surprising array of overlanding opportunities. Whether you’re a seasoned overlander with a fully equipped Jeep or a novice looking to explore new terrains, Chicago’s diverse landscapes provide an excellent backdrop for your journey.

What is Overlanding?
Before diving into the specifics of overlanding in Chicago, it’s essential to understand what overlanding entails. Overlanding is a self-reliant, vehicle-dependent travel to remote destinations where the journey is as important as the destination. It combines off-road driving with camping, allowing travelers to explore less-traveled paths and immerse themselves in nature.
Preparing for Your Overlanding Trip
Choosing the Right Vehicle
For overlanding, having a reliable vehicle is crucial. Many enthusiasts prefer 4WD vehicles like Jeeps, which are well-suited for navigating rugged terrains. Your vehicle should be equipped with essential gear, including:
- Off-road tires: These provide better traction and durability on uneven surfaces.
- Recovery gear: Items such as tow straps, a winch, and a shovel can be lifesavers if you get stuck.
- Navigation tools: A GPS device and detailed maps are vital for staying on track in remote areas.
- Camping equipment: A rooftop tent, sleeping bags, and cooking gear ensure you can comfortably camp wherever you find yourself.
Essential Gear and Supplies
Overlanding requires more than just a capable vehicle. Ensure you pack:
- Food and water: Carry enough supplies for the duration of your trip, plus extra in case of emergencies.
- First aid kit: Be prepared for minor injuries with a comprehensive first aid kit.
- Clothing: Pack layers to accommodate varying weather conditions.
- Communication devices: A satellite phone or two-way radio can be crucial in areas with no cell service.
Best Overlanding Routes Near Chicago
The Driftless Area
Located in southwestern Wisconsin, the Driftless Area is a perfect overlanding destination near Chicago. Known for its unique terrain, untouched by glaciers, this region offers rolling hills, deep river valleys, and scenic backroads.
- Route highlights: Start your journey in Chicago and head northwest towards the Driftless Area. Explore the winding roads along the Mississippi River, stop at small towns like Galena, IL, and Prairie du Chien, WI, and camp in one of the many state parks.
- Points of interest: Mississippi Palisades State Park, Kickapoo Valley Reserve, and Wildcat Mountain State Park.
Shawnee National Forest
Located in southern Illinois, Shawnee National Forest is another excellent destination for overlanders. This vast forest area features diverse ecosystems, from lush woodlands to rocky bluffs.
- Route highlights: Drive south from Chicago, passing through the charming towns of central Illinois. Once you reach Shawnee National Forest, explore the scenic byways and off-road trails.
- Points of interest: Garden of the Gods, Little Grand Canyon, and the Ohio River Scenic Byway.
Michigan’s Upper Peninsula
For those willing to venture a bit farther, Michigan’s Upper Peninsula (UP) offers some of the best overlanding experiences in the Midwest. Known for its remote wilderness and pristine landscapes, the UP is a haven for outdoor enthusiasts.
- Route highlights: Head northeast from Chicago, cross into Michigan, and make your way to the UP. Explore the Keweenaw Peninsula, Porcupine Mountains, and the vast network of forest roads and trails.
- Points of interest: Pictured Rocks National Lakeshore, Copper Harbor, and Tahquamenon Falls State Park.
Overlanding Community and Resources
Connecting with Fellow Overlanders
Chicago has a vibrant overlanding community. Joining local groups and forums can provide valuable insights, trip ideas, and companionship. One such resource is the 4WD Talk Jeep Forum, where you can connect with fellow overlanders, share experiences, and seek advice.
Overlanding Events and Meetups
Attending overlanding events and meetups is a great way to learn more about the hobby and meet like-minded individuals. Events such as Overland Expo and local off-road clubs often host gatherings, workshops, and trail rides in the Midwest.
Safety Tips for Overlanding in Chicago
Weather Considerations
The Midwest’s weather can be unpredictable, so it’s essential to be prepared for all conditions. Monitor the weather forecast before and during your trip, and be ready for sudden changes, especially in remote areas where shelter may be limited.
Wildlife and Natural Hazards
While overlanding in the Midwest, you may encounter various wildlife, from deer to black bears. Understanding how to safely interact with wildlife and securing your food and trash can help avoid unwanted encounters. Additionally, be aware of natural hazards such as flooding rivers or fallen trees, which can obstruct trails.
Emergency Preparedness
Being prepared for emergencies is vital. Always inform someone of your travel plans, including your route and expected return date. Carry a well-stocked emergency kit, and know how to use your recovery gear in case you get stuck.
Sustainable Overlanding Practices
Leave No Trace Principles
Overlanders have a responsibility to protect the natural environments they explore. Adhering to Leave No Trace principles helps minimize your impact. This includes packing out all trash, avoiding the creation of new trails, and respecting wildlife habitats.
Supporting Local Communities
When passing through small towns and communities, consider supporting local businesses by purchasing supplies, food, and services. This not only helps the local economy but also fosters goodwill between overlanders and the communities they visit.
Conclusion
Overlanding in and around Chicago offers a unique way to experience the Midwest’s natural beauty and hidden gems. From the rolling hills of the Driftless Area to the rugged landscapes of Michigan’s Upper Peninsula, there are countless adventures to be had. By preparing adequately, practicing sustainable travel, and connecting with the overlanding community, you can embark on memorable journeys that showcase the best of what this region has to offer. So, gear up, hit the road, and let the spirit of overlanding guide you through the wonders of Chicago and beyond.