Best Road Trips from Chicago: Exploring the Great Lakes Region

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If you’re looking for an adventure that’s not too far from Chicago, a road trip might be just what you need. The Midwest is full of hidden gems waiting to be discovered, and there are plenty of road trips from Chicago that will take you to some of the best spots. Whether you’re looking for a quick weekend getaway or a longer trip, there’s something for everyone.

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One of the best road trips from Chicago is the Great River Road in Illinois. This scenic drive takes you along the Mississippi River and through charming towns like Galena and East Dubuque. You’ll see historic sites, beautiful scenery, and plenty of opportunities for outdoor activities like hiking and fishing. The drive takes about 3.5 hours, making it a great option for a weekend trip.


Another great road trip is to Harbor Country, Michigan. This idyllic shoreline in Michigan’s southwestern corner stretches from the Indiana border to the town of Sawyer and is only 1 hour and 20 minutes from Chicago. Harbor Country is one of the most popular getaway destinations for Chicagoans.

You’ll find picturesque beaches, quaint towns, and plenty of opportunities for outdoor activities like hiking and biking. Whether you’re looking for a relaxing beach vacation or an active adventure, Harbor Country has something for everyone.

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Understanding Road Trips

Going on a road trip can be an exciting and memorable adventure, but it requires some planning to ensure a successful trip. In this section, we’ll discuss the importance of planning and choosing the right vehicle for your road trip.

Importance of Planning

Planning is crucial for a successful road trip. By planning ahead, you can ensure that you have everything you need for the trip and avoid any unexpected surprises. Here are some things to consider when planning your road trip.

  • Route: Decide on your route and plan your stops and attractions along the way. Use online maps or road trip planning websites to help you plan your route.
  • Accommodations: Book your accommodations in advance to ensure you have a place to stay each night. Consider staying in hotels, motels, or even camping if you prefer.
  • Budget: Plan your budget for the trip, including food, gas, and any activities or attractions you plan to visit.
  • Packing: Pack everything you need for the trip, including clothes, toiletries, snacks, and any necessary equipment or supplies.

By planning ahead, you can ensure that your road trip is enjoyable and stress-free.

Choosing the Right Vehicle

Choosing the right vehicle for your road trip is also important. You want a vehicle that is comfortable, reliable, and can handle the terrain and weather conditions of your route. Here are some things to consider when choosing a vehicle.

Best Road Trips from Chicago consider the size of vehicle
  • Size: Consider the size of your group and the amount of luggage or equipment you’ll be bringing. Make sure the vehicle has enough space to accommodate everything comfortably.
  • Fuel Efficiency: Choose a vehicle that is fuel-efficient to save money on gas during your trip.
  • Comfort: Look for a vehicle that is comfortable to ride in for long periods of time. Consider features like air conditioning, comfortable seats, and plenty of legroom.
  • Reliability: Choose a vehicle that is reliable and has a good track record for safety and performance.

By choosing the right vehicle, you can ensure that your road trip is comfortable, safe, and enjoyable.

Remember, planning ahead and choosing the right vehicle are key to a successful road trip. With a little preparation, you can have a memorable adventure on the open road.

Chicago: The Starting Point

If you’re looking for a great starting point for a road trip, look no further than Chicago. This bustling city is located in the heart of the Midwest, making it the perfect jumping-off point for exploring the region. Whether you’re looking for natural beauty, historic sites, or big-city excitement, there’s something for everyone within a few hours’ drive of Chicago.

One of the best things about starting your road trip in Chicago is the sheer number of options available to you. From the city itself to the surrounding suburbs and countryside, there’s no shortage of things to see and do. Plus, with major highways like I-90 and I-94 passing through the city, it’s easy to hit the road and start your adventure.

If you’re interested in exploring the city before you hit the open road, there’s plenty to keep you busy. Take a stroll through Millennium Park and snap a selfie in front of the famous Bean sculpture. Visit the Art Institute of Chicago to see some of the world’s greatest works of art. Or take a stroll down the Magnificent Mile for some world-class shopping.

Once you’re ready to hit the road, you’ll find plenty of options for road trips from Chicago. Head north to explore the shores of Lake Michigan, or head south to experience the rolling hills of southern Illinois. Or, if you’re feeling ambitious, head west to explore the Great Plains and the Rocky Mountains.

No matter which direction you choose, you’re sure to find plenty of adventure and excitement on your road trip from Chicago. So pack your bags, hit the road, and get ready for an unforgettable journey through the heart of America.

Midwest Gems: Stops to Make

If you’re planning a road trip from Chicago, the Midwest offers plenty of hidden gems to explore. Here are a few must-see stops to add to your itinerary.

Milwaukee, Wisconsin

Just a two-hour drive north of Chicago, Milwaukee has something for everyone. Known for its breweries and cheese curds, the city also boasts beautiful lakefront views, historic architecture, and a thriving arts scene. Be sure to check out the Milwaukee Art Museum, the Harley-Davidson Museum, and the Pabst Mansion.

