Three Spring and Summer Driving Getaways from Chicago
When the weather warms up and the days get longer, it’s the perfect time to escape Chicago and head out for a weekend getaway. Within just a few hours, you can find yourself lounging on a quiet beach, exploring charming small towns, or immersing yourself in outdoor adventures.
This guide highlights three weekend driving getaways from Chicago—each offering something unique for spring and summer travelers. South Haven, Michigan draws visitors with its Lake Michigan shoreline and charming downtown. Kohler, Wisconsin blends luxury, wellness, and the outdoors in a sophisticated resort setting. And for those seeking a step back in time, Mackinac Island offers an unforgettable experience where horse-drawn carriages replace cars.
Below are details on why these destinations are perfect for a 2 or 3 night spring or summer weekend escape, what to do while you’re there, and where to stay for an unforgettable getaway. For those not from Chicagoland, these destinations could be combined with a summer trip to the city to add on a couple of days and a different experience.
We love weekend getaways, and are happy to help build your trip to these destinations or others. Reach out to us here or at hello@keytraveladvisors.com if we could help you getaway for a weekend this spring or summer.
South Haven, Michigan (2 hrs)
Along the eastern shore of Lake Michigan, South Haven is a classic beach town that offers the perfect mix of relaxation and adventure. The summer calendar is South Haven is packed, with a variety of fairs, festivals, and holiday events. 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.
What to do:
Pick Your Own Fruit – You can pick blueberries at DeGrandchamp Farms or head to Overheiser Orchards for cherries, peaches, and pears. These family-friendly farms offer u-pick and pre-picked fruit. Overheiser also has a goat and llama feeding zone and a kids play area.
Hit the Links – Beeches Golf Club and Hawkshead are both a few minutes from downtown, with driving ranges and options to play 9 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.
Where to eat and drink:
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.
Where to stay: South Haven has a variety of accommodation options including bed and breakfasts by the beach, downtown hotels like the Old Harbor Inn, and condo or home rentals suitable for families or groups.
Kohler, Wisconsin (2 hrs 30 min)
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.
The village of Kohler was founded in the early 1900s by John Michael Kohler, whose vision was to create a model company town where factory workers could live and thrive. At the heart of this vision was The American Club, a red-brick Tudor-style building originally built in 1918 as a dormitory for immigrant factory workers at the nearby Kohler Co. plant. Today, The American Club has been transformed into a five-star resort, blending its rich history with modern elegance.
What to do:
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.
Where to eat and drink:
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 in 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.
Where to stay:
The American Club is both a historic and luxury property with elegant rooms, five-star service, and close access to Kohler’s activities. Staying here offers not only comfort and sophistication but also a connection to Kohler’s rich heritage.
The Inn on Woodlake is also managed by Kohler, sits close-by, and offers contemporary design at a lower pricepoint.
Mackinac Island, Michigan (5 hrs 30 mins)
For a truly unique weekend getaway, Mackinac Island offers a charming escape where the pace of life slows down, the past feels wonderfully present, and the character and culture contribute to a strong sense of place. Located in Lake Huron, between Michigan’s Upper and Lower Peninsulas, Mackinac Island 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.
What to do:
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 could take a carriage tour of the island, and you could also visit the Grand Hotel’s stables and carriage museum, which 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 where they can walk through hundreds of vibrant butterflies flutter around lush tropical gardens.
Where to eat and drink:
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 an 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.
Where to stay:
The Grand Hotel – Stepping into The Grand Hotel feels like stepping back in time. Opened in 1887, this iconic resort is known for its historic elegance, period-designed rooms, timeless traditions, and the longest porch in the world – the only place you could enjoy this hyper-micro-brew.
The Inn at Stonecliffe offers a more intimate stay. The Inn was originally built as a summer cottage in 1904, and offers traditional rooms in the mansion or more contemporary suites at the Summer House – all while enjoying serene surroundings and lake views.
