These Are The Midwest’s 4 Most Beautiful Getaways With No Crowds

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We all know how amazing Chicago is from its blue-water shores, towering luxe hotels, and array of vibrant neighborhoods in the Midwest’s sole metropolis.

But there are many other places to discover if massive cities aren’t your jam.

The Midwest can often be misrepresented. It’s not a boring hellscape with never-ending corn fields like cheesy road-trip movies portray.

Cities like St. Louis and Indianapolis are 2 of my personal favorites that will wow you as underrated getaways, but I’m not playing tour guide today.

Today, we’re handing the keys to the expert team at Midwest Living, who obviously focus on this sprawling region of the U.S. day in and day out.

Their latest piece revealed 25 of the Midwest’s top gems. We handpicked 4 that we feel are not only beautiful, but ones that many tourists skip, ultimately making your visit more authentic and virtually crowd-free.

1) Indiana Dunes: The Prettiest Shores You’ve Never Heard Of

Not to switch to the South, but George Strait once sang about ‘oceanfront property in Arizona’, which is obviously a song about stretching the truth.

We’re not trying to trick you — as hard as it may be to believe, Indiana has beautiful beaches.

Whether you’re one of many visiting recording-breaking Indy or shoving Portillo’s hot dogs down your gullet in the “Windy City”, Indiana Dunes National Park makes a gorgeous spring and summer trip to enjoy the beauty of Lake Michigan.

To be exact, there are 3 miles of coastline along America’s most sought-after lake as it exudes shades of the Caribbean.

Our one piece of advice: If you rent a car, try to score an Indiana plate for the in-state entry rate of $7, otherwise it more than doubles to $15 for out-of-staters.

2) Madison: One Of America’s Most Underrated Capitals

If you’ve flirted with a trip to Madison before, it’s likely been for one of a pair of reasons:

College football or Wisconsin’s renowned fall foliage.

But those are too far off to think about right now.

Madison is a 3-season destination and the first of those 3 is right around the corner.

Since many of Madison’s tourism derives from a fall influx, spring is the perfect time to visit ample museums, one of 600+ restaurants, and take in the waterfront scenery backdropped by a staggering Capitol.

This city is largely considered safe and affordable too, but what makes Madison truly one-of-a-kind is the fact that its postcard cityscape is sandwiched by 2 different lakes, Lake Mendota and Lake Monona.

3) Milwaukee: Sore Reputation Deters Tourists From Waterfront Delights

You hardly hear of anyone vacationing in Milwaukee, with Chicago being so close and more accessible.

But let’s not look over the fact that this city with the claim to fame of its booming beer scene resides on the very same vivid shoreline that Chicago does, except it’s mostly locals who pour in to enjoy it.

Of course, we’d be remiss not to mention the fact that Milwaukee doesn’t exactly have the best reputation.

But downtown tells a very different story — scenic waterfronts, lively public spaces, and revitalized neighborhoods.

In other words, Milwaukee is one of those cities people love to misjudge.

The sore spot is its crime levels. Milwaukee came in 24th in U.S. News & World Report’s annual ‘most dangerous’ list.

4) Fox Valley: Discover Illinois’ Charming Side

Chicago may steal the spotlight, but Illinois’ Fox Valley is where travelers find charming towns, blissful beauty, and not a crowd in sight.

You’ll find riverfront charm everywhere as the Fox River pierces through multiple towns packed with walkable townscapes fit for a Hallmark film set.

Not to shove it in Midwest Living’s face, but we scoured the map and picked 4 towns we truly believe you’ll love at first sight:

Oswego: a peaceful retreat where leafy parks, river views, and wide-open trails
Geneva: an upscale (yet laid-back) escape with Third Street’s boutiques, cafes, and wine bars
Batavia: a relaxed riverfront town with the Fox River Trail and the area’s best craft brewery clusters
St. Charles: the liveliest of the bunch; historic downtown, Riverwalk, and buzzing live music scene

Sam Sears

Sam, our Lead Writer & Journalist based in San Diego has visited 36 countries and written over 1000 articles with a focus on sharing his own travel experiences and shining a light on lesser-known gems.