Picture this: Sinking into a plush spa robe, a glass of bubbly in hand, with breathtaking scenery as your backdrop. No, you’re not dreaming! If you’re looking for a way to relax and recharge over the weekend, there are plenty of luxury getaways near Chicago that promise to rejuvenate your senses and elevate your spirit.
The best part? To distinguish themselves, some of these getaways invest in staff with a Masters in Luxury Management. In other words, you’re guaranteed a level of personalized attention and expertise that surpasses all expectations.
Chicago’s relentless energy can be replaced with pure relaxation in a matter of a few hours. These luxurious escapes are calling your name. Are you ready to answer?
1. Lake Views: Lake Geneva, WI
- Distance from Chicago: 80 miles
- Drive time: 1 hour and 15 minutes
Staying at Lake Geneva means immersing yourself in an atmosphere of opulence and serenity. The town’s upscale resorts and boutique hotels offer a wide range of amenities designed to pamper and please. From spa services that draw inspiration from the natural beauty surrounding the lake to gourmet dining experiences that feature locally sourced ingredients, every aspect of your stay is crafted to delight the senses.
Adventure seekers will find plenty to satisfy their thirst for excitement, with activities that make the most of the area’s stunning natural landscape. Book a private boat to experience the tranquility of the lake from the water or challenge yourself on one of the championship golf courses that offer not only a game but a vista.
For those who prefer things to be more laid-back, Lake Geneva makes an ideal weekend getaway from Chicago. A stroll along the lake’s edge or a few hours on the beach can be the perfect way to unwind.
The shopping and dining options complement the entire upscale experience, with boutique shops offering unique finds and restaurants catering to discerning palates. There are also some creative local eateries to check out, like the locally owned Scoops ice cream shop (a personal favorite indulgence).
ⓘ PRO TIP: Speaking of ice cream, Meggy Moo’s Dairy Ripple is worth the short drive to Walworth. This iconic 1950s drive-up ice cream joint has managed to keep its charming, retro charm, and the ice cream still tastes just like it did when I was a kid.
- Recommended Stay: The French Country Inn
2. Golf & Wellness: Kohler, WI
- Distance from Chicago: 144 miles
- Drive time: 2 hours and 15 minutes
If unwinding at a world-class spa is your definition of a luxurious retreat, then Kohler, Wisconsin, has the perfect destination for you. Located in this peaceful town, the Kohler Waters Spa at The American Club is the ultimate haven of relaxation and rejuvenation. It’s been recognized as one of the most innovative and comprehensive spa experiences in the Midwest.
The spa’s signature treatments, inspired by water’s restorative power, are designed to soothe, rejuvenate, and invigorate the body and mind. From hydrotherapy services that harness the therapeutic benefits of mineral-rich water to personalized massages that address your individual needs, each treatment is a testament to the spa’s commitment to excellence and innovation.
Beyond the spa, the resort is a golfer’s paradise, boasting four championship courses designed to challenge and delight players of all levels.
- The Straits Course, designed by Pete Dye.
- The Irish Course, designed by course architect Robert Trent Jones Jr.
- The River Course, designed by renowned golf course architect Dick Nugent.
- The Meadow Valleys Course, also designed by Dick Nugent.
These meticulously maintained courses, set against the backdrop of Kohler’s stunning natural beauty, offer a golfing experience that is both challenging and visually captivating.
- Recommended Stay: The American Club
3. Romantic Retreat: Galena, IL
- Distance from Chicago: 144 miles
- Drive time: 2 hours and 45 minutes
For couples seeking a romantic escape, Galena offers an intimate setting characterized by its beautifully restored historic homes, which have been transformed into luxurious bed and breakfasts, providing the perfect backdrop for a love-filled getaway.
The town’s quaint shops and art galleries offer treasures waiting to be discovered, perfect for a leisurely day spent hand in hand. For those who appreciate the finer things in life, Galena’s local vineyards provide intimate wine tastings, offering a taste of the region’s rich viticultural heritage. These experiences, often set against the backdrop of picturesque vineyards, promise not only a sensory delight but also moments of connection and romance.
As the day fades into the evening, Galena’s culinary scene comes alive, offering romantic dining options that cater to every taste. From intimate candlelit meals in historic buildings to casual eateries with charming outdoor patios, couples can end their day with a meal that feels tailor-made for them.
- Recommended Stay: The Steamboat House
4. Outdoor Adventure: Starved Rock State Park, IL
- Distance from Chicago: 203 miles
- Drive time: 3 hours
Located less than two hours from Chicago, this natural sanctuary is the ideal destination for adventurers who don’t want to compromise on comfort. With a choice of luxurious cabins as well as an historic lodge tucked among the park’s towering trees, these buildings offer a unique mix of rustic charm and modern luxury, so guests can enjoy the outdoors without giving up the comforts they love.
Outdoor enthusiasts will find no shortage of activities to fill their days at Starved Rock. Beyond hiking, the park offers opportunities for fishing, boating, and bird watching, with the Illinois River providing a backdrop for adventure and exploration. In the colder months, the park transforms into a winter wonderland, with ice climbing, cross-country skiing, and eagle watching becoming favorite pastimes.
