Looking for quick getaways from Chicago? Southwest Michigan offers the perfect escape year-round, boasting rich fall colors, cozy winter landscapes, and summer lake activities. The region’s small-town charm and unique attractions make it a hidden gem of the Midwest.
Quick Guide to Planning a Trip to Southwest Michigan
Whether you're a wine lover or an antique enthusiast, we're rounding up the top reasons to visit Southwest Michigan and the most beautiful Lake Michigan vacation rentals.
When you think of wine-growing regions, Michigan likely isn't the first place that comes to mind. However, the state's unique geography makes it the perfect location to grow a variety of grapes, including Niagara and Concord. Since Southwest Michigan is on the southern end of Lake Michigan, the area experiences something known as the lake effect, causing moderate temperatures that don't hit extreme lows or highs. This temperate climate creates the perfect grape-growing conditions.
Michigan is quickly gaining recognition for its world-class wines and we highly recommend exploring the Lake Michigan Shore Wine Trail on your visit. The Wine Trail features a collection of twenty-one wineries and vineyards spanning Southwest Michigan. Outlined below are two of our favorite local wineries.
Address: 185 Mt. Tabor Rd, Buchanan, MI 49107
Location: Buchanan | Distance From Chicago: 1 hr 34 min
Sip and stroll at Tabor Hill Winery & Restaurant, where you can explore the Mt. Tabor Trails, 3.6 miles of vineyard and woodland paths connecting the winery to its sister property, Round Barn Estate, while enjoying a glass of wine along the way. If you'd rather sit back and relax, the winery pairs award-winning Riesling, Chardonnay, and Pinot Noir with a farm-to-table restaurant overlooking the vines. Stop by on a summer weekend for live acoustic music on the patio.
Address: 533 E Lemon Creek Rd, Berrien Springs, MI 49103
Location: Berrien Springs | Distance From Chicago: 1 hr 37 min
Experience a farming legacy that spans more than 165 years at Lemon Creek Winery. Lemon Creek offers a diverse portfolio of estate-grown wines, from dry reds and whites to sparkling wines, rosés, and dessert vintages, all poured in a tasting room surrounded by 170 acres of vineyards. If you're bringing along kiddos, we recommend visiting during U-pick season, when you can harvest your own fruit. Families enjoy picking cherries and peaches in the summer and apples and grapes in the fall.
Address: 111 W Shawnee Rd, Baroda, MI 49101
Location: Baroda | Distance From Chicago: About 1 hr 40 min
Dablon Vineyards & Winery is a family-owned estate perched on one of the highest points in Baroda, where terraced vineyard blocks with stone-lined walls follow the rolling hills. The winery grows close to 20 varietals and crafts more than 30 wines, including grapes rarely seen in the Midwest like Malbec, Tannat, and Petit Verdot. Settle in at the granite tasting bar, watch the winemakers at work through the production windows, or take your glass out to the terrace overlooking the vines. The tasting room is open 363 days a year, and winter visitors can even go snowshoeing through the estate.
Address: 750 Browntown Rd, Buchanan, MI 49107
Location: Buchanan | Distance From Chicago: About 1 hr 35 min
For a smaller, more personal stop on the wine trail, visit Hickory Creek Winery, a veteran-owned producer of old-world European-style wines made entirely from Lake Michigan Shore grapes. Tastings happen inside a charming red barn or out on the patio, where guided flights of five wines run $15 per person. Look for standouts like Riesling, Pinot Gris, Cabernet Franc, and the local favorite, Heirloom Apple. The winery is family- and dog-friendly, so everyone in your crew is welcome.
Address: 6130 122nd Ave, Fennville, MI 49408
Website: Fenn Valley Vineyards (IG)
Location: Fennville | Distance From Chicago: About 2 hr 15 min
Family owned and operated since 1973, Fenn Valley Vineyards produces wines and hard ciders from fruit grown along the Lake Michigan shore, and its bottles have earned more than 200 awards. You can book an extended tour led by a member of the Fenn Valley team to see the whole vine-to-glass process or simply settle in for a tasting in the year-round tasting room. Time your visit around one of their summer evening cook-outs or the annual wine festival held in the middle of the 240-acre property.
Address: 11945 Red Arrow Hwy, Sawyer, MI 49125
Location: Sawyer | Distance From Chicago: About 1 hr 20 min
Solasta Winery is one of the newest additions to the Sawyer wine scene, sitting directly across from Warren Dunes State Park. This small-batch winery pours 19 wines, from bold reds and crisp whites to bubbly rosé and wine-based cocktails, alongside curated charcuterie boards and a s'mores board the kids can roast by the fire pits. The covered, heated patio keeps the outdoor seating comfortable year-round, and live music plays every Sunday afternoon. Kids and friendly dogs are always welcome.