Minneapolis, Minnesota

A six-hour drive northwest of Chicago, Minneapolis is worth the trip. The city is home to numerous parks and lakes, including the famous Chain of Lakes. Minneapolis is also known for its food scene, with plenty of trendy restaurants and food halls to check out. Don’t miss the iconic sculpture garden at the Walker Art Center.

Fargo, North Dakota

Best Road Trips from Chicago largest buffalo statue

If you’re up for a longer drive, Fargo is a unique destination to consider. The city is known for its friendly locals, quirky attractions, and rich history. Check out the Fargo Air Museum, the Plains Art Museum, and the iconic woodchipper from the movie Fargo. And of course, don’t forget to take a photo with the famous “largest buffalo statue” in nearby Jamestown.

No matter which Midwest gems you choose to visit, you’re sure to find plenty of charm, culture, and adventure along the way.

Scenic Routes to Consider

If you’re looking for a scenic road trip from Chicago, you have plenty of options to choose from.

Great River Road

The Great River Road is a scenic byway that follows the Mississippi River from its headwaters in Minnesota to the Gulf of Mexico. The Illinois portion of the Great River Road runs for 550 miles along the western border of the state. The road takes you through charming river towns, past historic sites, and offers stunning views of the Mississippi River.

Some highlights of the Great River Road in Illinois include:

  • Galena: This charming town is known for its historic architecture, quaint shops, and scenic views of the river.
  • Mississippi Palisades State Park: This park offers hiking trails, camping, and stunning views of the river from its bluffs.
  • Nauvoo: This historic town was once the headquarters of the Church of Jesus Christ of Latter-day Saints. Today, it’s a popular tourist destination with historic sites and beautiful views of the river.

Lake Michigan Circle Tour

The Lake Michigan Circle Tour is a 1,100-mile scenic route that takes you around Lake Michigan. The route passes through four states: Illinois, Indiana, Michigan, and Wisconsin. The Illinois portion of the tour takes you along the eastern shore of Lake Michigan, from Chicago to the Wisconsin border.

  • Chicago: The tour starts and ends in Chicago, a world-class city with plenty of attractions to explore.
  • Indiana Dunes National Park: This park offers 15 miles of sandy beaches, dunes, and hiking trails along the southern shore of Lake Michigan.
  • Illinois Beach State Park: This park offers swimming, hiking, and camping along the shores of Lake Michigan.
  • North Point Lighthouse: This historic lighthouse in the town of Lake Bluff offers stunning views of the lake and surrounding area.

No matter which route you choose, you’re sure to find plenty of scenic views and interesting attractions along the way.

Preparing for the Journey

Before embarking on your road trip from Chicago, it’s important to prepare for the journey ahead. This includes packing essential items and ensuring that your vehicle is in good condition.

Packing Essentials

Packing for a road trip requires some planning to ensure that you have everything you need without overpacking. Here are some essential items to consider bringing with you:

  • Maps or a GPS device: Even if you have a GPS device, it’s always a good idea to bring a physical map as a backup.
Best Road Trips from Chicago snacks and drinks
  • Snacks and drinks: Pack non-perishable snacks and drinks to keep you fueled up during your journey.
  • First Aid Kit: It’s always better to be safe than sorry. A basic first aid kit can come in handy in case of minor injuries.
  • Comfortable clothing and shoes: Pack comfortable clothing and shoes that are appropriate for the weather and any activities you plan to do.
  • Entertainment: Bring books, music, or games to keep you entertained during long stretches of driving.

Vehicle Maintenance

Before hitting the road, it’s important to ensure that your vehicle is in good condition.

  • Oil change: Get an oil change if it’s due or overdue.
  • Tire pressure: Check your tire pressure and inflate them to the recommended level.
  • Fluid levels: Check your vehicle’s fluid levels, including brake fluid, coolant, and transmission fluid.
  • Brakes: Have your brakes checked to ensure that they are in good condition.
  • Battery: Check your battery to ensure that it’s in good condition and fully charged.

By packing essential items and ensuring that your vehicle is in good condition, you can have a safe and enjoyable road trip from Chicago.

Adventures Beyond the Midwest

If you’re looking for a longer road trip adventure, there are plenty of options beyond the Midwest. Here are two popular road trip destinations that are worth the extra mileage.

Rocky Mountain Road Trip

Head west for a Rocky Mountain road trip that will take you through some of the most stunning natural landscapes in the country. Start in Denver, Colorado, and drive through the Rocky Mountains to see towering peaks, crystal-clear lakes, and picturesque valleys. Stop in Boulder for a hike up to the Flatirons or a stroll down Pearl Street, a pedestrian mall with plenty of shops and restaurants.

