Trip Ideas Weekend Getaways water outdoor sky skyline City daytime Sea cityscape urban area metropolitan area cloud skyscraper tower block horizon metropolis Downtown Harbor River Ocean marina Boat port coastal and oceanic landforms bay building calm Coast channel day
Weekend Getaways

8 Best Chicago Weekend Getaways

With slick boutiques, a handful of the country’s hottest kitchens, and more than a few rapidly-evolving neighborhoods, Chicago to-do lists are easier to add to than cross off. But given it’s within driving distance of so many other Midwestern gems, Windy City residents should step outside Chi-Town limits every once in awhile. Here, 8 easy weekend getaways, from midsize cities like St. Louis, Missouri, to quaint, unincorporated villages like Saugatuck, Michigan.

Road Trips Trip Ideas Weekend Getaways tree grass outdoor road leaf Nature yellow autumn woody plant infrastructure water plant Forest path scene way sky biome landscape reflection asphalt temperate broadleaf and mixed forest wooded woodland surrounded traveling
Road Trips Trip Ideas Weekend Getaways sky outdoor water pier scene wood house Sea dock cottage Coast cloud River Lake
Trip Ideas Weekend Getaways tree outdoor grass home house property cottage real estate log cabin estate landscape lawn farmhouse backyard evening hut plant outdoor structure facade
Trip Ideas Weekend Getaways tree outdoor grass Nature home property house cottage estate real estate residential area plant leaf Garden suburb landscape neighbourhood path yard landscaping walkway sky lawn outdoor structure backyard farmhouse park plantation land lot residential stone lush surrounded
Trip Ideas Weekend Getaways table plate food cup fries hamburger fast food dish junk food fried food brunch french fries Drink cuisine sandwich buffalo burger side dish cheeseburger breakfast finger food meal breakfast sandwich veggie burger american food snack food beef on weck full breakfast slider recipe
Road Trips Trip Ideas Weekend Getaways tree outdoor grass water promontory Coast Nature aerial photography bird's eye view hill hill station green mount scenery lush sky hillside plant Sea land lot cape grassy overlooking bushes Garden
1

Door County, Wisconsin

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.

Trip Ideas Weekend Getaways outdoor flower landmark building fountain water feature park Garden memorial monument crowd
Trip Ideas Weekend Getaways indoor wall room Living sofa floor property living room ceiling home estate interior design real estate Design furniture mansion Suite cottage apartment decorated flat Bedroom area
Trip Ideas Weekend Getaways tree outdoor sky water bench grass Lake Nature wooden park meadow overlooking chair seat flower pond surrounded lush
Trip Ideas Weekend Getaways grass tree outdoor sky metropolitan area Nature reflection green daytime skyline City water leaf cityscape urban area River real estate estate residential area Lake landscape pond meadow bayou skyscraper mount scenery park metropolis lush Downtown bank reservoir grassy computer wallpaper leisure watercourse botanical garden wetland hillside
2

Indianapolis, Indiana

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.

Trip Ideas Weekend Getaways sky outdoor water Nature Beach Sea Coast shore body of water coastal and oceanic landforms sand Ocean horizon bay vacation promontory headland wave cape tourism sandy
Trip Ideas Weekend Getaways indoor pan
Trip Ideas Weekend Getaways indoor person wall ceiling people café coffeehouse restaurant interior design several
Trip Ideas Weekend Getaways building outdoor tree ground neighbourhood Town brick street scene sidewalk way City real estate house facade mixed use alley window
3

Saugatuck, Michigan

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.

RELATED: 9 Best Hotels in Chicago

Trip Ideas Weekend Getaways sky outdoor grass Nature cloud tree daytime Garden plant tourist attraction landscape botanical garden tourism leisure park recreation flower shrub landscaping computer wallpaper clouds day stone
Trip Ideas Weekend Getaways tree outdoor grass Garden statue leaf plant monument park landscape shrub landscaping botanical garden memorial sculpture lawn
Trip Ideas Weekend Getaways sky water outdoor metropolitan area scene City skyline cityscape skyscraper urban area reflection tower block Harbor landmark daytime waterway metropolis condominium Downtown building River real estate tree mixed use bridge

Top Images courtesy of Frederik Meijer Gardens & Sculpture Park

4

Grand Rapids, Michigan

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.

Trip Ideas Weekend Getaways sky outdoor grass Architecture building house corporate headquarters facade real estate
Trip Ideas Weekend Getaways table indoor plate wooden dishware tableware food dish cookware and bakeware breakfast meal brunch flavor recipe set several
Trip Ideas Weekend Getaways ceiling indoor table floor person restaurant people cafeteria several dining room
Trip Ideas Weekend Getaways outdoor sky water cityscape City skyline metropolitan area daytime landmark urban area metropolis River skyscraper reflection Architecture Downtown background cloud arch tower block fixed link horizon bridge evening dusk meteorological phenomenon building
5

St. Louis, Missouri

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.

RELATED: What to Do in Chicago Now

Trip Ideas Weekend Getaways tree outdoor house Nature home landmark building Architecture plant real estate mansion estate cottage sky outdoor structure facade plantation residential Villa City historic house Town surrounded
Trip Ideas Weekend Getaways indoor room floor Living living room chair interior design furniture Lobby home table estate dining room flooring window area decorated
Trip Ideas Weekend Getaways floor indoor chair room interior design Living home window house furniture living room
Trip Ideas Weekend Getaways sky outdoor water grass Nature body of water cloud Sea shore Coast tree Boat Ocean loch bay Lake landscape plant coastal and oceanic landforms horizon vehicle Beach tourism inlet River reservoir lake district bank day
6

Lake Geneva, Wisconsin

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.

Trip Ideas Weekend Getaways outdoor building mixed use City night Downtown signage advertising facade electronic signage outlet store car dealership sky sign
Trip Ideas Weekend Getaways person marketplace market public space bazaar people scene City retail shopping stall group crowd supermarket service
Trip Ideas Weekend Getaways water outdoor sky skyline City daytime Sea cityscape urban area metropolitan area cloud skyscraper tower block horizon metropolis Downtown Harbor River Ocean marina Boat port coastal and oceanic landforms bay building calm Coast channel day
7

Milwaukee, Wisconsin

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.

RELATED: The Weekender's Guide to Chicago

Trip Ideas Weekend Getaways sky outdoor property house home real estate building tree estate grass facade Villa plant mansion tourism
ambient lighting artistic artsy Bar bar seating distillery Hip industrial interior trendy Trip Ideas Weekend Getaways indoor floor ceiling building Lobby factory interior design retail stall tourist attraction
barrels distillery Trip Ideas Weekend Getaways whiskey vessel barrel indoor man made object wood guitar plucked string instruments wine Drink string instrument shape basement
distillery Drink drinks glasses people Trip Ideas Weekend Getaways whiskey whiskey tasting distilled beverage indoor alcoholic beverage alcohol whisky beer liqueur glass container
Trip Ideas Weekend Getaways outdoor building car road street neighbourhood Town transport luxury vehicle City vehicle motor vehicle urban area Downtown mixed use family car residential area tree parked lane driving house metropolitan area plant traffic traffic congestion Classic pedestrian metropolis sedan compact car facade subcompact car city car suburb carriage van
8

Galena, Illinois

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.

Want more?