5 Drives From Chicago for Friends, Families, Couples and Solo Travelers

Sep 1, 2018

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As part of a series on long weekend getaways, we’re showing you how to make the most of your summer Fridays, school breaks and the season’s extra-long days. Check back every week for inspired itineraries and easy city escapes. 

Chicago has a lot to offer within city limits, but it’s easy to forget how much awaits just a few hours away. Adventure-seekers can fly down a 335-foot-long waterslide, careen through creeks on an ATV tour and soar with the birds on a hot air balloon ride. For people who travel to relax and rewind, there’s a private cabin on 350 acres in northern Wisconsin. And active travelers will find plenty of cycling paths and hiking trails, including ones that navigate a series of sandstone canyons in an Illinois state park. History buffs, meanwhile, can delight in seeing the former home of President Ulysses S. Grant, still decorated with its original furnishings, in small-town Illinois.

No matter what kind of traveler you consider yourself or where you go on a long weekend getaway from Chicago, you can find excellent food and drinks, be it the cheese curds in Wisconsin or taproom fare on a crawl of southwest Michigan’s breweries, distilleries and wineries.

Best of all, it’s all within 200 miles of the city; perfect for a long weekend or even a mid-week jaunt.

Kohler, Wisconsin 

Distance from Chicago: About 150 miles (2.5-hour drive)

The family behind the Kohler Kitchen + Bath company — the name you see on penthouse-worthy showers and soaking tubs — runs a resort called Destination Kohler, where accommodations feature the most beautiful bathrooms you’ve ever seen. If you do muster up the willpower to leave your personal rain shower, a charming campus of indoor and outdoor activities awaits, highlighted by a quartet of championship golf courses and a spa offering hydrotherapy treatments.

What to do: Book a waterfall massage or acoustic bath at Kohler Waters Spa; hike and trapshoot at River Wildlife, a 500-acre wilderness preserve; and browse clothing stores and more at the Shops at Woodlake, an outdoor mall that’s a short walk from the spa. Golf courses include Whistling Straits, home to the upcoming 2020 Ryder Cup. Bold Cycle, which opened in May, is a 3,000-square-foot cycling studio with 35 sleek Stages bikes. Also new: the Journey package, which pairs you with a “wellness concierge” who will help you plan your itinerary around unplugging from tech, mindfulness and meditation, or healthy diet and exercise. Slot in time to explore the Kohler Design Center, a showroom of model kitchens and bathrooms where showers change colors and bathtubs mimic infinity pools.

Where to stay: Rated a five-diamond property by AAA, The American Club — an ivy-clad brick building that feels more like a private mansion than a hotel — is the crown jewel of the property. There’s also the Carriage House, which has the perk of being attached to the spa (head from your room to breakfast to your massage without taking off your robe and slippers), and the Inn on Woodlake, recently expanded to add more multi-bedroom suites for families and groups of friends. All are available on Hotels.com, so be sure to use the Capital One Venture Rewards Credit Card and book at Hotels.com/Venture to get 10x miles on your stay. Remember that the Hotels.com Rewards program gets you one free night for every 10 paid nights you stay, effectively boosting your return to 20% when you pay with the Venture card.

What to eat and drink: The Horse & Plow, the casual restaurant and bar at The American Club, has some of the best food on property, including a strong contender for the best cheese curds in all of Wisconsin. Try braised elk at Blackwolf Run Restaurant, which has a wine list that has been honored by Wine Spectator every year since 2002 — and a terrace overlooking the 18th-hole greens of Blackwolf, a Pete Dye-designed golf course. For lunch, Craverie Chocolatier Cafe is the spot for salads, sandwiches and gleaming glass cases lined with chocolate truffles, terrapins and toffee bark, made on-property by a resident chocolatier.

Starved Rock State Park, Illinois 

Distance from Chicago: About 95 miles (2-hour drive) 

The tall bluffs at Starved Rock are a stunning sight in an otherwise flat state, and a destination for hikers looking for terrain to scale. The park’s topography was formed thousands of years ago, when melting glaciers eroded everything in in the area except the resistant St. Peter sandstone. Today, steep sandstone walls create a series of 18 canyons that, after a heavy rainfall, act as natural waterfalls.

