Anywhere but Here: Three Quick Winter Getaways from Sweet Home Chicago

  • Bridget Chambers
  • 02/8/22

Got cabin fever? While February universally conjures feelings of love and connection… Chicago weather can evoke anything but. The story of mid-winter in the Midwest usually begins with complaining, peaks with snow blowing and driveway shoveling, and ends with a defeated feeling and the yearning get out of dodge. Making a haven of your home helps to make the winter bearable, but what happens when that’s not quite enough? 
 
Leaving home for a trip – even a quick one – can come along with logistics that feel too daunting to tackle in the midst of the winter blues. Maybe there’s a simpler way. Perhaps this year, you can allow winter to inspire your inner wanderlust. 
 
On that note, we’ve rounded up the best quick jaunts (three hours or less!) from Chicago to help you conquer your winter slump:
 
Go Back in Time
Kohler, Wisconsin ~ 149 miles from city limits
 
Sometimes just crossing state lines can put a pep in your step. This serene, special Wisconsin town does much better than that… and offers more than cheese and Packers. :) 
 
If the name sounds familiar, it’s because you’ve seen the Kohler name plastered on bathroom fixtures across America. Yep, it’s that Kohler! In about 2.5 hours, vacation-seeking visitors can visit a world-class spa (chock-full of amenities like an indoor whirlpool and waterfall, a rooftop fireplace, and over fifty treatment offerings), indulge in a breathtaking outdoor landscape, and enjoy lodging fit for a storybook. This quaint village in Sheboygan County offers three different lodging levels – cabins, spa suites, and hotel rooms – and is famous for its hospitality star, The American Club. Their legacy of incomparable hospitality has earned The American Club a coveted Five-Diamond distinction from AAA and a Forbes Five Star rating. Guests can enjoy a respite from their phones to enjoy board games by the fire, free daily teatime and scones, and succulent feasts at the hotel’s culinary masterpiece, The Immigrant Room. 
 
If this winter destination leaves you wanting more, Kohler offers incredible summer activities – not the least of which are two championship golf courses that have hosted the PGA Tournament and the 2021 Ryder Cup. Tiger Woods is a regular visitor!
 
 
The Path Less Traveled By
Union Pier, Michigan ~ 74 miles from city limits
 
A little less well-known than its neighbors New Buffalo and Saint Joseph, this sleepy Michigan town is the Midwest’s best kept secret. Union Pier is situated on the southwest corner of Michigan, hugged by wineries and eateries galore. (It’s so special, in fact, it was voted one of the top 50 places to travel this year by Travel + Leisure.)
 
In less than 1.5 hours, weary travelers can find themselves energized by a community less densely populated by tourists. Here, you can grab a glass of wine and put your feet up. Visitors relish in the view of the Lake Michigan coastline and sunset – perfect for a family getaway, a romantic escape, or group of friends looking to reconnect. Walking paths line the lakeshore, free-of-charge bookstands sit on street corners, and people wave to one another. In a nutshell, Union Pier feels like The Hamptons… with a much more reasonable price tag. 
 
Our best bets for stuff to do? Foodies can grab mouthwatering Asian food and live music at Timothy’s Place, delectable seafood and steaks at Frankie’s, or a roadside burger at Red Arrow. Those visitors seeking splendid accommodations can try the nearby Inn at Union Pier, but most prefer to check out cozy rentals on VRBO. Those with a penchant for shopping won’t be disappointed either…antiques are the name of the game, and the selection of treasures is second to none. 
 
No matter what you choose, one fact is certain: Making Michigan your home-away-from-home is your ticket to a more jovial winter.
 
Stay in the State
Galena, IL ~ 164 miles from city limits
 
Known for its preserved 19th century charm, architecture, and history, Galena is a town very worth a visit. Since it’s situated in the northeastern part of Illinois – and a bit far from any great lakes – Galena is a place that gets less press than other nearby vacation locales. However, travelers looking for a change of pace would benefit from giving Galena a go.
 
Galena’s most attractive winter endeavor can be found at Chestnut Mountain Resort, Illinois’ only ski-ready mountain. Guests can warm up with hot cocoa and then hit the slopes morning, noon, and night. Folks looking for a less athletic escape will find respite in the myriad shops, spa, and eateries sprinkled across the Galena Historic District downtown. Cobblestone streets set the tone for a traditional town rooted in Illinois history – where 18th U.S. president Ulysses S. Grant once called home. (History buffs will be glad to know they can take a tour of his 1865 house.) 
 
Local vineyards are backdropped by the Mississippi River Valley, where regular tours and tastings can be booked all year long at places like Massbach Ridge Winery. Happy hour is every hour, here, too. Weekends often offer restaurant discounts (try 50% wine bottles every Friday at Fried Green Tomatoes), and good food is abounding. Log Cabin Steakhouse is a local favorite, and caffeine aficionados will satisfy coffee cravings at Galena Roasters.
 
A far cry from the beautiful chaos of home, Galena is Chicago’s quiet but spunky counterpart.
 
POV: Anywhere but here
Even the most dedicated homebodies need a little change every once in a while. Summer vacations are a bit easier, sure. But winter can set the scene for a perfect weekend detour. 

Sometimes, leaving home makes you appreciate where you come from. Sometimes, a short time spent away from family and friends can shine light on their incredible importance in your life. Sometimes, experiencing something other than home can give home its value. And sometimes, life just feels better when you allow yourself to see it from another point of view.
 
And when you do make your way back home, make a quick call to real estate partners Sophia Klopas and Jason Stratton. They can help you find a place that feels like vacay 365 days a year.


Catch us back here bi-weekly as we bring you curated and Chicago-based real estate content (with a life coach’s twist).

 
 

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Partners Sophia Klopas and Jason Stratton are a brother and sister team who have been in the Illinois real estate market for over twenty years. Together they offer complementary skill sets and professional expertise that make KlopasStratton truly unique.

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