The Best Weekend Escapes from Chicago

Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, we’ve got you covered.

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While there’s plenty to do in Chicago, sometimes you need a weekend away from the hustle and bustle. Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, there are plenty of getaways surrounding Chicago where you can do just that—and they’re all within a five-hour drive. Blessed with the Great Lakes and many smaller, inland lakes, as well as rivers, chances are you will wake up by the water.

Getting away from the city, however, doesn’t mean losing access to culture. In fact, many of these small towns near Chicago thrive on fine dining, art and natural parks that will make you want to whip out your phone to capture the striking images. Be sure to pack hiking boots, too, to explore gorgeous trails, and sandals to walk on the beach or stroll around town. That this part of the Midwest isn’t super spread out also means you don’t need to drive very far for a weekend escape, which translates to spending less time in the car and more time enjoying your vacation.

Here are five destinations to check out, ensuring you come back to the city relaxed and reinvigorated. If a road trip is calling and you’re not sure where to go, this cheat sheet will help.

Visit Lake Geneva Lake Geneva.

Lake Geneva, Wisconsin

1.5-Hour Drive

Architecture geeks and The Gilded Age fans will love the grand, historic estates dating back to the late 1800s and early 1900s that surround Geneva Lake, accessible via a stroll around a section of the 26-mile Lake Shore Path or aboard a narrated Geneva Cruise Line boat tour. Dine with a lake view on the patio at Barrique Bistro & Wine Bar or linger over Italian-American food like wild-boar Bolognese pasta at Sopra Bistro on Main Street. Shop downtown for cheese curds and cheddars flavored with whiskey, dill and more at Hill Valley Dairy’s storefront, and poke into the Lake Geneva Public Library, designed by Frank Lloyd Wright protégé James Dresser and featuring stained-glass windows from Wright’s now-demolished Lake Geneva Hotel. For whimsical décor finds and entertaining frills, head to the other side of the lake to Fontana Home. The best design-oriented spot for a beer is at Topsy Turvy Brewery, within a 1910 former church.

Visit Lake Geneva Grand Geneva Resort.

Where to Stay

Featuring an outdoor pool with striped umbrellas and a speakeasy-style bar, Maxwell Mansion’s 28 rooms are divided between the main house and former horse stables. For a full-service experience that includes a spa, steakhouse, Italian restaurant and outdoor pool, try the Grand Geneva Resort & Spa, whose interconnected buildings were once home to the Playboy Club. Today, you can sip cocktails in the lobby’s sunken lounge.

Modales Modales Vineyard.

Saugatuck, Michigan

2.5-Hour Drive

Hugging Lake Michigan’s western shoreline, Saugatuck, fittingly known as “The Art Coast,” is home to dozens of galleries. Most are sprinkled downtown near shops and restaurants, although the two-story, 12,000-square-foot J. Petter Galleries just outside of town is worth a trip, and hosts a wine bar within. In nearby Douglas, one of the nation’s oldest artist residencies—Ox-Bow, affiliated with the School of the Art Institute of Chicago, also a destination for art and writing classes—hosts an art gallery and boutique (Ox-Bow House) in an adorable white church dating back 152 years. Modales Wines in Fennville pours wines crafted by its Napa Valley-born winemaker, formerly of Duckhorn. Explore further on a vertical hike down sand dunes at Opal Beach, or rent a 1950s electric boat from Retro Boat Rentals to cruise along the Kalamazoo River to live our your IRL Emily Henry novel dreams.

Stoffer Photography Wickwood Inn.

Where to Stay

Owned by Chicago design firm Soucie Horner, the 11-room Wickwood Inn is a new, modern revamp of The Silver Palate Cookbook author Julee Rosso’s inn. Rosso also owned a gourmet-foods shop of the same name in New York City. Antiques and artwork tie into a clear coastal vibe that includes outdoor s’mores and French bistro chairs on the patio.

Kohler Co. The Immigrant Restaurant.

Kohler, Wisconsin

2.5-Hour Drive

This company village town—nearly everyone works for the luxury plumbing manufacturer—also excels at hospitality. The Immigrant Restaurant has long been considered one of Wisconsin’s best fine-dining restaurants; it embraces early-American art and décor while serving a five-course tasting menu, plus delicacies like caviar and 16 artisan Wisconsin cheeses. At the three-level, 36,000-square-foot Kohler Design Center, rooms by celebrity designers can be toured and the design staff is available to chat. Then, at Kohler Waters Spa, hydrotherapy treatments incorporate Kohler’s Vichy shower. On your way into town, swing by Art Preserve, a museum dedicated to artist-built environments by folk artists. Tours of the Kohler factory across the street from the hotel are led by retired employees.

Kohler Co. The Eau de Vie Suite at the American Club.

Where to Stay

The American Club is the most luxurious of the three Kohler properties, with 241 rooms. Built in 1918 for single male immigrant employees, it’s now one of Wisconsin’s most coveted properties, with a spa, yoga studio, multiple restaurants, golf courses and shops all within a short walk and managed by the resort.

Galena Country Tourism Galena, Illinois.

Galena, Illinois

3-Hour Drive

Situated along the Mississippi River, Galena boasts an adorable downtown dotted with antiques stores (like the 200-some vendors at Elizabeth’s Grand Antique Co. in a former school) and unique boutiques along Main Street. That includes Galena Apothecary (formerly of Chicago, the owner opened the shop in her favorite weekend-getaway town), Galena Book & Paper (books and stationery) and Galena River Goods (candles, skincare products, barware and clothing). Sip bubbles in Champagne on Main’s outdoor courtyard and choose your dinner spot after a walking tour with Galena Foodie Adventures, visiting five different eateries.

Galena Country Tourism Goldmoor Inn.

Where to Stay

Tuck in at night at Goldmoor Inn, a castle-like structure just outside of town with 13 suites and breakfast included. Massages are also available on-site, in the inn’s dedicated spa room, including a hot-stone massage to work out the kinks.

Traverse City Tourism Sleeping Bear Dunes, Traverse City, Michigan.

Traverse City, Michigan

5-Hour Drive

This emerging wine region is also a great spot to hike; make sure to take in the soaring bluffs at Sleeping Bear Dunes National Lakeshore and to sail. The Wind Dancer, offers sunset sails nearly daily as well as Champagne Sails on Sunday afternoons. Short on time but still want to experience a local winery? Head to the 155-acre Brys Estate Vineyard & Winery, where the vineyard views from an elevated deck are nothing short of picturesque, with vistas of a lavender field and gardens blooming with flowers and herbs. The winery also serves frosé, plus cheese and charcuterie boards. Perusing downtown Traverse City’s shops, including two bookstores, can easily fill an afternoon. History buffs will love Trattoria Stella’s cave-like environment, located at The Village at Grand Traverse Commons, a former state-run mental hospital with a philosophy that a beautiful environment is healing.

Delamar Traverse City Delamar Traverse City.

Where to Stay

 Delamar Traverse City’s perch above the West Arm of Grand Traverse Bay means water views for days and the on-site yoga studio puts wellness within easy reach, plus a restaurant wildly popular with locals. Or, wake up next to the grapes at the 10-room Inn at Black Star Farms, which also hosts private yoga classes in its vineyard.

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