What to do: Hike! There are 13 miles of trails to explore, appropriate for all skills levels, with 14 potential waterfall sites among the 18 canyons. Grab a map from the Starved Rock Visitor Center, or take a 75-minute free guided hike, departing from the visitor center at 9:30am on Saturdays through Nov. 17. A new river boat, The Eagle 1, offers tours down the Illinois River four times a week through the end of September. In the winter, hike in search of icefalls, created when the waterfalls freeze into ice formations along the canyon walls. Animal lovers can drive 15 minutes to Cedar Creek Ranch for guided horseback rides through nearby trails, a petting zoo and ATV tours.

Where to stay: Starved Rock Lodge, the only hotel in the park, has a main building with 69 rooms, but more fun is renting one of the lodge’s five Pioneer Cabins, tucked in the woods (but still, for better or worse, a short walk to civilization). If you want the true outdoor experience, try pitching a tent in one of Starved Rock’s 33 campsites, outfitted with electricity and near a bath house with toilets and showers. (Most sites have a 30-amp camper hookup; a limited number have a 50-amp travel-trailer hookup.)

What to eat and drink: Located at Starved Rock Lodge, Back Door Lounge has a new seating area and new furniture on its patio, known as the Veranda. Settle in with the gorgonzola nachos or a pepperoni flatbread and watch out for Oktoberfest dinners in late October. The lodge’s new mid-week Hops & Hideaway package sends craft beer lovers to neighboring town Ottawa with a $50 voucher for Tangled Roots Brewing Company. Also in Ottawa, Hank’s Farm Restaurant, open since 1941, is a converted dairy barn where fried chicken and baby back ribs share the menu with spaghetti, ravioli and chicken parm.

Southwest Michigan  

Distance from Chicago: About 85 miles (2-hour drive)

Live in Chicago long enough and you will get invited to a bachelorette party planned around the pocket of wineries in the southwest corner of Michigan. Less talked about, but arguably better: the area’s breweries and distilleries. There are a handful of towns you can stay in to accomplish this tour de drink, some tucked flush against Lake Michigan and others slightly inward.

What to do: Make this a 21-and-up trip, and here’s your holy trinity: Journeyman Distillery, purveyor of nine varieties of whiskey; Round Barn, which does wine, beer and spirits in a circular white barn built in 1912; and Tapistry Brewing, with a sunny beer garden and 20 taps pouring everything from a rye pale ale to limited-release double IPA Heart Full of Napalm. Of course, once there, you can’t not walk across the street to Transient Artisan Ales to try The Shepard, an oak-aged sour with blueberry and black currant or Spirit Spring, a beer-cider hybrid aged in apple brandy barrels. (You’ll need a designated driver, or you can rely on Uber.) Save one day for a bike adventure on a network of paved bike paths called Backroads Bikeways, which takes cyclers through up to 60 miles of gorgeous nature. 

Where to stay: Neighboring resorts The Harbor Grand and Marina Grand in New Buffalo, Michigan are a 15-minute drive from Journeyman. The Inn at Harbor Shores in St. Joseph, Michigan is further north — a 20-minute drive from both breweries— but the spa, golf course, kayak rentals and sand volleyball make it a solid spot to spend a few nights. This is also an excellent area to find an Airbnb. If you opt for the later, put the purchase on your Chase Sapphire Reserve for 3x points.

What to eat and drink: Fuel up at any of your drink stops: Journeyman has a restaurant called Staymaker, home to dishes that incorporate its spirits (a charcuterie board with bourbon mustard, Detroit-style pizza with crust made from the whiskey grain mash bill used in the Last Feather Rye); Round Barn has Public House at its actual brewery, just three miles from the tasting barn; and Tapistry has a menu of sandwiches and apps, including smoked cheddar beer cheese served with pita bread.

Wisconsin Dells, Wisconsin

Distance from Chicago: About 200 miles (3.5-hour drive)

The Dells is famous for Noah’s Ark, a 70-acre waterpark that earns the title of largest in America, but the family-focused vacation town also offers a main drag filled with restaurants, shopping and mini golf; and camping, ropes courses, spas and wineries within a 15-minute drive.

