Every year around this time, the appeal of the great getaway beckons for overworked urbanites who need to escape it all. Yet the logistics of air travel—getting to O’Hare, TSA lines that take 25 minutes to negotiate, sardine-tin seating situations—will dampen even the most enthusiastic wanderlust. If this sounds familiar, you may be interested to know that within a manageable drive from Chicago’s celebrated skyline lie hidden sanctuaries of culture, cuisine, contemplation, and indulgence. This is Seeking, after all, and our members expect nothing less. And just to clarify, these aren’t your granny’s road trips, replete with kitschy diners and dubious roadside motels: we are talking curated luxury experiences for those dating in Chicago.
Small Town Charm
Galena is the undisputed jewel of northwest Illinois. A three-hour drive through rolling farmland transports you to a village that time seemingly forgot. Once home to Ulysses S. Grant, Galena and its Main Street offers a picturesque and intact tableau of 19th-century architecture. But don’t be fooled by the quaint facades. Galena pulses with a quiet sophistication that belies its small-town roots. For lodging, eschew the predictable chain hotels that hog the outskirts of the town. Instead, head to Jail Hill Inn, award-winning boutique lodgings housed in a meticulously restored 1878 county jail where exposed brick walls and luxurious linens coexist perfectly. Five of the six suites occupy over 800 square feet of opulence, ensuring ample space for romance and reflection.
Culinary adventurers will find much to get excited over at Fritz and Frites, an unexpected but highly successful fusion of German and French cuisines in an intimate bistro setting. The schnitzel—crisp and golden, of course—shares menu space with a delicate coq au vin. It’s a culinary Franco-Prussian détente that would have seen even Bismarck and Napoleon raise a glass in observation of what this small but chic eatery achieves.
Blaum Bros. Distilling Co. offers a masterclass in artisanal spirits for those desiring liquid inspiration. Their Hellfyre Vodka, made by soaking plenty of fresh, hand-cut jalapeños, habaneros, and black peppercorns in vodka, is not for the faint of heart—or palate, for that matter. It’s an appropriate metaphor for Galena itself: unassuming at first acquaintance but capable of making a deep and lasting impression.
Dancing By The Lake
Nestled in the heart of Wisconsin’s lake country, Lake Geneva is a picture-perfect resort town, once the playground of Chicago’s Gilded Age elite, now offering a sophisticated blend of natural beauty and refined indulgence that will elevate any budding romance. The Grand Geneva Resort and Spa is a sprawling 1,300-acre property that started out as the infamous Lake Geneva Playboy Club Hotel in the late 60s. Here, indulgence is not a concept but a tangible experience. The resort’s WELL Spa + Salon provides an array of treatments that will leave you refreshed and radiant for the evening ahead. For the adventurous, the resort’s ski hill offers a thrilling backdrop for a seasonal winter adventure.
For a touch of whimsy, venture to the Maxwell Mansion Speakeasy, a hidden gem that requires a daily changing password—found on their Facebook page—to enter. Once inside, you’re transported to a world of craft cocktails and clandestine charm, setting the stage for intimate conversation and shared secrets.
In Lake Geneva, luxury isn’t about ostentation but the subtle elegance of shared experiences. It’s in the way the light glistens on the lake at dusk, the rich history that seems to pour from every corner, and the promise of memories yet to be made. While summer on the lake is justifiably revered with the rich and famous and their Italian speedboats, winter is, in a word, magical.
Between Two Lakes
But perhaps it’s a more cerebral escape that is called for, and in that case, set your sights on Madison, Wisconsin. This isthmus city, nestled between lakes Mendota and Monona, offers a full-bodied blend of Midwestern charm and cosmopolitan flair. For lodging, it’s best to bypass the predictable downtown options and instead seek out The Livingston Inn, a meticulously restored 1854 Gothic revival mansion and make sure to request the William T. Leitch room, Named in honor of the builder of this glorious mansion, where original pine floors and a marble fireplace set the stage for literary-inspired reveries and a perfect romantic weekend.
