Weekend Road Trips from Chicago: Explore South Haven, Kohler and Mackinac Island

South Haven, MI

South Haven is a classic beach town that offers the perfect mix of relaxation and adventure. Just a little over two hours from Chicago, it’s an ideal destination for independent travelers seeking a quiet retreat, couples craving a romantic getaway and families looking for fun in the sun.
Things to do in South Haven:

• Pick Your Own Fruit — You can pick blueberries at DeGrandchamp Farms or head to Overheiser Orchards for cherries, peaches and pears.

• Hit the Links – Beeches Golf Club and Hawkshead are both a few minutes from downtown, with driving ranges and options to play nine or 18 holes.

• Relax on the Beach – South Haven’s shoreline is perfect for long walks, building sand castles or simply soaking up the sun. Spend your afternoon at either North Beach or South Beach, both offering easy lake-access, picnic areas and beautiful views.

• Hit the Trail — Walkers or cyclists head out on the Kal-Haven Trail, which stretches for 33 flat and gentle miles through woodlands, farmland and countryside from South Haven to Kalamazoo.

• Set Sail at Sunset — End your day with a sunset cruise on Lake Michigan. Local tour operators offer evening sails that provide a unique perspective on South Haven’s iconic lighthouse.

Kohler, WI

Kohler, Wisconsin offers a refined escape where history, luxury and wellness intersect. Best known for its world-class spa, championship golf courses and iconic hospitality, Kohler is the perfect weekend getaway for couples seeking relaxation, history buffs interested in local heritage and travelers looking for a touch of indulgence.
Things to do in Kohler:

• Indulge at the Spa — the town is perhaps best known for the Kohler Waters Spa. While in recent years locations have cropped up in Chicago and around, the Kohler location is the flagship and most inviting.

• Factory & Design Studio — For those interested in the craftsmanship behind Kohler’s world-renowned plumbing fixtures, the Kohler Factory Tour offers a behind-the-scenes look at the company’s innovation and manufacturing process. While tours are offered on a limited basis, the Design Center is open daily and showcases both Kohler history and products.

• World-Class Golf — Kohler is a serious golf destination, and enthusiasts can tee off at Whistling Straits, which has hosted four major championships and the Ryder Cup, or Blackwolf Run.

Mackinac Island, MI

For a truly unique weekend getaway, Mackinac Island offers a charming escape where the pace of life slows down, and the past feels wonderfully present. Mackinac Island is located on Lake Huron, between Michigan’s Upper and Lower Peninsula, it is best known for its car-free streets, where visitors explore by horse-drawn carriage, bicycle or on foot. It is a great destination for couples, families and independent travelers eager to slow down for a weekend.
Things to do in Mackinac Island:

• With no cars allowed on the island, biking is one of the best ways to take in the breathtaking scenery. The 8.2-mile perimeter trail around the island offers views of Lake Huron and passes through scenic stretches of forest, charming cottages and iconic landmarks like Arch Rock.

• Fort Mackinac, a well-preserved 18th-century military outpost that played a pivotal role in the War of 1812, is home to Michigan’s oldest building. Exhibits and live reenactments bring the island’s history to life, with self-guided or group tours available.

• You can take a carriage tour of the island, and also visit the Grand Hotel’s stables and carriage museum. The museum houses 30 antique carriages and sleighs, including those used by dignitaries and celebrities.

• Little kids — and big kids - may enjoy the Mackinac Island Butterfly House. They can walk through hundreds of vibrant butterflies fluttering around lush tropical gardens.

South Haven, MI

• No visit to South Haven is complete without ice cream, and there are lots of places to choose from! We’re partial to Kilwin’s on Phoenix Street.

• For a laid-back vibe, have a cold beer and some fried fish with the locals on the dock at Captain Lou’s. It’s the perfect place to unwind, listen to live music and watch the boats come and go along the river after a day of exploring.

• Taste offers a long list of small plates and creative martinis. They also operate Chomp, a take-out window around the corner, for hot dogs and drinks.

Kohler, WI

• For a sweet treat, visit Kohler Chocolates at the Shops at Woodlake, for a selection of handcrafted chocolates, truffles and the famous Terrapins — Kohler’s take on the classic turtle candy.

• The Horse & Plow, located on the lower level of The American Club, is a family-friendly casual gastropub offering classic Midwestern comfort food and local craft beers.

• Taverne on Woodlake is a casual, family-friendly lunch and dinner spot with a farm-to-table menu of sandwiches, entrees and pizzas.

• The Immigrant Restaurant is Kohler’s fine-dining restaurant inspired by the heritage of the immigrants who shaped Kohler. The menu blends European influences with locally sourced ingredients, in a candlelit setting – perfect atmosphere for a romantic dinner or celebratory meal.

Mackinac Island

• Mackinac Island fudge is delicious and ubiquitous on the island. Walk along Main Street and pop into one of the many fudge shops to try a piece or pick up a souvenir box to gift or bring home.

• The Jockey Club combines a stone fireplace, cozy leather booths and unique artwork with a fresh, elevated American menu. This is Marc’s favorite restaurant on the island.

• Each night, the Main Dining Room at the Grand Hotel hosts five-course dinners, ending with the hotel’s famous Grand Pecan Ball. Dinner here is an event, with jackets and ties required for men, and dresses, skirts, dress pants, etc. for women.