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5 Weekend Trips from Chicago

Chicago might not be known for its proximity to majestic mountains, idyllic vineyards or spectacular seaside resorts. However, “The Paris of the Midwest” can claim picture-perfect rural landscapes, unique Midwestern towns and, of course, expansive Lake Michigan as neighbors. Inviting destinations in nearby states like Wisconsin, Michigan and Ohio beckon city slickers looking for a quick and convenient weekend getaway.

  • Milwaukee: Chicagoans may foster a healthy rivalry with our neighbors to the north, but that doesn’t keep us from visiting Milwaukee’s many attractions. It’s an easy 90-minute trip to rev up at the Harley-Davidson Museum, shop the bustling Milwaukee Public Market, take in the world-class Milwaukee Art Museum and tour the Miller Brewing Company. Plan a trip June 26-30 or July 2-7 to experience Summerfest, Milwaukee’s annual warm-weather bash showcasing national and local music, homegrown cuisine and, of course, Wisconsin-brewed beer.

  • South Haven, Mich.: Located two hours -- and a world away -- from Chicago, South Haven is a classic Lake Michigan resort town that draws Windy City residents like bears to honey. Of course, life centers around the shore in this beachside burg, but golf courses, hiking and biking trails and wineries are also outdoor draws. Visitors can also explore art galleries, antique stores and high-end boutiques that line the downtown streets and refuel at numerous restaurants serving locally inspired dishes.

  • Dearborn, Mich.: Home to the Ford Motor Company Headquarters, Dearborn is a Detroit suburb with a historic pedigree. Here you’ll find the Henry Ford Museum, filled with exhibits and examples of American ingenuity collected by the man himself; Greenfield Village, a replica of an 1800s village; and the Ford Rouge Factory Tour, which gives guests a first-hand glimpse into the car manufacturing process. This genteel town, which is four hours from Chicago, is also just 15 minutes from downtown Detroit, where attractions like the Automotive Hall of Fame, the Detroit Institute of the Arts and Comerica Park (home of the Detroit Tigers) all await.

  • Cincinnati: Cincinnati is a Midwestern city on the rise. Located four and a half hours from Chicago, the town is home to several recent building developments, including The Banks, a shopping and dining destination; the 45-acre Smale Riverfront Park; and a brand-new Horseshoe Casino featuring 400,000 square feet of gaming, dining and entertainment. Families will find much to explore at the renowned Cincinnati Zoo & Botanical Garden, the Newport Aquarium and the National Underground Railroad Freedom Center.

  • Cleveland: Ohio’s second largest city may be a five-hour drive from Chicago, but its array of activities makes it worth the trip. No visit would be complete without a stroll through the Rock and Roll Hall of Fame and Museum, where Rolling Stones: 50 Years of Satisfaction, a major exhibit detailing the ultimate rock band’s rise to fame opens on May 24. But Cleveland is more than just a destination for music-minded travelers. The city has recently raised its culinary profile, with notable restaurants, microbreweries and gourmet markets putting Cleveland on the foodie-approved map.

Find hotel deals in Chicago and other Midwest getaways at up to 50% off regular rates.

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Tips by

Deal Expert, Chicago
Thursday, March 28, 2013
See more Tips from
Wendy Wollenberg