8 Weekend Getaways from Chicago for a Quintessential Midwestern Vacation

Located northeast of Green Bay perched along a scenic peninsula, Wisconsin’s Door County region is dotted with charming small towns, waterfront parks, and public beaches that have helped earn this Midwest vacation paradise the nickname of the “Cape Cod of the Midwest.”

Each town provides its own character, from the lively tourist centers of Fish Creek and Egg Harbor to the more hidden out-of-the-way locales like Bailey’s Harbor and Gills Rock (the latter from which you can board a ferry to the old fisherman village of Washington Island or journey on to the remote Rock Island State Park).

A great base of operations for exploring the Door County area is the affable town of Sister Bay, where the friendly couple who run the Open Hearth Lodge is more than willing to point you in the right direction. You’ll feel right at home in the basic yet supremely comfortable rooms or suites of the recently expanded property, where an expansive backyard offers short hiking trails and a patio deck perfect for popping open a bottle of locally-produced wine while relaxing in the sun. And fiery sunsets over the water don’t get much better than those enjoyed at Fred & Fuzzy’s Waterfront Bar & Grill, located within walking distance of the lodge with live music most nights in the summer.

Nestled along the Mississippi River near Illinois’s western border with Iowa, the rolling hills and peaceful farmland surrounding the historic town of Galena provides the perfect opportunity to step back in time. Stroll the charming cobblestone streets of its amazingly well-preserved downtown to admire the historic mansions along Main Street while picturing what life was like during the days of Ulysses S. Grant, one of several Civil War generals to once call this placid riverside community home.

Romantic Italian architecture and European-style accommodations greet weary city travelers at Cloran Mansion Bed & Breakfast, located on the outskirts of town with plush gardens providing aristocratic opportunities for overlooking the gorgeous two-storey brick mansion structure. Inside your room, relaxation options include either cuddling close amidst the wood cathedral ceiling and the stained glass window of the quaint Ann’s Room or spreading out in the pet-friendly, 570-square-foot Antonio’s Cottage centered around a two-person Jacuzzi with clear three-sided fireplace.

Country breakfast comes in six delicious courses around here but don’t worry, there’s plenty of time for digestion kicked back in sturdy wood Adirondack chairs overlooking the mansion’s outdoor patio fire pit.

In the words of a certain Zoolander character, Grand Rapids is “so hot right now.” One of America’s fastest-growing cities is a modern-day boomtown built on the back of craft beer, urban art, and fresh farm-to-table cuisine that has turned Michigan’s second-largest city into a bona fide tourism juggernaut. The once-sleepy city is known for hosting one of the highest number of breweries per capita of any city in the United States, but its highly walkable downtown also offers quintessential urban experiences with expansive parks and modern architecture dotting the shores of the Grand River.

Thankfully with so much beer involved, you’re able to leave the car at the hotel when basing your operations around the centrally located JW Marriott Grand Rapids, situated alongside the shores of the Grand River just outside the scenic River Edge Trail. Inside the hotel, you’ll find spacious, modern rooms and suites (many of which overlook the river) with spa, beer, and romance packages also available to customize your stay. Dig into steak tartare and coq au vin at the on-site French bistro Six.One.Six before clinking glasses in the hotel’s Mixology bar over cocktails and happy hour punch.

This being Grand Rapids, you can also try local Michigan beers from the likes of Founders, Bell’s, and Brewery Vivant, all without leaving the comfort of your hotel. But if you want to grab a “Beer City Brewsader” passport and explore some of the city’s 40-plus breweries and brewpubs, that’s quite alright as well. You’re also within easy walking distance from the hotel of several galleries and museums, including the Grand Rapids Public Museum and Grand Rapids Art Museum.

The clean and compact city of Indianapolis is often overlooked by Midwest travelers, but those quick to discuss Indiana’s capital city are missing out on its myriad understated charms. The downtown district is blessed with a wide array of highly walkable attractions. There’s iconic Soldiers & Sailors Monument (the city is home to the most war memorials outside of Washington D.C.), the Indiana State Museum, the lesser-known Kurt Vonnegut Museum & Library (the famed author is from here), and the criminally underrated Indianapolis Zoo located on the leafy riverside grounds of downtown’s picturesque White River State Park.

An ideal spot from which to explore Indy’s wealth of downtown attractions is the arts-centric Conrad Indianapolis, which features a unique package of suites in “The Collection” which are each devoted to a certain art genre and include signed pieces by noted artists such as Pablo Picasso, Andy Warhol, and Salvador Dali. Even if you’re not staying in such artsy rooms as the vibrant “Modernism” or “Surrealism” suites, standard accommodations here are bright and airy with a nice view overlooking downtown. When you get hungry, carve up some expertly cooked chops at the Conrad’s old-school Capital Grille or sample a massive assortment of wines from Tastings, one of the world’s largest by-the-glass tasting rooms.

