8 Best Chicago Weekend Getaways

3 hours and 45 minutes by car from Chicago

With nearly 300 miles of Lake Michigan and Green Bay coastline, it only makes sense that Wisconsin's Door County picked up the nickname “The Cape Cod of the Midwest." Along with sandy sheltered beaches and rugged limestone cliffs, the peninsula is known to harbor extensive cherry orchards, hyper-local farm-to-table restaurants, and five state parks. If you only have time for one of the latter, don’t miss Whitefish Dunes, with its mile-long shore, towering dunes, and 14 miles of trails which crisscross the eastern end of the county. Of course, Wisconsin’s great outdoors can also be admired in a different, more adult way: on the Door County Wine Trail. Start your crawl in southern Algoma, and work your way through the region’s eight fruit-wine-producing vineyards ending in Fish Creek. Before the cherry and apple varieties get the best of you, head just a little further north to Wickman House in Ellison Bay. Situated in a village of just 165 people—and supplying its kitchen with produce from an onsite garden, the historic restaurant is as quaint as they come, but don’t let its looks fool you—the innovative menu (think: kimchi-stuffed grilled trout) is refreshingly big city.

3 hours by car from Chicago

Indianapolis may have more than a million less residents than Chicago, but make no mistake, the gentle-mannered Midwestern city is still “big” in its own way. Even beyond its sport mecca status, the Indiana capital has a lot under the hood, including a thriving culinary scene and renowned cultural institutions left and right. Of course, first-time visitors have to hit the Canal Walk—a three-mile loop that runs along Indy’s downtown waterfront. But once you’ve squeezed that in, make a meal-time detour to The Vanguard. With tempting large plates like half a fried chicken with honey slaw, peach butter, hot sauce, pickles, and a biscuit, the Broad Ripple restaurant weaves sometimes subtle, sometimes obvious southern flavors throughout its New American dishes. Before your weekend comes to end, drop by the IMA—aka the Indianapolis Museum of Art—for a lesson in African, American, Asian, and European art. The encyclopedic museum is filled with more than 54,000 pieces; with works from Neo-Impressionist paintings to 19th-century Irish embroidery, everyone’s bound to find something that interests them.

2.5 hours by car from Chicago

If you’re like us, the cornerstone of any great day is killer cup of coffee. In Saugatuck—a tiny beach town of roughly 1,000 on Lake Michigan’s eastern shore—Saturday’s are best started with cold brew or Costa Rican drip from Uncommon Coffee Roasters. Caffeine safely secured, make for Oval Beach, a pristine public stretch just minutes from another one of the town’s main attractions: Mount Baldhead Park. Visitors who pant their way 300+ steps up to the top of Mt. Baldhead are rewarded with panoramic views of Saugatuck and Douglas just to the south. Once you’re properly tuckered out, unwind at the Wickwood Inn. With an owner that doubles as a cookbook author, the romantic B&B prides itself on fresh (and free!) farm-to-table breakfasts, evening hors d'oeuvres, and sweet treats. Pair stellar onsite dining with French country decor, plush featherbeds, and roaring open fires, and you may just find yourself calling in sick on Monday to extend your trip a day or so.

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3 hours by car from Chicago

When it comes to Chicago weekend getaways, Michigan’s second-largest city is an easy choice. Just a 3-hour drive north (along Lake Michigan’s shore), Grand Rapids rolls out the welcome mat with a surprising number of acclaimed art and history institutions, and more than 60 craft breweries (which lend it its “Beer City” moniker). While you’re in town, you’ll want to grab a bite at one of Downtown Market’s 21 vendors (think: Neapolitan-inspired pizzas and slow BBQ) and follow it up with a drink at Brewery Vivant. Go for a Plein de Vie pour like the Harvest Breed or Stone Fruit Sour to get a taste of something traditional; undergoing wild fermentation, the series pays homage to early Belgian brewing processes. Once you’ve satisfied your epicurious side, take a drive to the outskirts of town to spend an afternoon at Frederik Meijer Gardens & Sculpture Park. With 158-acres of indoor and outdoor sculptures (including a piece from Dale Chihuly), highly-curated gardens, and exhibits of works from illustrious French artists like Auguste Rodin and Edgar Degas, it’s easy to lose track of time.

4.5 hours by car from Chicago

St. Louis may play second fiddle to nearby hubs like Chicago and Philly, but the second-tier city is worthy of at least one of your weekends. Last spring, Vicia—a veggie-centric spot with casual counter-service lunches, a la carte dinners, and 15-course tasting menus—made waves when it opened with STL native and former Blue Hill at Stone Barns chef de cuisine Michael Gallina at the helm. Drop by the lauded kitchen—it’s topped many best 2017 openings lists—for wood-fired family dishes like milk brined cauliflower with romesco sauce and curried almonds, and Berkshire pork with grilled apple puree. Once you’ve overstuffed yourself, skip the Arch and head for a walk at Laumeier Sculpture Park in Sunset Hills. The free and open to the public park was one of the country’s first and largest, and today, it shows 60 large-scale works across 105-urban-meets-pastoral-acres.

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1.5 hours by car from Chicago

Give us a few days in Lake Geneva and we’ll spend the first at Black Point Estate and Gardens, an 1888 Queen Anne-style summer home that once belonged to Chi-Town brew mogul Conrad Seipp. Today, visitors come to relax on wicker chairs lining the wrap-around porch, explore the cottage's collection of Victorian furnishings, and stroll through its intimate gardens. To catch a glimpse of the resort town's other waterfront estates, walk a portion of the 21-mile-long, shaded Geneva Lake Shore Path. When it's time for dinner, off to Oakfire you should go. Start with imported burrata paired with grilled crostini before moving on to a wood-fired pizza— say, the Sorrento with arugula, shaved parmesan, mozzarella and prosciutto. There's also a bambini menu if you're day-tripping with picky kiddos.

1.5 hours by car from Chicago

Ask anyone about Milwaukee's major claim to fame and they'll likely tick off a laundry list of beer manufacturers—Schlitz, Pabst, and Miller among them. If you're looking for a beer-centric trip, there are always the typical tours and tastings, but might we suggest checking out a beer baron's Renaissance Revival-style estate? The Pabst Mansion is right downtown, full of Captain Pabst and his wife Maria's personal art collection as well as all the PBR merch you could ever want. For a different taste of the city, hit up the Milwaukee Public Market, where artisanal producers and demo kitchens serve everything from vegan Indian to made-to-order sushi.

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3 hours by car from Chicago

Galena may be a little bit of a hike from Chi-Town, but its charming, historic, quaint downtown feel (the population rings in at under 4,000) and chocolate-dipped cones from the American Old Fashioned Ice Cream Parlor (the vintage black-and-white awning is unmistakable) make it well worth the scenic drive. Main Street is the shopping thoroughfare of choice, so stick around long enough to bob in and out of its historic brick buildings housing a hundred or so boutiques, galleries, and cafés. Afterwards, head to the Blaum Bros. Distilling Co. and Cocktail Bar for a tour and a snarky drink like the Billy Fitz ("It's like Wrestlemania in a glass") with gin, fresh lemon, simple syrup, and lavender bitters before chomping down on some poulet roti or other German/French bistro-style grub at the husband-and-wife-run Fritz and Frites.