6 Best Road Trips From Chicago

1. The Great River Road (Illinois & Wisconsin)

Embark on a scenic journey along the mighty Mississippi River. The Great River Road offers breathtaking views, historic river towns, and a glimpse into the heartland of America. Starting just south of Chicago, this route follows the river north through Illinois and into Wisconsin, allowing you to experience the beauty of the Midwest at your own pace.

Highlights:

• Galena, IL: A charming historic town with well-preserved 19th-century architecture.
• Starved Rock State Park: Stunning canyons, waterfalls, and hiking trails.
• Wisconsin Dells: The "Waterpark Capital of the World" for family fun.
• Dubuque, IA (slightly off the main route, but worth the detour): Explore the National Mississippi River Museum & Aquarium.

2. Indiana Dunes National Park Loop

Escape the city bustle and discover the surprisingly beautiful Indiana Dunes National Park. This road trip offers a mix of sandy beaches, towering dunes, and lush forests, all just a short drive from Chicago. It's a great option for a weekend getaway filled with outdoor adventures.

Highlights:

• Indiana Dunes State Park: Explore the iconic dunes and enjoy swimming and sunbathing on Lake Michigan.
• Mount Baldy: Climb the tallest dune in the park for panoramic views.
• Porter Beach: A popular beach with stunning sunsets.
• Hiking Trails: Numerous trails winding through the park's diverse ecosystems.

3. Door County, Wisconsin: The "Cape Cod of the Midwest"

Head north to Door County, Wisconsin, a peninsula renowned for its picturesque coastline, cherry orchards, and charming villages. This road trip is perfect for those seeking a relaxing escape with stunning scenery and delicious local food.

Highlights:

• Peninsula State Park: Offers hiking, biking, camping, and scenic overlooks.
• Fish Creek: A quaint village with shops, galleries, and restaurants.
• Ephraim: A historic village known for its iconic white church and stunning harbor views.
• Cherry Picking: Visit a cherry orchard and pick your own fresh cherries during the season.
• Lighthouses: Explore the many historic lighthouses that dot the coastline.

4. Route 66: A Slice of Americana

Experience a nostalgic journey along a section of the iconic Route 66. While you can't drive the entire historic route from Chicago, a portion of it runs through Illinois, offering a taste of classic Americana. Visit quirky roadside attractions, retro diners, and small towns that evoke the spirit of a bygone era.

Highlights:

• Pontiac, IL: Home to numerous Route 66 murals and the Route 66 Hall of Fame and Museum.
• Atlanta, IL: See the "Tallest Man on Route 66," a giant fiberglass statue.
• Chenoa, IL: A charming town with a historic downtown district.
• Funks Grove Pure Maple Sirup: A family-owned maple syrup farm with tours and tastings.

5. Michigan's West Coast: Beaches, Breweries, and Beauty

Discover the beauty of Michigan's west coast with a road trip along Lake Michigan. This route offers stunning beaches, charming beach towns, and a thriving craft beer scene. It's a great option for a weekend getaway filled with sun, sand, and delicious brews.

Highlights:

• South Haven: A popular beach town with a vibrant downtown area.
• Saugatuck: A charming art town with galleries, shops, and restaurants.
• Holland: Known for its Dutch heritage and tulip festivals.
• Grand Haven: Home to a beautiful boardwalk and a musical fountain.
• Microbreweries: Numerous award-winning microbreweries along the coast.

6. Indianapolis, Indiana: Urban Exploration

For a shorter road trip, head to Indianapolis, Indiana, a vibrant city with a rich history and a thriving arts and culture scene. Explore the city's museums, monuments, and parks, and enjoy its diverse culinary offerings.

Highlights:

• Indianapolis Motor Speedway Museum: Learn about the history of the Indy 500.
• White River State Park: A beautiful urban park with museums, gardens, and trails.
• Indianapolis Museum of Art at Newfields: Explore a diverse collection of art.
• Monument Circle: A historic landmark with a towering monument honoring Civil War veterans.
• Canal Walk: A scenic pathway along the canal, perfect for walking or biking.

Here's a quick overview to help you decide which road trip is right for you:

No matter which road trip you choose, you're sure to have an amazing adventure exploring the region around Chicago. So pack your bags, grab your keys, and get ready to hit the open road!