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Trip Ideas

7 Best Day Trips from Chicago

The Windy City has a lot going for it: world-renowned museums, an iconic skyline, one of the best culinary scenes in the States, welcoming Midwestern manners, and a ton of day-tripping options. Here, seven Chi-Town getaways that speak to the outdoorsman, foodie, and history geek in all of us.

A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.

See recent posts by Chelsea Stuart

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Holland, Michigan

2.5 hours by car from Chicago

The Netherlands meets the American Midwest in Dutch-settled (and aptly named) Holland, Michigan. Stepping into Nelis’ Dutch Village, you'll find typical European architecture, ringing carillon bells, costumed and clog-clad performers practicing folk dances, and 25,000 tulips straight from the homeland. Grab a treat to go (maybe some imported chocolates?) before heading to Crane's Pie Pantry Restaurant & Winery for lunch. This family-owned spot, on a private fruit farm just minutes from Lake Michigan, crafts specialized pies from local ingredients – but make sure to munch on something substantial, as you'll want to try a flight of cider or wine (there are 12 varieties of Crane's to choose from). Post-meal, Holland's iconic Big Red Lighthouse (or Holland Harbor Light, as it's officially known) is a must-see, especially at sunset. Grab a seat across the water on Holland State Park's beach or pier and watch as the sun bathes Lake Michigan in a warm pink glow, summoning small sailboats back into the channel.

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Lake Geneva, Wisconsin

1.5 hours by car from Chicago

Give us a day in Lake Geneva and we’ll be spending it at the 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.

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Photo by JWM-JWM via flickr


Springfield, Illinois

3 hours by car from Chicago

Chicago marks the start of Route 66’s east end, and it’d be a damn shame for anyone in the area not to take advantage. Starting in Chi-Town and mapping out a direct route to Springfield, your journey should take about three hours (plus a variable amount of time for detours and photo ops). Along the way, make pit stops for weird roadside attractions like the Abe Rail Splitter Statue and Paul Bunyan Hotdog Statue. You can even see the Americana theme through to the end of your cross-state jaunt with a greasy (in all the right ways) meal at Charlie Parker's Diner, which operates out of a Quonset hut in Springfield. The locally owned spot rocks a retro 50s aesthetic with black-and-white checkered floors, red vinyl booths, neon signs, and walls covered in album covers. Given the diner's look and menu – an all-day breakfast plus 'hot and hearty' options – it makes total sense that it was featured on Food Network's Diners, Drive-Ins and Dives.

RELATED: America's Best Long Weekend Getaways

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Oglesby, Illinois

1.5 hours by car from Chicago

Teeny-tiny Oglesby, Illinois, clocks in at just over four square miles with under 4,000 residents, but it attracts more than two million visitors each year to Starved Rock State Park. Thirteen miles of trails wind through sandstone bluffs, scenic waterfalls, and 18 different canyons, offering views of Illinois's flatlands all the while. If hiking isn't your forte, there are also trolley tours, water cruises, and horseback riding trails. Picnickers are always welcome, but, should you forget your pre-made sandwiches at home, it's just a 10-minute drive down the road to La Salle. We're partial to the tapas joint Pink Chihuahua and its steak and cilantro empanadas with cactus slaw or mango and brie quesadilla with pepper jelly.

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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.

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New Glarus, Wisconsin

2 hours and 45 minutes by car from Chicago

Wisconsin knows a thing or two about beer and cheese, so, naturally, any trip there should involve at least one or the other. New Glarus, “America’s little Switzerland,” ups the ante on both. The Maple Leaf Cheese & Chocolate Haus hawks local cheese, chocolate, ice cream, and wine, plus plenty of samples – all under one roof that makes our eyes grow bigger than our stomach. Five minutes down the street, you'll find New Glarus Brewing with six year-round microbrews and a rotating menu of seasonal ones (we like the sound of Coffee Stout). Top off your culinary exploration with an organic farm-to-table meal at Cow & Quince. The 1930s former grocery store serves a seasonal menu of breakfast, lunch, and dinner with foodie-friendly options like lemon bramble french toast and roasted ginger pork shoulder with kohlrabi and beet slaw.

RELATED: The Ultimate Book for Beer Snobs

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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 somepoulet roti or other German/French bistro-style grub at the husband-and-wife-run Fritz and Frites.

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