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The Best Weekend Trips Within a Few Hours of Chicago

Hop in the car, and you can get to any one of these five destinations in less than three hours.


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While Chicago is known for its bitter cold winters, it’s really an exceptional city in any season. From jogging along the lakefront trail to a seemingly endless stretch of beer gardens and foodie hotspots with tea light-lined patios, the locals have it made in the summer months. But in the fall and winter, even as the temperatures drop, the architecture is no less striking and their culture scene no less eclectic and inviting.

Attributes aside, who doesn’t love a weekend getaway, just as a welcome change of scenery? Here, the five best weekend trips from Chicago, all within three hours of the city.

Lake Geneva, Wisconsin

Arguably the top choice for a Chicago mini-break, Lake Geneva, Wisconsin is only an hour and a half drive from the city. Stay at The Abbey Resort, right on the lake, and have dinner on your first night at the hotel, where their award-winning pitmaster serves up barbecue at the lakeside venue. On Saturday morning, pop over to Great Eggs, a new breakfast spot, where you can dine in their charming garden. Spend some time walking along the Lake Geneva Shore Path, a 26-mile loop around the perimeter of the lake, or pull up to Big Foot State Beach Park for a day in the sun.

You can also visit the adjacent Delavan Lake; if you’d prefer to stay in the quieter area of Geneva while still soaking in the waterfront views, stay at Lake Lawn Resort, on the shores of Delavan. Or just treat yourself to a massage at Lake Lawn Resort’s Calladora Spa before heading back to town, where you can have dinner al fresco at Pier 290—reserve ahead to sit in view of the water by a crackling fire pit.

Saugatuck, Michigan

Known as a distinctively queer-friendly community (with more than a 100 local businesses run by LGBTQ owners) and for their proximity to ever-popular Oval Beach, Saugatuck is really the perfect summer destination. Visitors can spend all day on the shores of Lake Michigan at Oval Beach, renting kayaks or sailboats, or bringing their lounge chairs and sandcastle fixings for a family beach day. Saugatuck is far from just a town for beach goers; culture seekers should visit Ox-Bow School of Art & Artists’ Residence, where they have impressive art fairs and showcases. The town is also known for their undulating sand dunes, and you can book a guided dune ride with Saugatuck Dune Ride. For guests looking to eat as the locals do, check out GROW Cafe + Bistro for brunch, grab sandwiches to eat at the beach at Farmhouse Deli & Pantry, and take your morning coffee at Uncommon Coffee Roasters. As for luxury accommodations, choose from two cozy bed and breakfast-style boutique hotels: Wickwood Inn and Hotel Saugatuck.

Indianapolis, Indiana

Swap out one city for another and head to the Circle City, just three hours away for Chicagoans. Take a long walk through downtown Indy, catch some live music at Hi-Fi Indy, and venture to see the public art installations put on by the Arts Council of Indianapolis. For a memorable night on the town, have dinner on the patio at Bluebeard, where their menu changes daily based on the farm-fresh ingredients they get their hands on. Or spend your evening at the Fountain Square Theatre Building; it was built in 1928 but has been renovated to feature a bowling alley and a rooftop garden where guests can sip cocktails and nosh on pizza and light bites. In terms of where to spend the night, the city has some higher-end hotels with authentic Indy accents, like the industrial-chic Ironworks Hotel Indy (don’t forget to check out their second-floor terrace hangout, Provision), or The Alexander, A Dolce Hotel, a boutique hotel downtown known for featuring commissioned works of high-end art from locally and internationally recognized talents.

Kohler, Wisconsin

A weekend trip to Kohler is all about kicking back at The American Club Resort, an American Express Fine Hotels & Resorts partner. Stay in your own luxury cabin as part of the Private Cabins at Destination Kohler program, or book a room at The American Club main property, “a five-star, five-diamond hotel that has stood as an icon of gracious hospitality for 100 years.” Dine within The American Club at The Wisconsin Room, for farm-to-table fare, at The Greenhouse, for lunch or afternoon tea, or The Winery Bar, which offers a 1000-bottle wine selection and an expansive array of fine Wisconsin cheeses.

While in Kohler, hit the boutiques at The Shops at Woodlake, or explore their vibrant art scene at Kohler Design Center, where admission to the multi-level showcase is free and they curate events for the public, and John Michael Kohler Arts Center. Whether you’re coming to Kohler for a romantic weekend with your partner or a family trip with the whole brood in tow, there’s plenty to do outside in any season, from snowshoeing in the winter to kayaking on Sheboygan River in the summer—and all of these activities can be arranged through Destination Kohler.

Grand Rapids, Michigan

Grand Rapids is having a real moment as an American city—evidently, they heard about Austin’s ultra-hip reputation and want in. In all seriousness, Grand Rapids is a perfect city destination for Chicagoans looking for a little less congestion but an ample culture scene. First off, this is Beer City USA, so a brewery tour is in order; start at the legendary Founders Brewing Co., before heading to sample the more Belgian and French-tending beer at Brewery Vivant, the hazy IPAs and Puerto Rican fare at City Built Brewing, and the wares at Brass Ring Brewing, serving English-style ale in a space meant to be an homage to Bukowski (though, what bar isn’t, really?). While immersing yourself in the Grand Rapids atmosphere, be sure to visit Grand Rapids Art Museum to see the Andy Warhols, grab an espresso at Madcap Coffee, and try the fresh-churned ice cream at Love’s in Grand Rapids Downtown Market. Your itinerary in Grand Rapids might be action packed—specifically with food and beer venues—but take time to unwind at JW Marriott Grand Rapids, a 23-floor luxury tower with excellent treatment offerings at The Spa at the JW Marriott.


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