Road Trip! The Best Travel Destinations Within Driving Distance of Chicago

While the Northeast is repeatedly featured for having the best fall foliage, there’s a Midwest destination gaining well-deserved attention for its leaf peeping, and it’s in Northern Michigan. Though usually seen as a summer vacation spot, Glen Arbor is a four-season destination with unique activities all year round – especially in the fall months. The harvest season in Michigan is unparalleled to any other state thanks to the influence that the Great Lakes play in both the fertilization and aesthetics of the area. The Glen Arbor region is home to quaint communities, extensive state and national forests and picturesque vistas of Lake Michigan that exemplify the beauty of the Great Lakes state.

This historic city on the Ohio River offers top cultural institutions and a revitalized riverfront. For many years dubbed underrated to those that dwell in the city, people are just starting to realize just how special Cincinnati is. What is now dubbed the mecca of entrepreneurship in the Midwest, what also makes it ideal are the new restaurants and experiences that have opened almost weekly over the past few years. Combine that with a rich history and a strong sense of Cincy pride, and you’ve got the making of The Queen City. It’s a river town, a sports town, a metropolis with architectural landmarks, and—since the opening of the $110 million National Underground Railroad Freedom Center in 2004—a history town.

Minneapolis is an under-the-radar midwestern gem that’s known for its music and theater scene, great restaurants, breweries, and art galleries galore. Though we won’t be able to participate in some of these public activities for a little while, the city’s iconic history will still draw you in with its range of socially distant activities. Minneapolis evokes the roaring 1920’s with a hustle and bustle that’s balanced out by national parks, lakes and 200 miles of bike trails that beckon travelers on warm, sunny afternoons. Truly immerse yourself in this cultural oasis, and build your itinerary based on your personal preferences as music festivals, art shows, conventions, and games are available all year round.

The much buzzed about revitalization of Detroit makes it a natural hot spot to want to see for yourself. With the booming culinary scene, growing arts community and refurbishment of historic buildings into hot spots, it’s also a mecca for Black entrepreneurship and culture — so you’ll feel at home on your first visit. Detroit’s up-and-coming culinary scene is no secret due to hot, young chefs that are getting creative in the kitchen with an emphasis on locally sourced, seasonal menus and a booming craft beer scene, while a new class of artists are also helping to revitalize the Motor City.

While you may be familiar with Madison because of its cheese roots, this state capital is a destination to be treasured (even during the cold winter months), with its beautiful sights and prime location surrounded by two large lakes. Known for its shopping, cultural events and architecture, the food scene is virtually unrivaled for a city of its size. And if you’re looking for socially distant activities to soak in the views and the vibes, The Capital City trail winds around Lake Monona (the smaller of the two lakes) and provides plenty of picturesque stops for an Instagram of the skyline.

Just across the Mississippi River from Illinois lies the scenic city St. Louis. Its rich musical history, primarily focused on the blues, compliments its culinary scene, combining modern cuisine with traditional favorites like toasted ravioli and gooey butter cake. The beer history in St. Louis is tied to Anheuser-Busch, and the more recent popularity of its craft beer scene makes it a great spot to taste many different flavors. Forest Park and the newly renovated Gateway Arch Park provide beautiful green spaces for visitors to enjoy.

Located just 100 miles southwest of Chicago, you’ll find a socially distant nature area that will not only bring peace of mind, but also peace of heart. Offering an ideal spot to enjoy nature with more than a dozen sandstone canyons along with beautiful waterfalls, Starved Rock State Park is the hidden gem you didn’t know you need. No matter the season, hiking is ideal, so as you walk through the tranquil forest, keep an eye out for deer and birds, including bald eagles, along the way. If you visit during the fall, it’s filled with vibrant foliage, and in winter you can even go ice climbing.