5 Winter Weekend Escapes Around Chicago

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5 Winter Weekend Escapes Around Chicago
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Main Street, Galena, Illinois. (Photo courtesy of flickr.com/photos/moistpics3.)

Chicago is a great city filled with renowned art venues, world-class restaurants, and an energetic nightlife scene. With so many awesome things to do here, why would anyone ever want to leave? Well, while Chicago is certainly a fun place to live, it is also one of the most densely packed cities in the U.S. Crowding and congestion are constant, so stress is high, and true relaxation is tough to come by. Fortunately, Chicago is surrounded by dozens of quick escapes that will make you feel like you're a world away. Here are a few examples for a winter weekend getaway.

Galena, Illinois, is roughly 160 miles from Chicago, and it has lots to offer, whether you're looking for a romantic weekend for two, winter fun, or you just want to warm up around the fireplace with close friends. Eagle Ridge Resort & Spa offers all of this and them some. Visitors can dine, spa, ice skate, ski, sled, and more during the winter months, and crowds are minimal. Other great places to stay include The Irish Cottage Boutique Hotel (just a short walk from Main Street shops and restaurants) and the DeSoto House Hotel, which is located on Main Street right in the middle of all the action.

If you're interested in history, Galena is home to a number of grand historic buildings, such as the Ulysses S. Grant Home, Felt Manor, The Dowling House, and more. For more information about visiting Galena and guided tours, go to Galena.org.


Lake Geneva, Wisconsin, is less than 80 miles from Chicago. During the winter months, visitors will find an abundance of outdoor activities, from skiing and snowshoeing to ice skating and ice fishing.

This picturesque city with a population of less that 8,000 is home to an impressive number of posh hotels, but one of the best places to stay is Grand Geneva Resort & Spa. Besides stunning views of snow-covered landscapes during the winter months, Grand Geneva has a full spa, a health club, 18 downhill slopes, scenic cross-country ski trails, and a collection of luxury accommodations and condos. Although you'll find plenty of places to eat around Lake Geneva (try Grandview Restaurant and Lounge), Grand Geneva houses a steakhouse (Geneva ChopHouse), an Italian Restaurant (Ristorante Brissago), and more. For more information about Lake Geneva, visit the Lake Geneva Area Convention & Visitors Bureau.

Sheboygan, Wisconsin, is a bit farther away than Lake Geneva at over 140 miles from Chicago, but you can get there in a little over two hours. If you have two full days to spare, visit Blue Harbor Resort (it sits on beautiful Lake Michigan), the Village of Kohler and John Michael Kohler Arts Center, and the Riverwalk. The Riverwalk features a variety of bar and grill restaurants, shops, and a cute Harbor Winds Hotel. Even during the winter months, a stroll along the lake or river is so beautiful, you'll forget it's 25 degrees. In addition to a gorgeous lakefront and the Riverwalk, Sheboygan has a lively downtown area with local favorites such as the 8th Street Ale Haus (1132 N. Eighth St.), which serves excellent pub grub along with an extensive collection of craft beers and imports, and favorite restaurants such as Trattoria Stefano.

Kenosha, Wisconsin, is just over 66 short miles from Chicago, and like some of the other getaways on this list, it sits on the shores of Lake Michigan. Visitors can choose from a number of chain hotels or a vacation rental. Things to do include riding Kenosha's electric streetcar along the Lake Michigan shore, ice skating at RecPlex Ice Arena (in Pleasant Prairie -- a 15-minute drive), Winter Harbor Market, and more. Kenosha's Winter Harbor Market is situated near the city's lakefront. Visit the Kenosha Area Convention and Visitors Bureau for a full list of winter activities.

Milwaukee is just another city, right? True, Milwaukee is a city, but even at around 598,000 residents, it's still much smaller than Chicago, and the pace is quite a bit slower. So if you're looking for a place where you can enjoy the art and culture scene at a much less hectic pace, Milwaukee is the perfect city. Leave at noon on a Friday, and you'll be in Milwaukee by 2 p.m.

Check into one of Milwaukee's many luxury hotels, such as The Pfister (with Well Spa & Salon) or The Iron Horse. Then, head out to a local favorite for dinner at Zarletti at 741 N. Milwaukee St. After dinner, head over to Indulge, a wine room at 708 N. Milwaukee St. Consider sleeping in Saturday morning, then when you're well-rested, head to the lakefront, where you'll find the Milwaukee Art Museum. Wear comfortable shoes, because you'll be there all day, and you'll likely spend an hour admiring the views of Lake Michigan, which is just as beautiful in December as it is in July.

The above are just a few recommendations for quick winter getaways for Chicagoans. What other destinations can you recommend?

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