Also, be sure to stop by the hotel’s Evan Todd Spa & Salon to get you looking prim and proper for a night on the town. And if it’s snowing outside, not to worry. An elevated skywalk connects the property to downtown’s Circle Center Mall and Indiana Convention Center.

The Midwest is famous for its many storied Big 10 university campuses, and the fun and friendly college town of Iowa City earns its place on any college football fan’s itinerary. Iowa City is also one of the most educated and literary cities in the country, designated as the world’s third “City of Literature” by UNESCO while showcasing the Iowa Avenue Literary Walk—a tamer Hollywood Walk of Fame-style installation featuring bronze plaques carved into the sidewalk displaying quotes from famous authors tied to the city.

If you want to be in the midst of the action, it’s hard to be more centrally located than the Hotel Vetro. Its 56 modern-styled suites give off a homey vibe as you settle in for a quiet night of reading in plush superior beds or get ready for a raucous night on the town overlooking the action with a drink in hand from your balcony in the corner Zelen Suite.

If you’re hungry, make your way down to the ground level for wine and sushi at Formosa before heading out into town to mingle (and maybe discuss your latest read) with a laid-back yet friendly crowd of locals and college students at local hangouts like George’s Buffet. Be sure to grab a burger while you’re here—easily one of the best in the state.

You’re getting a water-inspired spa treatment at one of the world’s top-rated spas. You’re golfing on one of four championship courses, all of which are rated on Golf Digest’s list of 100 Best Courses. And dinner just so happens to be at the number one rated hotel restaurant in the world, according to USA Today’s 10Best readers.

This is not a dream. This is a weekend at The American Club in Kohler, Wisconsin, one of the most luxurious getaways in the Midwest if not the country. Located just west of the lakeside town of Sheboygan next to a 500-acre private wilderness preserve, the 241 rooms of this ultra-luxurious five-star resort feature insanely plush bedding amidst dark woods and jewel-toned fabrics that will make you feel like the president (even if you’re not staying in the hotel’s posh Presidential Suite).

If that’s not enough, there’s yoga overlooking the lake and a range of entertainment options including culinary theatre and an arts and design center. With so much to see and do on the resort campus, it wouldn’t come as much of a surprise to anyone if you took Monday off to stay another day.

Located just 90 minutes north of Chicago but seemingly in another world, Lake Geneva is the stuff of lakeside summer vacation dreams. The popular year-round destination has been a haven for Chicagoans on holiday for generations, but now welcomes a diverse crowd of travelers from all walks of life. Nature seekers can rent a boat on the lake or walk the spectacular Lake Geneva Shore Path winding 26 miles along the shore, while those looking for action can find plenty of entertainment shopping or bar-hopping along the Main Street Historic District.

Tucked away from the bustling town of Lake Geneva on the quieter side of the lake in the small community of Fontana, The Abbey Resort has everything you need from well-appointed guest rooms overlooking the lake to vacation villas for the whole family. Feel the stress of urban life melt away at the resort’s on-site Avani Spa, take in breezy outdoor film screenings on their large grassy grounds, or knock back drinks as you watch the flames of the fire flicker outside their Waterfront restaurant (which hosts live bands most summer weekends.)

The full-service resort also features a game room and pools or, if you’re in the mood for the real thing, you’re just a short walk to a small sandy beach near iconic local watering hole Chuck’s Lakeshore Inn.

Milwaukee is often misunderstood as an unsophisticated throwback town consisting of beer, cheese, and little else. But with a booming food scene, underrated art galleries, and one of the most overlooked public park systems in the U.S., those misconceptions will immediately melt away after you spend a weekend in Milwaukee biking the Oak Leaf Trail or exploring the funky shops of the Historic Third Ward. The tailgate scene at Milwaukee Brewers ballpark Miller Park is also legendary, so be prepared to make some new friends.

Opened in 2008 in a renovated 100-year-old warehouse building, the hip Iron Horse Hotel is a central meeting place for Milwaukee’s “in” crowd thanks to 100 loft-style rooms that will make you feel like a local with exposed brick walls, hardwood floors, and antique lounge sofas. The motorcycle-friendly property (located just across the river from the city’s popular Harley-Davidson Museum) also features an on-site bike washing station as well as two of the hippest bars in the neighborhood: the sleek mixology bar Branded and outdoor hotspot The Yard.

Dinner is served at the hotel’s blacksmith-inspired restaurant Smyth and, if you so choose, you can also spend the day with Smyth’s chefs watching them prepare a special dinner for two as part of the hotel’s Farmer’s Market Dinner package. What could be cooler than that?