Thanks to a combination of local talent and skilled Chicago expats, the Southwest Michigan food scene is booming with incredible eats. Since the area offers an abundance of fresh produce and farm-raised meats, many restaurants cook with local ingredients sourced from the farms and fields around them. We think you'll enjoy the following local favorites.
Address: 111 W Water St, New Buffalo, MI 49117
Location: New Buffalo | Distance From Chicago: 1 hr 26 min
Terrace Room offers an authentic taste of Italy right on the shores of Lake Michigan. This waterfront restaurant inside the Harbor Grand Hotel is known for its rustic Italian fare, including handmade tagliatelle and pappardelle bolognese built from simple, fresh, seasonal ingredients. Enjoy your meal on the harborside terrace in the warmer months. As the weather cools, cozy fireside dining inside provides a romantic setting to savor a comforting meal while still enjoying the scenic lake views.
Address: 5851 Sawyer Rd, Sawyer, MI 49125
Location: Sawyer | Distance From Chicago: 1 hr 15 min
Located in the historic Flynn Theater building in downtown Sawyer, Susan's combines Chicago city vibes with the charm of Southwest Michigan. The cozy ambiance invites you to enjoy an elevated yet approachable menu. Each dish is crafted with the finest local and imported ingredients, reflecting both the seasons and Chef Mike Kinasz's creative inspirations. In warm weather, grab a table on the large pet-friendly patio, and don't leave without spotting Susan herself in the painting that overlooks the bar.
Address: 11 W Merchant St, New Buffalo, MI 49117
Location: New Buffalo | Distance From Chicago: About 1 hr 15 min
In the heart of downtown New Buffalo, Brewster's New Buffalo is a locally owned restaurant with deep Italian roots that serves breakfast, lunch, and dinner seven days a week. The kitchen turns out wood-fired sourdough crust pizzas, fresh handmade pasta like cacio e pepe, housemade sauces, and creative globally inspired specials that change with the seasons. Pair your meal with a signature cocktail, then linger over dessert on the patio or in the sunny atrium.
Address: 800 Whitwam Dr, St. Joseph, MI 49085
Location: St. Joseph | Distance From Chicago: About 1 hr 45 min
Set inside The Inn at Harbor Shores on one of the oldest harbors in the Great Lakes, Plank's Tavern on the Water celebrates American food and drink with a menu built on the region's agricultural bounty. Grab a seat at the dockside bar for craft beer, craft cocktails, and live music, or settle onto the heated waterfront patio and watch the boats come and go. If you fish, the restaurant even participates in Michigan's Catch and Cook program, so the chef can prepare your fresh catch right off the dock.
Skip the touristy souvenir shops and bring back something truly unique by exploring local antique stores. Mixing modern and antique items is a design tactic used by some of the world’s top interior designers. Not only does it provide visual interest in your home, but it also allows you to showcase treasures from your favorite trips. We think you’ll love the following Michigan antique stores.
Address: 19 S Elm St, Three Oaks, MI 49128
Location: Three Oaks | Distance From Chicago: 1 hr 22 min
Trilogy Antiques & Design features a select group of art and antique dealers who share distinctively great taste. Vintage furniture, textiles, lighting, and art draw designers from all over the country hunting for one-of-a-kind pieces. This curated experience feels more like stepping into a beautiful art gallery than a traditional antique store, and owner Brandon Nelson's playlist is always a bonus.
Address: Lake Bluff Park, 400 Lake Blvd, St. Joseph, MI 49085
Location: St. Joseph| Distance From Chicago: 1 hr 39 min
Antiques on the Bluff is a premier antique show held along Lake Bluff Park in St. Joseph, with Lake Michigan as the backdrop. It features more than 50 vendors and runs on the first Sunday of each month from May through October, rain or shine, from 10 a.m. to 5 p.m. Browse vintage furniture, collectibles, and rare finds, then walk downtown St. Joseph's shops and beaches to round out the day.
Address: 2948 Blue Star Hwy, Douglas, MI 49406
Location: Douglas | Distance From Chicago: About 2 hr 15 min
If you want a full afternoon of treasure hunting, head north to Saugatuck Antique Pavilion, widely considered one of the best antique shopping experiences in the country. More than 24,000 square feet of high-ceilinged, wide-aisled space holds booths from 175 dealers selling everything from Herman Miller furniture and Depression glass to vintage vinyl and Civil War era collectibles. The pavilion connects directly to Saugatuck Brewing Company, and your same-day receipt earns you 10 percent off your food there. Open daily from 10 a.m. to 6 p.m.
