Want to know why Chicago is such a great place to start a Midwest adventure
The Windy City is located in the heartland of America and is the starting point of Route 66.
Road trips from Chicago give you access to a diverse array of destinations. Venture beyond the city’s iconic skyline and buzzing urban lifestyle and you’ll find a multitude of road trip possibilities.
From the scenic shores of Lake Michigan to historic towns, vibrant cities and stunning outdoor landscapes, Chicago is the perfect place to begin your exploration of the Midwest’s diverse attractions.
The Midwest is off-the-beaten-track America at its best and it’s all waiting for you to explore. With easy-to-access car rental for every budget from central Chicago, it’s never been easier to begin your journey
Here’s a quick rundown of ten of the best road trip destinations from Chicag
Milwaukee, Wisconsin
Milwaukee is emerging as a cool destination in its own right and is a regional rival to its bigger Windy City counterpart. Compact and walkable, Milwaukee combines a beautiful lakeside waterfront with historic sites and brewing heritage.
Just 92 miles north along the stunning Lake Michigan shoreline, it’s often the first stop-off point on road trips from Chicago.
Home to iconic breweries like Miller Brewing Company, you can learn about the city’s rich brewing history, visit the Harley Davidson Museum, or hang out in the art galleries, cafes and boutiques of the Historic Third Ward. When you’re tired of the crowds head for the walking and biking trails through Lakeshore State Park.
- Distance from Chicago: 92 Miles
- Driving Time: 1.5-2 Hours
Starved Rock State Park, Illinois
If you’re looking for a refreshing escape from the urban environment then head 90 or so miles southwest of Chicago to Starved Rock State Park.
Renowned for its stunning landscapes, waterfalls, breathtaking sandstone canyons and rich Native American history, it’s a place to pause and breathe in clean a
The park offers over 13 miles of well-maintained hiking trails, providing opportunities for visitors of different fitness levels. As well as walking, Starved Rock State Park offers opportunities for birdwatching, fishing, and picnicking. During the winter months, the park is a popular destination for cross-country skiing and icefall climbing.
- Distance from Chicago: 94 Miles
- Driving Time: 1.5 to 2 Hours
Galena, Ilinois
If you’re looking for old-fashioned American charm then look no further than Galena. Located 164 miles northwest of Chicago nestled along the banks of the Galena River, Galena is the quintessential 19th-century American small town. It’s a must-visit destination for anyone with a love of US history.
With its historic architecture, Victorian homes and well-preserved storefronts, a visit to Galena transports you to a bygone era. In Galena, you’ll also find the former residences of the 18th President of the United States and Civil War hero, Ulysses.S. Grant. Touring the house provides an insight into Grant’s life and his ties to Galena.
The Galena River Trail allows you to explore some of the peaceful natural beauty that surrounds the town.
- Distance from Chicago: 164 Miles
- Driving Time: 3-3.5 Hours
Door County, Wisconsin
With five expansive state parks, charming towns, beaches and wilderness to discover, Door County, Wisconsin is a must-visit destination on road trips from Chicago. Renowned for its maritime charm, rich history, natural beauty and cultural experiences, Door County is an emerging destination that you won’t want to miss.
With its rocky shorelines, lighthouses, sandy beaches, and cherry orchards, Door County provides a perfect blend of natural beauty and cultural experiences. Peppered with charming, picturesque villages such as Fish Creek, Ephraim, and Sister Bay, Door County has a unique character you won’t want to miss.
If you’re looking for a serene retreat from urban life with lots to do and explore, then Door County is a great destination
- Distance from Chicago: 220 to 250 Miles
- Driving Time: 4 to 5 Hours.
St Louis, Missouri
St Louis has always been a melting pot of cultural influences, architecture, food and people making it an exciting destination on road trips from Chicago. Famous for the blues and barbeque, this vibrant city captures the essence of Midwest hospitality and architectural grandeur
Known for its iconic Gateway Arch that graces the city skyline St. Louis boasts a diverse array of attractions and experiences. There are world-class museums and iconic historical attractions like the Saint Louis Art Museum and the Old Court House to explore. If you crave open space after exploring the city then head to the Forest Park, a vast urban parkland bigger than New York’s Central Park. A drive along the scenic Riverfront Trail offers panoramic views of the Mississippi River and the city skyline.
- Distance from Chicago: Around 300 Miles
- Driving Time: 5 Hours
Traverse City, Michigan
Traverse City is a charming resort town situated in Michigan’s northern tip and is surrounded by picturesque vineyards, orchards and the Sleeping Bear Dunes National Lakeshore.
