There’s no Midwest city more famous than Chicago. Next up, it’s up to your discretion. St. Louis, Cleveland, and even ever-so-trendy Indianapolis are all in the mix.
If we’re being honest, not every Midwest city, no matter how well-known or hyped, is worth visiting.
I mean, when’s the last time you heard about someone vacationing in Des Moines?
Fat chance.

That said, financial wizards at GoBankingRates crunched some numbers for us, so we can reveal the best places to visit the Midwest without breaking the bank or being bored to tears.
Our expert team here at Travel Off Path hand-picked 4 of the most worthwhile destinations from their insightful list that will surely wow you, from timeless small towns to cities once known for their Paris vibes.
4) Saint Paul, MN: Swap The Coast For Crowd-Free Lakes
Many say Minneapolis is one of America’s most underrated cities. Taking another step further, sister city Saint Paul (or brother city?), is even more underrated and easily accessible if you fly into Minneapolis.

We all know Minnesota as the ‘land of 10,000 lakes’. Many of the most worthy of a visit are in St. Paul’s vicinity.
Dozens of lakes surround the city’s vibrant downtown, gleaming with surprising eye-popping architecture from the state capitol to the rows of Victorian marvels along Summit Avenue.
Como Lake is one of the closest and arguably the most enjoyable. Plus, the Como Park Zoo & Conservatory is next door, so you can make a whole day out of one spot.
Best of all, Saint Paul will soon be easier to reach than ever with Allegiant taking over Minneapolis-based Sun Country Airlines, so you should have no problem scoring cheap airfare.

According to GoBankingRates, expect to budget for the following:
- Airfare for couple: $912 (likely not factoring Allegiant – Sun Country merger)
- Total hotel costs: $323
- Total meals: $417
- Total drinks: $52
- Total for entire vacation: $1,705
3) Kansas City: A Rare 2-For-1 Vacation
Largely known as a rootin’ tootin’ sports town as an excuse to gather and indulge in world-famous Kansas City-style barbecue, the question you have to ask yourself is which side of the tracks to visit.
We’ll answer that for you — both!

You see, Kansas City is mostly known for its bustling Missouri side, but we recently covered its namesake across the Kansas state line, which often flies under the radar
Whether you’re bringing the whole fam along, flying solo, or seeking a fun couples weekend getaway, KC ticks off every box with vibrant neighborhoods, sensational food, welcoming locals, and even a new Margaritaville hotel in Kansas, which is GoBankingRates claims is more affordable than Missouri.
Expect to budget for the following:
- Airfare for couple: $917
- Total hotel costs: $230
- Total meals: $417
- Total drinks: $57
- Total for entire vacation: $1,675

2) Saint Charles, Missouri: The Timeless Gem Of St. Louis
Say what you want about ‘The Lou’, whether it’s high crime rates or an array of free attractions, but outside the city limits lies Saint Charles, one of the Midwest’s most storied towns that feels like a film set.
Right now, with snowfall, it’s the perfect backdrop for a wintery Hallmark movie, but at the turn of spring and into summer, it becomes a lot more enjoyable to follow brick roads to downtown shops and savor wine bar patios.
Not to mention its prime real estate along the Missouri River makes for a great way to enjoy the outdoors with scenic parks and vibrant sunsets.

You can easily find an old-timey inn instead of a cookie cutter chain hotel. We love Boone’s Lick Trail Inn for a nostalgic stay steeped in centuries-old history.
Expect to budget for the following:
- Airfare couple: $881 (to STL presumably)
- Total hotel costs: $216
- Total meals: $375
- Total drinks: $45
- Total for entire vacation: $1,516
1) Cincinnati: The Former ‘Paris Of America’
Ohio may not be on your radar, but that’s not to say it shouldn’t be. With Cleveland, Columbus, and Cincinnati, it’s one of the most underrated Midwest states for a city break.

Whether you’ve heard the legend of skyline chili and want to give it a try to warm up this winter, or prefer to wait for sunny days ahead the following season, Cincy doesn’t disappoint.
While it doesn’t hold it’s former moniker of ‘Paris of America’ any longer, that doesn’t mean you can’t deep dive into history with its well-preserved streets of Over-the-Rhine and its preserved theaters and concert halls.
Split by the Ohio River just across from the Kentucky state line, Cincy is almost Kansas City 2.0 in that sense where you can double-dip 2 states in one trip if you’re a state counter.
Expect to budget for the following:
- Airfare for couple: $754
- Total hotel costs: $272
- Total meals: $360
- Total drinks: $49
- Total for entire vacation: $1,435
Subscribe To Our Latest Posts
Enter your email address to subscribe to Travel Off Path’s latest breaking travel news, straight to your inbox.
