Chicago is an incredible summer destination in and of itself: miles of lakefront beaches, dozens of lake and river cruises, and all the outdoor arts and culture one has time for. But just outside the city are a handful of reasons to pack up the car and hit the road. From a stunning Five-Star hotel and spa destination to a picturesque peninsula on Lake Michigan, here are our favorite weekend getaways from Chicago.
Madison, Wisconsin
A university town located at the crossroads of two stunning lakes, Wisconsin’s capital is a lush, green retreat just two-and-a-half hours northwest of Chicago. With 6,000 acres of parkland and the vast University of Wisconsin Arboretum, the city is overrun with scenic trails ideal for biking and hiking. But it also has great dining spots and the must-visit Saturday farmers market on Capitol Hill. Consider foregoing the usual big-hotel lodging in favor of accommodations that best suit this lovely Midwestern town: the traditional B&B. We had a lovely experience at the modern Arbor House, An Environmental Inn, and we plan to give The Speckled Hen Inn a try next time.
Three Oaks, Michigan
With fewer than 2,000 residents, the tiny village of Three Oaks, Michigan, is an hour-and-a-half drive from Chicago and offers more than its fair share of culture. Among the reasons we love visiting are the gorgeous Acorn Theater, which hosts live events (everything from concerts to plays) several nights a week, and the Journeyman Distillery, which makes some of our favorite Midwestern spirits. Stop for a luncheon at the pretty Viola Café or the popular Froehlich’s bakery and deli. A handful of galleries (Blue Gallery, Studio b.) make the hour-long jaunt worthwhile for both day trips and overnights, with the caveat that lodging in Three Oaks is limited to just a few B&Bs. Instead, treat yourself to a sleek apartment-like room at Marina Grand Resort in nearby New Buffalo, or the waterfront Harbor Grand Hotel, where you can top off your stay with a massage.
Kohler, Wisconsin
A charming hamlet an hour north of Milwaukee, Kohler was founded as a workers’ village for the famed plumbing company, and has since been transformed into a Forbes Travel Guide Five-Star hotel and spa. The American Club boasts luxury accommodations and Four-Star dining (at the superlative Immigrant Restaurant) set in the village’s historic brick dormitory. The adjacent and recently renovated Carriage House is home to the Five-Star Kohler Waters Spa, where (naturally) water therapy is a highlight of the spa menu. The resort’s championship golf courses have played host to dozens of pro tournaments, and in the summer, offer the closest thing you’ll find to Scottish links-style play east of the Mississippi.
Lake Geneva, Wisconsin
When Chicagoans tire of Lake Michigan, they head to this picturesque lake destination that’s an easy 90-minute drive across the Wisconsin border. Upscale resorts are commonplace in this stunning city-dwellers’ getaway, and family-friendly dining and activities are easy to book well in advance. Both Geneva Ridge Resort and Grand Geneva Resort & Spa are longtime favorites for families and couples, but the elegant Baker House, a recently restored 1885 manse, harkens back to a bygone era of lake house luxury and is a good pick if you want to dig into local history.
Door County, Wisconsin
While Door County is a longer trek — about four hours from downtown Chicago — it’s easy to see why so many Chicagoans find themselves splashing on the shoreline here every summer. With more than a dozen little towns and villages strung along about 50 miles of this pretty peninsula, Door County is a mecca for lighthouses, B&Bs (The Chanticleer Guest House, Ephraim Inn) and beaches. Driving is a must and has its rewards: Travel to the tip of the peninsula and hop the car ferry to Washington Island, where Icelandic and Swedish heritages are celebrated through rare-breed pony farms (check out Norse Horse Park) and delicious crêpe-like Icelandic pancakes with fresh fruit at Sunset Resort.
