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Chicago Scenic Drives

Top 10 Chicago road trips

  1. Indianapolis, IN
  2. Lake Geneva, WI
  3. Starved Rock State Park, IL
  4. Door County, WI
  5. Shawnee Hills Wine Trail, IL
  6. Galena, IL
  7. Cahokia Mounds, IL
  8. Nashville, TN
  9. Greenfield Village, MI
  10. Milwaukee, WI

Chicago is such a popular centre of art and culture that some call it a microcosm of the entire United States. However, as veteran visitors to the Windy City would argue, it isn’t just a great destination in itself – it’s also an excellent base from which you can make road trips to other unique places. The next time you feel saturated with the bustle of Chicago, consider hitting the road for a week or longer.

10 of the best scenic drives from Chicago

Here’s a list of our ten favorite getaway destinations for a road trip from Chicago, all less than a day’s drive from the city. Each will need at least two days to explore. If you’ve got the time, try and fit several of them into the same trip.



Indianapolis

1. Indianapolis, IN

Indianapolis, capital of Indiana, is best known for three things: sports, sandwiches and museums. If you visit in May, be sure to watch the Indianapolis 500, one of the most famous motor racing events in the Americas. When you’re hungry, snack on a pork tenderloin sandwich, the city’s signature dish. To get a sense of the city’s cultural scene, take your pick of the city’s museums, of which there are at least twenty.

Begin with the Children’s Museum of Indianapolis, the largest children’s museum in the world and home to the famous T-Rex skeleton nicknamed Sue. Its prehistoric exhibits include not only dinosaur fossils, but also fossils of sea reptiles, pterosaurs and ancient mammals. Children also love the museum’s carousel, theatre for live performances, and pop culture gallery.

Adults might be more interested in the Indiana State Museum, which traces the history of Indiana State, or the Eiteljorg Museum of American Indians and Western Art, with its massive collection of contemporary Native American pieces.

Lake Geneva, WI

2. Lake Geneva, WI

Lake Geneva isn’t a lake – it’s a town on a lake, and the lake in question is Geneva Lake. Confusing? Don’t worry, it’ll stick in your head after a day or two spent here. There are plenty of opportunities for boating, cruising and even yacht racing in this part of Wisconsin.

On the 26-mile-long Geneva Lake Shore Path, retrace the steps of the Native tribes who, for thousands of years, skirted the perimeter of the lake. Most of the path is now owned by private homesteaders who fled to Lake Geneva after the Great Chicago Fire of 1871. Some properties are open to the public, so feel free to walk through and admire the unique decor en route, but others are sealed off, and these you should definitely avoid.

The other place in Lake Geneva you should check out is its museum, which displays old farm implements, arrowheads from the Potawatami tribe and a recreation of the old thoroughfare containing buildings like a general store and dental station.

Starved Rock State Park, IL

3. Starved Rock State Park, IL

Legend has it that at a meeting between the Illinois, Ottawa and Potawatami tribes, a hotheaded young Illinois warrior attacked the Ottawa chief, Pontiac, sparking a tribal feud. Fearing retribution, the Illinois delegation fled to a rock in the forest and hid there, hoping to leave once the Ottawa gave up their search, but unfortunately for them, the Ottawa never left the area. As a result, the Illinois starved to death. In time the rock came to be known as Starved Rock.

Faithful to its dark history, the Starved Rock State Park has a sort of imposing beauty. With 18 sandstone canyons, seasonal waterfalls, fishing spots along the Illinois River, and 13 miles of hiking trails, it is one of the state’s best outdoors attractions. Even if you aren’t in the mood to explore it by foot, you can still enjoy it by joining a trolley tour.

Door County, WI

4. Door County, WI

Door County, the ‘Cape Cod of the West,’ is surrounded by water on three sides and has over 300 miles of shoreline. Yes, this means plenty of beaches to explore! If you’re traveling with family, try Nicolet Beach or Egg Harbor Beach. If you’re alone though, you’d probably prefer the solitude of Ridges Beach.

The waters surrounding the peninsula are dotted with several lighthouses, most of them built in the 1800s, that have saved many a lost ship from disaster. Some of these are still in use and can only be visited at fixed times during the year while others serve solely as historic sites.

Once you go inland, you’ll find that Door County is home to a number of unique state parks, art galleries, cherry orchards and wineries. While you’re here, be sure to watch a play in the Northern Sky Theater, easily the most beautiful outdoor performance venue in the region.