And when it comes to nourishing both body and mind, Eno Vino Downtown is just the palace. Located on top of the AC Hotel, the wine bar and bistro offers panoramic views of the impressive state capitol building while a small-plate menu encourages non-stop sharing and conversation. Then, as night falls, it’s a great time to your way to the Memorial Union Terrace. Here, overlooking Lake Mendota, colorful chairs dot the shoreline since it’s a popular gathering place for students, professors, and locals alike with a robust seasonal events roster, so do look to see what you may see when you visit. Order a scoop of Babcock Ice Cream—the result of UW-Madison’s own dairy program—and engage in that most collegiate of pastimes: a spirited debate on the nature of existence, fueled by sugar and lactose and the crispness of Midwest nights.
Go North
Ensconced between Lake Michigan and Green Bay, Door County, with its Scandinavian heritage and rustic charm, has quietly cultivated an allure that beckons those in search of both natural splendor and cultural richness. Edgewater Resort in Ephraim, where lakefront suites offer panoramic views of Eagle Harbor, is perfection. Indulgence is about thread count, yes, but it’s also about a sense of serenity that envelopes you each morning. The resort’s dedication to personalized service ensures that your every whim is anticipated and met with understated elegance.
The Door County peninsula is practically an open-air museum, given its 80 galleries dotting the landscape. For an immersive experience, visit the Peninsula School of Art in Fish Creek, where you may observe master artists at work or even partake in a workshop, honing your own creative skills under expert tutelage.
And don’t fear; culinary adventurers will equally find Door County an unforgettable playground. Secure a reservation at Thyme in Sister Bay, a farm-to-table celebration of life and food with a daily-changing menu offering a culinary journey through the region’s terroir.
Midwest Charm Meets Coastal Sophistication
Often referred to as the “Art Coast of Michigan,” Saugatuck offers a refined blend of natural beauty, culinary excellence, and cultural sophistication that belies its unassuming Midwestern roots. The Hotel Saugatuck is a restored 1865 landmark and now the town’s premier boutique bed and breakfast. Here, luxury is a tangible experience, and gourmet breakfasts are served with impeccable attention to detail, setting the tone for days filled with curated experiences.
For those aspiring to a somewhat more aquatic adventure coupled with a touch of nostalgia, Retro Boat Rentals offers a fleet of restored vintage vessels. Glide across the waters of the Kalamazoo River in a 1950s Chris-Craft or a classic Century, the gleaming mahogany and chrome starkly contrasting the ultra-lush shoreline.
The Saugatuck Center for the Arts serves as the area’s cultural epicenter, offering a rotating array of exhibitions showcasing local talent and internationally renowned artists. For those wanting a more intimate artistic encounter, the J. Petter Galleries presents an opportunity to acquire museum-quality pieces, perhaps a lasting memento of your Saugatuck stay.
No luxury weekend is complete without at least some culinary indulgence, and Saugatuck delivers with understated elegance. Pennyroyal Cafe & Provisions stands out as a beacon of farm-forward cuisine, where each dish is a testament to the region’s agricultural bounty. For an evening of refined dining, Bowdie’s Chophouse presents an sophisticated menu that rivals any metropolitan steakhouse, with prime cuts that demand advance reservations.
Midwest luxury lies in how the morning light filters over the lake, through orchards, and past barns. It appears when you uncover perfectly balanced—locally sourced—flavors at fall harvest tables served next to a stream; and it’s there when you sip cocktails on the beach watching a perfect lakeside sunset. For those wanting a weekend that matches natural beauty with cultural richness and a relaxed pace, the places in Chicago’s backyard stand as hidden jewels—destinations that reward the curious and leave the initiated with a deep longing to return.
At Seeking, we think that building a life, much like a romantic weekend getaway, is about shared purpose. And a sense of journey. We appreciate that meaning is often found in the details, and that connection is not solely based on physical attraction but also on shared goals, intellectual curiosity, and a desire for a fulfilling partnership. We invite you to join Seeking today!