Best Road Trips from Chicago Rocky Mountain National Park

From there, drive through the Rocky Mountain National Park to see elk, bighorn sheep, and other wildlife in their natural habitats. You can also take a scenic drive along the Trail Ridge Road, which offers breathtaking views of the mountains and valleys below.

Pacific Coast Highway

For a road trip with a coastal view, head west to California and drive along the Pacific Coast Highway. Start in San Francisco and drive down the coast to Los Angeles, stopping at scenic beaches, charming towns, and iconic landmarks along the way.

In San Francisco, take a walk across the Golden Gate Bridge or visit Alcatraz Island. In Big Sur, stop at Pfeiffer Beach to see the famous Keyhole Arch or take a hike through the redwood forests at Julia Pfeiffer Burns State Park. In Los Angeles, visit the Hollywood Walk of Fame or take a stroll down Venice Beach.

No matter which road trip you choose, be sure to pack plenty of snacks, water, and supplies for the journey. And don’t forget to take breaks and enjoy the scenery along the way!

Final Thoughts on the Best Road Trips from Chicago

There are many road trip options to explore from Chicago. Whether you’re looking for a quick weekend getaway or a longer adventure, there is something for everyone.

Some of the most popular road trips from Chicago include heading to St. Louis, Indianapolis, or Milwaukee. These cities offer a mix of urban and outdoor attractions, making them great destinations for families, couples, or solo travelers.

If you’re looking to get out into nature, consider visiting the Indiana Dunes National Park or the Upper Peninsula of Michigan. Both offer stunning natural beauty and a range of outdoor activities, including hiking, biking, and kayaking.

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For those interested in history, the Route 66 road trip is a must-do. This iconic highway stretches from Chicago to Santa Monica, California, and offers a glimpse into America’s past.

No matter which road trip you choose, be sure to plan ahead and pack accordingly. Consider renting a car or RV to make the journey more comfortable, and don’t forget to bring snacks, water, and a camera to capture all the memories. Happy travels!

Frequently Asked Questions about Best Road Trips from Chicago

What are some of the best Midwest road trips to take from Chicago?

Chicago is the perfect starting point for a Midwest road trip.

  • St. Louis, MO: This city is known for its beer, blues, and BBQ. It’s only a 4.5-hour drive from Chicago and definitely worth the trip.
  • Indiana Dunes, IN: Only an hour away from downtown Chicago, Indiana Dunes became the newest National Park in the United States in 2019.
  • Mississippi River Drive to East Dubuque, IL: This drive along the Mississippi River is filled with historical sites and activities. Moline and Rock Island are two cool detours, but East Dubuque is a must-visit for its Chicago Great Western Railway Depot Museum.

What are some day trip options in Southern Illinois from Chicago?

  • Starved Rock State Park: This state park is only a 2-hour drive from Chicago and offers beautiful hiking trails and waterfalls.
  • Shawnee National Forest: This national forest is known for its beautiful scenery and hiking trails. It’s only a 5-hour drive from Chicago.
  • Galena, IL: This charming town is known for its historic architecture and quaint shops. It’s only a 3-hour drive from Chicago.

What are some warm destinations to drive to from Chicago?

  • Nashville, TN: This city is known for its live music and southern charm. It’s only an 8-hour drive from Chicago.
  • New Orleans, LA: This city is known for its delicious food and lively atmosphere. It’s a 13-hour drive from Chicago, but definitely worth the trip.
  • Gulf Shores, AL: This beach town is perfect for a relaxing getaway. It’s a 12-hour drive from Chicago.

What are some great road trips from Chicago for couples?

  • Door County, WI: This charming town is known for its beautiful scenery and quaint bed and breakfasts. It’s only a 4-hour drive from Chicago.
  • Traverse City, MI: This city is known for its wineries and beaches. It’s a 6-hour drive from Chicago.
  • Lake Geneva, WI: This town is known for its beautiful lake and charming downtown area. It’s only a 2-hour drive from Chicago.
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What are some family-friendly road trip options from Chicago?

  • Wisconsin Dells, WI: This city is known for its water parks and family-friendly activities. It’s only a 3-hour drive from Chicago.
  • Mackinac Island, MI: This island is known for its beautiful scenery and family-friendly activities. It’s a 7-hour drive from Chicago.
  • Springfield, IL: This city is known for its history and family-friendly attractions, such as the Abraham Lincoln Presidential Library and Museum. It’s only a 3-hour drive from Chicago.

What are some short road trips that can be taken from Chicago?

  • Milwaukee, WI: This city is known for its breweries and museums. It’s only a 1.5-hour drive from Chicago.
  • Lake Geneva, WI: This town is known for its beautiful lake and charming downtown area. It’s only a 2-hour drive from Chicago.
  • Starved Rock State Park: This state park is only a 2-hour drive from Chicago and offers beautiful hiking trails and waterfalls.

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