Shawnee Hills Wine Trail, IL

5. Shawnee Hills Wine Trail, IL

You’ve probably heard of the legendary wines of the Napa Valley, but what about those of the Shawnee Hills (which are just as good)? Located within the Shawnee National Forest are eleven wineries to make your trip in the woods truly special. You can cover all of them by following the 40-mile Shawnee Hills Wine Trail, the oldest wine trail in Illinois state. If you find yourself unwilling to leave before sundown, you can put up at one of many B&B places.

Besides the fact that it houses a wine trail, the Shawnee National Forest is special for being one of the few forests left in Illinois so when you’ve finished savouring the spirits on offer here, go on a hike. In some parts, you’re even allowed to go rock climbing and rappelling so prepare for a truly wild couple of days.



Galena, IL

6. Galena, IL

Galena, situated in northwestern Illinois, is a historic town with a number of 18th century buildings now serving as museums. The most famous of these converted buildings is the Ulysses S Grant House, once owned by the 18th President of the US. Built in the Italianate style, the house was in fact not constructed by Grant; in reality, it was gifted to him by the locals, who wanted to thank him for his role commanding troops in the Civil War.

But not all of Galena’s old houses have positive vibes. If you take a ghost tour, you’ll have the chance to explore old parts of the city – parts that may or may not really be haunted but sure do have interesting stories attached to them.

Main Street has the best restaurants in town. Be sure to taste some of the fudge on sale here. Afterwards, check out some of the antique shops for souvenirs to take home.

Cahokia Mounds, IL

7. Cahokia Mounds, IL

The Cahokia Mounds State Historic Site is the largest pre-Columbian city complex north of Mexico. Archaeologists estimate that at its peak, this UNESCO World Heritage Site was even more populous than London. No one is entirely sure what the mounds were used for, though popular theories state that they belonged to the nobles and fulfilled some ceremonial purpose.

Most of Cahokia’s remains have been lost to the sands of time, making it hard for visitors to imagine what the city looked like eight hundred years ago. The historic site’s support group aims to remedy this with the help of an augmented reality (AR) tour. Once completed, this will superimpose images of pre-Columbian Cahokia over the existing landscape, letting people literally see the grandeur of America’s ancient civilizations. However, even without this technology, it isn’t hard to imagine the genius of a people that developed complex urban societies thousands of years before the first Europeans arrived.

Nashville, TN

8. Nashville, TN

Nashville, capital of Tennessee, greatly prides itself on its culture, going so far as to call itself the Athens of the South. It even has its own version of the Parthenon, built to scale and containing a massive statue of the Greek god Parthenos.

There are two museums you should visit in Nashville, both revolving around the music of the US. The first of these is the Country Music Hall of Fame and Museum, which records the history of America’s vernacular music via moving images, photographs, instruments, song manuscripts and other paraphernalia. The second is the Grammy Museum Gallery, which focuses on the development and distribution of the popular Grammy awards. If these museums make you want to listen to some live music, book tickets to a show at the Grand Ole Opry, one of America’s most epic performance venues.

Greenfield Village, MI

9. Greenfield Village, MI

Also called The Henry Ford Village, Greenfield Village in Michigan is a massive outdoor museum that celebrates some of America’s greatest innovations in science and technology. Some of its exhibits include the laboratory where Thomas Edison developed the first lightbulb, the workshop once owned by the Wright brothers, and a whole series of Model T’s, the first cars that were affordable to middle class Americans.

The museum, which spans 80 acres, is also home to some historic artifacts associated with the progressive movements of the mid 1900s. One of these is the Montgomery bus in which Rosa Parks, an African-American seamstress, sat in defiance of segregation laws at the time, marking the beginning of the Civil Rights Movement.

Milwaukee, WI

10. Milwaukee, WI

It isn’t for nothing that Milwaukee is called the Brew City. Four of the country’s most successful beer barons – Miller, Schlitz, Pabst and Blatz – had their roots here. Today, visitors here are encouraged to learn more about the early days of brewing by going on tours that take them to over 30 popular breweries. That’s a lot of alcohol to taste, so make sure you do it over a couple of days.

If you’re a motorbike nerd, visit the Harley-Davidson Museum. Here you’ll find over 450 motorbike models, including the very first – Serial Number One. The museum also houses thousands of artifacts from the Harley-Davidson Motor Company.