Known as the cherry capital of the world, the region produces a significant percentage of the country’s tart cherries, and visitors can enjoy cherry-themed products and events, as well as an annual cherry festival.
Traverse is also in the Michigan wine-growing region. The Old Mission Peninsula and Leelanau Peninsula are home to numerous wineries where visitors can sample local wines. Vibrant downtown Traverse is home to shops, galleries and restaurants. Clinch Park and Bryant Park are popular spots for sunbathing, swimming, and enjoying the scenic views of Grand Traverse Bay. In winter, Traverse City becomes a hub for winter sports enthusiasts.
- Distance from Chicago: 300 – 350 Miles (Depending on the route)
- Driving Time: Around 5hrs
Amish Country, Indiana
Looking for something completely different?
Then step back in time with a visit to Amish Country. Nestled within the picturesque rolling landscapes of northern Indiana, particularly in regions like Elkhart and LaGrange Counties, Amish communities preserve a traditional way of life long since disappeared from the rest of the USA.
Located in northeastern Indiana, Shipshewana is renowned for its Amish heritage and is home to one of the largest Amish communities in the United States. Visitors can explore the Amish-operated businesses, including furniture shops, quilt stores, and farmers’ markets. In Nappanee, you can tour an authentic Amish farmstead at the Amish Acres Historic Farm & Heritage Resort. Some Amish communities also host seasonal festivals and events that celebrate their heritage, featuring traditional music, food and crafts.
Amish Country is a fascinating place to explore and feels a world away from the bustle of Chicago.
- Distance from Chicago: 100 to 150 Miles
- Driving Time: 2 to 3 Hours
Bloomington, Indiana
Bloomington is frequently named as one of the ‘Coolest Small Cities in America’. This charming college town is not only a relaxed, bohemian destination in its own right but is also surrounded by stunning natural landscapes. Compact and walkable, Bloomington enjoys a vibrant cultural scene, eclectic shops, and a rich array of food and drink. Home to Indiana University, the town buzzes with youthful energy.
If you want to hit the trails you’ll find the Morgan Monroe and Yellowood State Forests nearby, or why not check out the limestone bluffs at the Cedar Bluffs Nature Preserve? The Hoosier National Forest spans over 200,000 acres and provides opportunities for hiking, camping and birdwatching.
- Distance from Chicago: 200 Miles
- Driving Time: 3 to 4 Hours
Saugatuck, Michigan
Saugatuck, Michigan, is a charming and picturesque resort town located along the shores of Lake Michigan. Known for its artistic community, beautiful beaches, and unique attractions, Saugatuck is a popular stop-off point on road trips from Chicago
With its laid-back lakeside location, it’s a great place to spend time on water. The pristine sand dunes and crystal-clear waters of Oval Beach make it a popular spot for sunbathing and swimming. The relaxed vibe continues downtown, with charming shops, boutiques and restaurants to explore on Butler Street. If you’re feeling energetic, climb the stairs in Mount Baldhead Park to enjoy a panoramic view of the town, the Kalamazoo River and Lake Michigan.
- Distance from Chicago:120 Miles
- Driving Time: 2 to 2.5 Hours
Route 66
Route 66 is the most iconic road in North America and the starting point for countless road trips from Chicago. Established in 1926, it travels across eight states, providing a nostalgic journey through diverse landscapes, small towns, and iconic landmarks. The route passes through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.
Completing the entire route is a once-in-a-lifetime experience, and most road-trippers tend to take in a shorter section. Leaving Grant Park in Chicago, a Midwest drive along The Mother Road takes you on a nostalgic journey through the heartland of America, revealing a captivating blend of small-town charm, iconic landmarks, and diverse landscapes. From the historic architecture of Joliet to the cultural treasures of Pontiac, the Midwest miles are the perfect introduction to America’s highway.
- Distance from Chicago: Grant Park in Chicago to Santa Monica Pier in California is approximately 2,448 miles.
- Driving Time: It typically takes around 2 weeks for the entire journey
Ready For Your Next Adventure?
Chicago is the perfect launchpad for your Midwest road adventure. Situated in the heartland of America and boasting the beginning of the iconic Route 66, this vibrant city offers road trippers access to a diverse array of destinations.
Cheaper Than Cars makes it easy to find the perfect vehicle for your big Midwestern adventure whatever your budget. With convenient pickup points in central Chicago, you can be hitting the road in no time at all.
