The Midwest is one of the most underappreciated regions in the United States. With cities like Chicago and picturesque scenery along the rugged shores of Lake Superior, there are an endless number of places to explore. Whether you’re looking for an urban adventure or to slow down and reconnect with nature, the Midwest holds varied landscapes, like lush forests, serene lakeshores, waterfalls, caves, and caverns, plus so much more. Apple festivals, berry festivals, and arts festivals fill the year with things to do, and friendly communities welcome people into their towns. We will always be ready for a coastal escape, but you can also find us making our way through the slower-paced, diverse goldmine that is the Midwest.

Who doesn’t love a good road trip? One of the best things about Chicago is its central location, which makes it easily accessible to many great destinations across the Midwest. With several states within a reasonable driving distance, there is an endless number of places to choose from for your next weekend retreat or extended getaway. From charming lakeside towns less than two hours away to natural marvels in every direction, while we love our hometown of Chicago, we love to get away from it once in a while, too. Whether you’re a local or visiting, consider one of these memorable road trips for your next adventure. 

In the northwest corner of Michigan’s mitten, a small town called Charlevoix sits on an isthmus between two lakes, connected by a historic drawbridge. With fewer than 2,500 residents, Charlevoix is a tranquil and idyllic town with a genuine Midwestern spirit. Known as the home of the famous Mushroom Houses and surrounded by lakes, neighboring Petoskey often overshadows this charming Michigan town, but it is worth a visit on its own. From cozy coffee shops to ferry rides, Charlevoix might be slower paced, but there’s plenty to keep you busy during a long weekend getaway. We’d even go so far as to say it’s the perfect small town for an extended stay, encouraging slowing down and reconnecting with nature. 

Solo travel is one of the most rewarding experiences. It is liberating to travel without considering anyone else’s opinions or preferences. More importantly, embracing the discomfort of doing everything yourself teaches us much about who we are and our capabilities. Traveling alone means we are forced to have conversations with strangers and figure out the way back to the hotel on our own. Traveling alone is eating in a cafe without company and learning to be comfortable spending time with ourselves. It’s moments of quiet and solitude, and plenty of space to dive into our thoughts. It’s learning who we are without the familiarity of people we know around us. 

One of the things to look forward to the most with a new year is all the new trips there are to plan. Twelve months are a blank canvas to fill with destinations, escapes, cultural immersion, and memories. Whether you prefer to go on grand adventures scaling mountains and reaching high peaks or cozy, slow travel leisurely walking down old, historic cobblestone streets, dipping in and out of bookstores and cafes while getting to know the local people, a new year is a new opportunity to fill as many moments as possible with curiosity and enriching experiences. We'd love to take off for hundreds of places in the world, but these eight are currently at the top of our minds.

Travel was a significant part of my life before the pandemic. Working as a freelancer, I’ve had the privilege of taking my “office” with me, and I took full advantage of that luxury. The pandemic was one of several challenging years, and travel stopped for me months before the world shut down. While I’d like to say that I could fuel that part of me in other ways, it just didn’t seem the same. Coming back to travel in 2024 felt like coming home again.

Happy November! I hope All Hallow’s Eve went without any ghoulish surprises this year and was lots of fun. Now that November is here, fall is in its final few weeks. The leaves are falling rapidly, the colors have changed, and the weather has turned much more brisk. It’s delightful! With four weeks left until Thanksgiving and four weeks between T-Day and Christmas, now is the time to plan a last-minute fall getaway. With limited time to spare, a getaway that’s closer to home makes much more sense. For those of you Chicago-based or Midwest-based, I have five late fall getaways to put on your calendar. It’s a great time to travel to any of these locations because the height of tourist season is over. Rates are dropping and crowds are thinning. Take this as an opportunity to explore each of these Midwestern destinations at your own leisure…