What to do: New for 2018 among more than 50 rides and slides at Noah’s Ark is a king cobra-shaped waterslide called Raja with a daunting 335 feet of track that takes you up to 32 miles per hour, ending in a 37-foot drop. Towel off and explore the rest of the Dells, including the year-old Bigfoot Ropes Course and new VR Universe, an arcade of virtual-reality games. Escape rooms, where you tackle a series of clues to find your way out, are hot, with DOA Room Escape at the Wilderness on the Lake resort and Wrath of Anubis, an Egyptian-themed escape room just added to the Kalahari resort. Old standbys include the Haunted Mansion haunted house, Tommy Bartlett Show of boat and water-ski stunts and Capone’s old-time portrait studio in Downtown Dells.

Where to stay: Adults-only Sundara Inn & Spa is doubling in size with a $13 million expansion that includes a rooftop greenhouse, glass-walled meditation room and miles of hiking trails. For kids, Kalahari is a family favorite thanks to its two waterparks — one indoor, one outdoor — and indoor theme park boasting a Ferris wheel, carousel, climbing wall, go-karts, laser tag and mini golf.

What to eat and drink: The sugar-sprinkled doughnuts and Friday fish fry at Paul Bunyan’s Cook Shanty in Downtown Dells, a log-cabin restaurant guarded by a towering lumberjack statue, is a tradition for many a family, but there’s plenty of new food and drink to try in the Dells, too. Mid-April through October, head to the 50-person patio at the new Prairie Hawk Winery, a family-owned business that makes chardonnay, riesling and rosé with imported grapes, plus hard cider with local apples. Drinkers should also hit Wollersheim Winery & Distillery, which released its first rye whiskey in February. Boats can dock right at Summer House Grill & Bar, a new restaurant on Lake Delton with a focus on local ingredients. And for a proper Wisconsin supper club experience, prime rib and brandy old-fashioned included, visit Ishnala Supper Club, which just added a new bar and lounge area on its lower floor.

Galena, Illinois 

Distance from Chicago: About 165 miles (3-hour drive)

In the 1830s, Galena was the picture of small-town America, home to a vital trading post on the Fevre River and a thriving Main Street alive with carriages and foot traffic. Today, with its well-preserved 19th-century buildings, the town is a destination for history buffs and architecture fans — but with new restaurants, spas and B&Bs peppering the area, a trip here is definitely not just about the past.

What to do: Start at the Galena & US Grant Museum, located in an 1858 mansion, to learn the history of the town, former home to 18th US President Ulysses S. Grant. Grant’s home, with its original furnishings, is also open to tour. Head from there to Dowling House, Galena’s oldest home, built in 1826. The Haunted Galena Tour Company recently added a Spirits & Spirits Tour, a 90-minute, three-drink ghost tour which takes you through a haunted brewery, restaurant and hotel. Other new attractions include Galena Jeep Rentals and, in nearby Stockton, the just-opened Valley of Eden Bird Sanctuary, which spans 409 acres with more than six miles of trails. Also nearby, pick apples from more than 5,500 dwarf trees at Terrapin Orchards, which opens for the season on Sept. 8.

Where to stay: The DeSoto House Hotel is Illinois’ oldest operating hotel, with 55 Victorian-style guest rooms. At Aldrich Guest House, a popular bed and breakfast, innkeepers Robert and Douglas Mahan make next-level breakfast dishes, in addition to hors d’oeuvres for a daily wine hour. If you’re looking to go all out, Eagle Ridge Resort & Spa offers free-standing villas that offer privacy with access to all of the resort activities, including boating, fishing, ziplining, horseback riding and hot air ballooning.

What to eat and drink: Pudgy’s just opened on Main Street with Chicago-style hotdogs and loaded cheese fries, while Galena classics include the steakhouse Log Cabin and Italian restaurant Vinny Vannuchi’s, both also on Main Street. Drive 20 minutes to the shores of the Mississippi River to find new Millennium Bar & Marina in East Dubuque, offering waterfront seafood boils, burgers and dangerous-looking rum buckets.

Featured image by Todd Ryburn Photography/Getty.

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