Address: 638 E Shawnee Rd, Baroda, MI 49101
Location: Baroda | Distance From Chicago: About 1 hr 40 min
Operating since 1969, Shawnee Road Antiques is Southwest Michigan's oldest and largest private antique shop, spread across three barn buildings just outside Baroda. You'll find roughly 300 pieces of furniture plus thousands of smaller items, from formal Art Nouveau and Art Deco pieces to country primitives, crocks, and architectural salvage. Don't miss Apparel from the Past inside the blue barn, home to the region's largest collection of women's vintage clothing dating from the late 1800s to the 1970s. Bring cash or a checkbook, since cards aren't accepted.
Looking for a beach vacation without the blistering heat? Southwest Michigan is home to one of the largest freshwater seas in the world, Lake Michigan. Summer temperatures rarely exceed 80°F, making it an ideal spot for a classic beach vacation without the intense heat typically associated with summer trips. If you're planning a Michigan getaway, you likely have a few beaches on your list already. To fully enjoy the lake, consider booking one of these memorable water-based activities.
Address: 9 W Mechanic St #A, New Buffalo, MI 49117
Location: New Buffalo
Distance From Chicago: 1 hr 18 min
Set sail on Lake Michigan with New Buffalo Sailing Excursions. Experience personalized charters aboard a 31-foot sailboat for groups of up to six, from family day sails and swimming stops to romantic sunset cruises, and you can take the helm or simply relax on deck. While New Buffalo Sailing Excursions doesn't serve alcohol, guests are welcome to bring their own beverages. We suggest grabbing a bottle of local wine to enjoy during your two-hour sail. The charter season runs mid-May through mid-September.
Address: On the St. Joseph River, St. Joseph, MI
Location: St. Joseph
Distance From Chicago: 1 hr 45 min
Interested in creating an experience the entire family will enjoy? Check out Lake Life Watersports. This company offers wave runner and pontoon rentals by the hour, providing everything you need for a fun-filled day on the water. Cruise the scenic St. Joseph River, head out along the Lake Michigan shoreline, or anchor off Silver Beach for a swim. Full and half-day fishing trips are also available if you'd rather cast a line.
Address: 200 Heisman Harbor, Michigan City, IN 46360
Location: New Buffalo and Michigan City
Distance From Chicago: About 1 hr 5 min to the Michigan City dock
Harbor Country Adventures is the region's one-stop shop for fun by land or by sea, running tours daily from Memorial Day through Labor Day. Here's the full lineup and what you can expect to pay:
The 100 Collection™ is proud to partner with Juniper Holiday + Home for the best Southwest Michigan Vacation Rentals. Owner Valerie Gangas created a collection of rentals that offer the best places to stay on Lake Michigan. Guests can expect richly designed living spaces, serene outdoor oases, and picturesque lake, forest, or blufftop views. Each unique space holds at least four people, making these homes great family options. Here are three favorites to book for your getaway.
The Moose House is a lodge-style retreat near New Buffalo Harbor with a Great Room stone fireplace, a chef's kitchen with a marble-top island, a 3-season sunroom, and even a screening room for movie nights. The main-floor primary suite has its own fireplace and jacuzzi tub, and the backyard adds a grill deck, fire pit patio, and large hot tub. Guests also get access to Camp Buffalo's pool, pickleball courts, playground, and clubhouse, all just minutes from downtown New Buffalo's restaurants, galleries, and beaches.
Perfect for big groups, Dunegrass Path is a lakefront estate on 26 wooded acres with its own private stretch of Lake Michigan beach reached by a wooden walkway. The home pairs vaulted ceilings and floor-to-ceiling windows with a chef's kitchen, two fireplaces, an indoor sauna, and a pool and hot tub combo out back. With a king suite, five queen rooms, and a bunk room, everyone from grandparents to grandkids gets their own space.
Featured on HGTV and in Lonny, Cottage Living, and Bungalows & Cottages magazines, Leo Cottage was designed by Kate Marker Interiors and sits in the heart of Union Pier, a short walk from the beach. Patterned floors, vaulted ceilings, exposed beams, a clawfoot tub, and wood-burning fireplaces give the two queen bedrooms and bunk room plenty of character. Outside you'll find an award-winning garden, a private hot tub, a fire pit, a screened-in gazebo, and bikes and beach chairs ready for lake days.
With world-class wineries, waterfront dining, barns full of antiques, and endless ways to get out on the lake, Southwest Michigan packs a full vacation into a short drive from Chicago. When you're ready to make it happen, book your stay with Juniper Holiday + Home and settle into the perfect Lake Michigan home base for your trip.
