Whether you are arranging a day trip or booking an overnight stay, these picturesque getaways promise exquisite natural wonders, tranquil beaches and historic charm—just a short road trip from the Windy City. So pack your bags, hit the road and embark on an adventure-filled journey with scenic destinations, tasty treats and luxe shops around every corner.
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Located only an hour from the Windy City, this village is a hidden gem, with boutiques, galleries, coffee shops and art galleries housed by quaint historic buildings—many of which date back to the early 19th century. Guests can embark on birdwatching excursions, biking trips, hikes and strolls through the downtown area and join in for annual festivals and events, including the strawberry and apple festivals. Stop by local favorites, including bakery Apple Haus, Blue Fig Cafe and The Chatter Box gastropub.
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This breathtaking forest preserve has just what you need to explore the great outdoors, from trolley tours to waterfall cruises. With 18 sandstone canyons, lookout points to the Illinois River, water activities and more than 13 miles of hiking trails, guests can get their nature fix while enjoying eats, amenities and cozy accommodations at Starved Rock Lodge.
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Located along Lake Michigan’s southern shore, Indiana Dunes National Park is home to sandy beaches, hiking trails and soaring sand dunes, some towering 200 feet above the lake. The destination features local shops and restaurants, including Anderson’s Winery and Vineyard, Coffee Creek Farmer’s Market and Dune Land Pottery.
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With a sandy beachfront, historic mansions, popular shops and tasty eats, Lake Geneva is a relaxing destination to add to your itinerary. Stroll through the streets of Downtown Lake Geneva and visit galleries, coffee shops, antique stores and boutiques—such as SoHo Boutique, Circa and Lucca Lifestyle. Enjoy fare, libations and views from fine dining destinations, including Pier 290, Geneva Chophouse, The Grandview Restaurant and more.
See also: The Ultimate Guide To Galena
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Home to historic architecture, gardens, shops, dining spots and more, this destination is chock-full of spots for guests to explore, including Downtown South Bend, Studebaker National Museum, Potawatomi Zoo, The History Museum and East Race Waterway—ideal for whitewater rafting trips, kayaking and paddleboat excursions. Don’t forget to stop by the South Bend Chocolate Company to take home tasty mementos from your trip.
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From vineyards to art galleries, Allegan County boasts charming spots that showcase its natural beauty and rich history. Visitors can explore towns within the county, including Saugatuck and Douglas, with chic boutiques, antique shops and Kalamazoo River views. During your stay, visit Wild West Ranch for horseback trail rides, pay a visit to Brave Art Studios & Gallery to peruse exhibits and enjoy coffee and treats from Allen’s Farm Market Cafe and Bakery.
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Meander down Galena’s Main Street, known for its historic storefronts, artisan shopping destinations, restaurants, craft breweries and distilleries, including Galena Cellars Vineyard & Winery, Jamie’s Wine Studio of Galena and Blaum Bros Distilling Company—ideal for wine-tasting and sampling curated brews and spirits. The town is nestled in the Illinois countryside, with rolling hills, golf courses and serene parks, including Galena River Trail and Casper Bluff Land & Water Reserve.
See also: The 9 Best Art Museums To Visit In Chicago
Photography by: MICHAEL REGA / GETTY IMAGES
