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We all know that Chicago appears on every “best Midwest” list, but we had to push our eyes back into place when we saw what followed the “Windy City” at Midwest Living’s 2026 awards.
The truth is, the Midwest is more diverse than you might think—very different from abandoned corn fields Ozark madness.
Obviously, small towns are where you’ll find picture-postcard streets and homey charm, but big cities also have a way of defying stereotypes.
The Midwest may not have the Pacific Ocean or the Atlantic Ocean, but numerous lakes are truly breathtaking, even on the shores of urban areas like Chicago and Milwaukee.
But even then there is more to experience than working on your tan in the middle of the country.
That’s why we’ve picked the 4 most surprising ones from Midwest Living award winners which shows that this region has much more to offer than people think.
These 4 surprising cities were crowned the Best in the Midwest for 2026 (in alphabetical order):
Cincinnati
Cincinnati may not be on your bingo card, but we say it’s time to get a new bingo card…
No one plays just one hand.
“Cincy,” as it is known, is practically a two-state destination, located on the Ohio River shared with Kentucky.
While this city may not be exactly known for its tourism, while Columbus is Ohio’s shiny new toy, Cincy radiates with unsuspecting history and revitalized neighborhoods.
In fact, it was once known as the ‘Paris of America’. No, there’s no steel tower to stare at, but if you squint hard enough you can still see the pastime of ‘Parisian’ charm.
Today, it’s a beer-drinking town with the kind of people who live up to the hype that “Midwest is the best.”
As Midwest Living noted, they are host to the largest Oktoberfest in the country!
But if you ask us, it’s best to serve a cold one after a full bowl Horizon Chilea staple of Cincinnati that locals rave about.
Detroit
Has any American city experienced a turnaround as big as Detroit?
We can’t think of any, but Oakland needs to take notes…
Once the wealthiest city in the US, reaching its peak in the 1950s, its years of decline came to a head when it declared bankruptcy in 2013.
After a well-documented rough patch, during which even many locals refused to go out at night due to safety concerns, Detroit has been on the rise in recent years as heavy investment revitalized one of America’s most historically important cities.
Whether you love sports, food, art and culture, or delve deep into history, Detroit has it all, from four Major League sports teams to vibrant neighborhoods like Greek city.
Although Midwest Living is touting Corktown as the new hotspot with a revamped riverfront full of trendy bars and restaurants to check out.
Not to mention, it’s a “border town” with Windsor, Canada, just across the Detroit River, so you can visit two countries in one trip.
Grand Rapids
If we stick with Michigan, there will be no safety or bankruptcy concerns; Grand Rapids is simply underrated.
It’s that simple.
While we can’t guarantee that a Netflix special won’t hit the spine of Amway Grand Plaza, we can guarantee that you’ll have a great time exploring this surprisingly vibrant city packed with art and lush nature.
GR is the best of both worlds for outdoor enthusiasts: you can enjoy the peaceful tranquility of the riverfront and just steps away access day trips to Lake Michigan, where, yes, there are beautiful beaches!
What makes the riverfront even more attractive this year is the festive opening of the Acrisure Amphitheaterwhich is expected to bring A-list entertainment to those who would normally head to Detroit for bigger venues.
Sioux Falls
South Dakota may seem like a snoozer at first glance, but millions of people visit every year to see familiar faces carved into the rocks.
But what else is there to experience?
Besides open meadows of bison and the rumble of Sturgis, you might be surprised to know that Sioux Falls, named for the unmissable waterfalls that run through the heart of the city, is one of the fastest growing destinations in terms of growth and tourism.
You would be shocked by how much shine this city has had if you passed through it years ago.
For example, The Steel District may not have existed. Now it is a bustling hotspot with everything from new must-eats to well-known hotels.
Most notable, however, is that Sioux Falls is very affordable. Their most beautiful hotel in the city center, Hotel on Phillipscan be booked during the spring in the mid-$100s per night.
