We all know Chicago makes its way on every ‘best Midwest’ listicle, but we had to push our eyeballs back in place when we saw what followed the “Windy City” on Midwest Living’s 2026 awards.
The truth is the Midwest is more diverse than you might think — a far cry from desolate corn fields and Ozark madness.
Obviously, small towns are where you’ll find postcard streets and down-home charm, but major cities have a way of defying stereotypes too.
The Midwest may not have the Pacific or Atlantic, but numerous lakes are truly stunning, even on the shores of urban sprawls like Chicago and Milwaukee.
But even then, there’s more to experience than working on your tan smack dab in the middle of the country.
That’s why we handpicked 4 of Midwest Living’s most surprising award winners that show this region has a lot more going on than people give it credit for.
These 4 surprising cities were crowned best of 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…
Nobody just plays one hand.
“Cincy”, as it’s known, is practically a two-state destination straddling the Ohio River shared with Kentucky.
While this city may not exactly be known for tourism, whereas Columbus is Ohio’s shiny new toy, Cincy is beaming with unsuspecting history and revitalized neighborhoods.
In fact, it was once known as the “Paris of America”. No, there’s no steel tower to gawk at, but if you squint hard enough you can still see its pastime glimmer of ‘Parisian’ charm.
Nowadays, it’s a beer-drankin’ town with the type of people that live up to the hype that “Midwest is best”.
As Midwest Living pointed out, they play host to the largest Oktoberfest in the country!
But, if you ask us, a cold one is best served after a heaping bowl of Skyline Chili, a Cincinnati staple locals rave about.
Detroit
Has any U.S. city seen as big a turnaround as Detroit has?
We can’t think of one, but Oakland should take notes…
Once the richest city in the U.S., hitting its peak in the 1950s, years of decline came to a head with its 2013 bankruptcy.
After a well-documented rough patch, where even many locals refused to go out at night due to safety concerns, Detroit has been on the up-and-up in recent years after hefty investments breathed new life into one of America’s most historically significant cities.
No matter if you’re into sports, food, arts and culture, or deep-diving into history, Detroit has it all from 4 major league sports teams to vibrant neighborhoods like Greektown.
Though 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 double dip 2 countries in one trip.
Grand Rapids
Sticking with Michigan, there’s no safety or bankruptcy concerns to bring up — Grand Rapids is just underrated.
Simple as that.
While we can’t guarantee there won’t be a Netflix special on the backbone of Amway Grand Plaza, we can all but guarantee you’ll have a great time exploring this surprisingly vibrant city brimming with art and lush nature.
G.R. is the best of both worlds for outdoor lovers — you can have the tranquil calm of the riverfront and a stone’s throw access to Lake Michigan day trips, where, yes, there are gorgeous beaches!
Making the riverfront even more alluring this year is the grand opening of the Acrisure Amphitheater, expected to bring A-list entertainment to those who would normally go to Detroit for larger venues.
Sioux Falls
South Dakota may seem like a snoozer at first glance, but millions of people visit each year to see some familiar faces carved into rock.
But what else is there to experience?
Besides open pastures of bison and the rumble of Sturgis, you might be surprised to know Sioux Falls, named after the unmissable falls running through the heart of the city, is one of the fastest-growing destinations in terms of growth and tourism.
You’d be shocked by how much of a glow-up this city has had if you’ve passed through years prior.
For example, The Steel District may not have existed. Now it’s a bustling hotspot with everything from new must-eats to name-brand hotels.
Most notably, though, Sioux Falls is very affordable. Their nicest downtown hotel, Hotel On Phillips, can be booked in the mid $100s per night throughout spring.
