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  • The Editorial Team

Midwest Weekend Getaway Road Trip


Photo from Wandawega


Looking for the perfect weekend getaway that is a quick road trip from Chicago? As Realtors in the Chicagoland area we often like to stay close to home in the event we need to get back to town for a quick showing on one of our listings. We have rounded up some of our favorite go-to destinations that are just a quick drive away. Pack your bags and load up the car with your favorite snacks!



1. Lake Geneva, Wisconsin

Broker Charlie Wood


Located an hour and a half north of Chicago, Lake Geneva has been a weekend destination since the late 19th century. Ever since the Gilded Age, it has been home to numerous lakefront mansions owned by wealthy Chicagoans as second homes, leading it to be nicknamed the "Newport of the West." There are plentiful things to do there, including lake boat tours, golfing at Grand Geneva, shopping in Lake Geneva's bustling downtown, disc golf (broker Charlie Wood's favorite), and hiking around the lake. Did you know the lakefront is public property so each lakefront home owner is required to maintain the path? This unique feature allows anyone to hike all the way around the lake in about 10 hours if one were so inclined while getting an up close and personal look at all the fantastic homes located there.


One of our clients recently bought a home that is available to rent in Abbey Springs, which is located on the Fontana side of the lake. While renting at Sandystone renters also have access to all of the amenities offered within Abbey Springs, a gated resort community. These amenities include an 18-hole golf course, indoor and outdoor pools, a fitness center, a game room, tennis courts, pickleball courts, basketball courts, volleyball courts, bocce ball courts, a playground, a restaurant and coffee shop, and a private beach, all a short drive away using the included golf cart.


Compass recently opened an office in the heart of downtown and you can explore some of the listings here.


2. South Haven, Michigan

The Fields of Michigan


2 hours northeast of Chicago, nestled along the shores of Lake Michigan is the quaint town of South Haven. In the early 1900s South Haven became a resort town, sometimes referred to as "The Catskills of the Midwest." One of the more unique stays in the Midwest is located at The Fields of Michigan. This resort is a return to life's simplest pleasures complete with a new spin on camping. Offering an authentic connection to nature combined with elevated luxuries brought to life by one-of-a-kind experiences, this stay is a must.



3. Elkhart Lake, Wisconsin

Camp Wandawega


Can't quite swing a trip to Switzerland this summer? Not to worry, just head 3 hours north of Chicago to the quaint little town of Elkhart Lake and stay at the Ostoff Resort. For a more rustic feel, opt for Camp Wandawega. From cabins to tree houses to luxury tents, this place drips with history and is like stepping into the past. The original tribe of the area, the Potowatomi, named the area Elkhart Lake because of the lake's resemblance to an elk's heart. It has also been long believed that the lake has curative powers. Legend has it If you bathed in the lake, you would be “rejuvenated and handsome again.” We're in!


4. New Buffalo, Michigan

The Thatch House


Consistently ranked as one of the best small towns in America, New Buffalo is located 70 miles or about 90 minutes from downtown Chicago and is at the gateway to 16 miles of sandy dunes along the Lake Michigan shoreline. New Buffalo boasts beautiful public beaches, a large harbor, independent shops and fine dining along with popular mainstays like The Stray Dog, and lots of recreational activities including Southwest Michigan’s first casino. One of our favorite places to stay is Nothin Dune, which is a short walk from downtown New Buffalo and located right on the water. If that popular home is booked, consider the amazing properties of Dwell Vacations which is where we are hosting the Olive Well retreat this year. Our team is pictured below at Dwell's Primrose property which we highly recommend. They have several properties in the broader area that are great for a big group getaway. Grab some friends and hit the road!

Team Olive Well at Primrose - a Dwell Vacations Home


Do you have a favorite road trip destination? Leave us a comment below, we are always looking for new places to go!








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