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The Midwest is one of the most oft overlooked regions of the United States. True, it doesn’t have as many National Parks as the West, sun as the South, or history as the Northeast, but the Midwest offers a cultural confluence of east and west, north and south, old and new, and an authentic slice of American culture that’s worth experiencing first-hand. To that end, few cities embody the heartland better than the following five, especially during the glimmering fall season when leaves are changing colors and daytime temps hit the sweet spot.

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Madison, Wisconsin

National Historic Landmark city of Madison, Wisconsin, Midwest USA. Autumn view with bright colored trees along path to the entrance and cloudy sky during later afternoon.

This is the best capital city you’ve probably never visited. Home to the University of Wisconsin-Madison and sandwiched between two beautiful lakes in the heart of America’s Dairyland, Madison served up “farm-to-table” food before we even called it that. For example, The Tornado Room’s tenderloin, The Old Fashioned’s fried cheese curds and burgers, and Babcock ice cream at Memorial Union Terrace on the lakefront are sure to please any foodie. Plus, Madison is loaded with free places to visit including the tall and marble-filled Wisconsin State Capitol, the massive Dane County Farmers Market, the hyper-clean Henry-Vilas Zoo, impressive UW Arboretum, and beautiful Olbrich Botanical Gardens. “Our high taxes have to pay for something!” we heard one local exclaim.

Where to stay: The AC Hotel is a new, hyper modern, and notably welcoming boutique-like hotel just steps away from the iconic State Street and capitol.

St. Louis, Missouri

City of St. Louis skyline. Image of St. Louis downtown at twilight.

It’s hard to believe this used to be the western edge of the American frontier. But it’s easy to see for yourself, especially at the moving and recently renovated Gateway Arch National Park. Whether at the underground museum or taking in the impressive view from the Arch’s top where you can see “the past” while looking riverside and “the future” while looking westward over the city. Catch a baseball game among a sea of red at the fan-favorite Busch Stadium, home of the Cardinals, the second winningest team in Major League history. Channel your inner-child at the award winning City Museum, a labyrinth of Fraggle-rock like tunnels and height-fright inducing outdoor playground for all ages. Like Madison, St. Louis is also notable for its love of dairy foods, namely gooey butter cakes, frozen custard and Provel cheese pizza. You can also get a wonderful three-macro meal at either The Fountain or Pappy’s Smokehouse. Better yet, have a blast traversing this manageable and scenic city with the help of several scooter share apps.

Where to stay Hotel Saint Louis is a historic and delightful downtown stay and just a short walk from virtually everything.

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Minneapolis, Minnesota

Photo courtesy of Blake Snow

Arguably the quietest city on this list, towering and glass-filled Minneapolis is no less beautiful or deserving of a visit. As the only metropolis in the upper Midwest, its name literally means “water city,” thanks to its 22 natural lakes and the gushing blue Mississippi River. Its streets and sidewalks are canopied by trees, and its modern transportation and infrastructure are ranked among the best in the nation. Tour the Chain of Lakes (Cedar, Isles, Bde Maka Ska, Harriet and Nokomis) and ride the trolley between Bde Maka Ska and Harriet lakes, bike the town or pair a stroll around town with great bites via Twin Cities Food Tours. The city is best visited during the bug-free months of autumn.

Where to stay Loews Minneapolis Hotel in downtown is perfectly situated, and offers the same high-standard as the chain’s other namesake lodgings.

Chicago, Illinois

Chicago skyline view from autumn park, city of Chicago downtown skyscrapers cityscape, Illinois, USA

If you visit only one city from this list, make it this one. Why? Chicago is proof that a city of millions doesn’t have to be smelly, rude or trashy. In fact, Chicago is delightfully flower-filled, full of clean sidewalks, and boasts world-class architecture you’ll never tire craning your neck at. Unlike NYC, Chicago doesn’t bear down on you. Its skyscrapers are spaced in a way that let you appreciate all the towering steel and concrete around you. And its outdoor attractions—notably Millennium Park, Buckingham Fountain, Wrigley Field, architectural river cruises, and both urban and Lakefront biking trails, are a breath of fresh air. But “The Chicago Way” doesn’t stop there. Its distinctive food is equally worth writing home about, namely Lou Malnati’s phenomenal deep dish sausage pizza, Portillo’s dipped Italian beef sandwiches and chopped salads, Bub City’s delectable Trucker Snacks, or any Chicago-style hot dog that’s “dragged through the garden.”

Where to stay The Gwen on Michigan Avenue features one of the best American tapas restaurants in the city, plus amazing views of downtown.

Rapid City, South Dakota

Bad Lands

Badlands National Park

I know what you’re thinking: “Is South Dakota in the Midwest?” The answer is yes, if only by technical default, since Rapid City is neither West, South or Northeast. Regardless, this beautiful small city is the best portal to the unsung Black Hills, one of the region’s most mesmerizing landscapes. Highlights include Badlands National Park, Mount Rushmore, Custer State Park, Devil’s Tower (in Wyoming) and Buffalo Gap National Grasslands. Even Dinosaur Park is kitschy and fun. Either way, you’re sure to enjoy this Midwest outpost and will probably be amazed by all of the surrounding great outdoors. 

Where to stay: Cambria Hotel in downtown Rapid City is a modern, comfortable, and highly affordable portal to the best of the city.

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Tagged: Chicago, Chicago, Midwest, Minnesota

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Blake Snow

Blake Snow

Blake writes for fancy publications and Fortune 500 companies as a seasoned writer-for-hire and energetic travel columnist. He lives in Provo, Utah with his loving family and loyal dog, and hopes to visit all seven continents someday.

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