Returning to a luxurious cabin after a day of exploration elevates the experience from a simple outdoor adventure to a truly indulgent escape. These cabins are designed with both comfort and style in mind, featuring cozy fireplaces, plush bedding, and often, private hot tubs under the stars. It’s a place where guests can unwind and recount the day’s adventures, enveloped in warmth and luxury.
- Recommended Stay: Starved Rock Lodge & Conference Center
5. Beachside Bliss: Harbor Country, MI
- Distance from Chicago: 75 miles
- Drive time: 1 hour and 15 minutes
Just a stone’s throw from Chicago’s bustling heart, Harbor Country unravels along the Michigan shoreline. This tapestry of eight charming towns whispers promises of a sophisticated and serene escape. Miles of pristine beaches appear, inviting you to lose yourself in some of Lake Michigan’s prettiest coastal landscapes.
Not all beaches are created equal, though. Lake Michigan’s shoreline offers a quirky coolness factor: the Singing Sands. These rare shores transform your walk into a symphony. As your feet dig into the sand, you’ll hear a melodic hum or squeak, unlike anything you’ll experience anywhere else.
Harbor Country is a shopper’s dream, offering everything from an outlet mall to upscale boutiques selling artisan crafts and high-end fashion. Instead of those generic “big box” stores, you’ll find a wide selection of shops that reflect the unique character and charm of these lakeside communities.
Gourmet dining is another highlight. The area’s restaurants range from casual eateries serving up local favorites to fine dining establishments offering innovative dishes prepared by acclaimed chefs. Many of these dining spots pride themselves on farm-to-table offerings, showcasing the best of what the local farms and vineyards have to offer.
ⓘ PRO TIP: If you’re coming from Chicago, the first public beach in Michigan is New Buffalo City Beach, just 10 miles past Michigan City Beach in Indiana.
- Recommended Stay: Goldberry Woods
6. Wines & Vines: Three Oaks, MI
- Distance from Chicago: 75 miles
- Drive time: 1 hour and 15 minutes
Wine lovers yearning for a luxurious getaway from Chicago should head to Three Oaks, Michigan. This charming Harbor Country town sits right in the heart of the Lake Michigan Shore Wine Trail. The Trail is a collection of wineries that are committed to making exceptional wines from grapes grown in the Lake Michigan Shore AVA (American Viticulture Area).
With a collection of over 20 wineries to enjoy, you’ll be able to spend your days indulging in tastings from a diverse range of vineyards, all within a short drive.
Three Oaks itself offers a touch of sophistication with a small-town feel. You’ll find high-end art galleries, unique shops, and acclaimed restaurants alongside the wineries, making it a great place to base yourself for exploring the area. Many of the wineries even have beautiful views of vineyards or lakes, adding to the luxurious feel of your getaway.
- Recommended Stay: Three Oaks Inn B&B
7. Art Lover’s Paradise: Saugatuck, MI
- Distance from Chicago: 141 miles
- Drive time: 2 hours and 10 minutes
Saugatuck is a gem on the shores of Lake Michigan, known for its vibrant arts scene and stunning natural beauty. This picturesque town, often referred to as the “Art Coast of Michigan,” offers an idyllic setting for an artistic retreat that combines luxury with creativity. Saugatuck is home to numerous art galleries, studios, and boutiques.
Accommodations in Saugatuck cater to the discerning traveler who appreciates the finer things in life. Wake up to gourmet breakfasts in a beautifully restored historic home, spend your day exploring the artistic treasures of the town, and unwind in the evening with a glass of wine on a secluded porch overlooking the water.
Luxury boat tours offer a unique way to experience the lake, some coming complete with catered meals and private viewings of the sunset. For those looking to immerse themselves in creativity, workshops and classes are available, ranging from painting and pottery to photography, offering a hands-on way to engage with the art world.
- Recommended Stay: Twin Oaks Inn
BONUS: Historic Escape: French Lick Resort, IN
- Distance from Chicago: 289 miles
- Drive time: 4 hours and 45 minutes
Clocking in at nearly a 5-hour drive, French Lick Resort wasn’t a contender on my list of luxury getaways near Chicago. However, this Indiana destination shouldn’t be overlooked.
This meticulously restored haven, restored to its early 20th-century glory, whisks you back in time. Imagine yourself enveloped in lovingly preserved details, a privileged guest experiencing a bygone era firsthand.
But the elegance doesn’t end there. This exclusive accommodation seamlessly integrates modern luxuries, guaranteeing an escape that’s as comfortable as it is captivating.
The resort’s world-class spas are sanctuaries of relaxation and rejuvenation, seamlessly integrating the healing benefits of local mineral springs into their treatments. Book the exclusive Historic Signature Sprudel Bath and let West Baden Springs’ mineral-rich thermal waters alleviate stress and pain while nourishing the skin.
Golf enthusiasts will find themselves in a golfer’s paradise, with the resort boasting several championship golf courses. These courses are designed not only to challenge but also to captivate, with breathtaking views and lush landscapes that make every round an unforgettable experience.
- Recommended Stay: French Lick Resort
Getaways Near Chicago: My Final Thoughts
Whether it’s for a week or a weekend, getaways provide more than just a break from the daily grind. They offer an experience that touches the soul and redefines the essence of indulgence.
I hope these destinations fulfill your deepest desires for indulgence, comfort, and rejuvenation. You deserve to escape the ordinary and embark on a journey where luxury knows no bounds.
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