5 Best Short Road Trips from Chicago

Ahhh, the American road trip.

Pacific Coast Highway road trip

A tank of unleaded, wind in your hair, a playlist full of good music, unhealthy gas station provisions, and the open road. Growing up in the remote northwoods of Upper Michigan, road trips were an unavoidable necessity to reach what many would consider “civilization” (or even a real shopping mall). For me, road trips have always been synonymous with summertime and the ultimate benchmark of freedom, wanderlust, discovery and adventure. The following is my guide to the best road trip destinations within 3 hours of Chicago, for any season:

  1. Saugatuck/ Douglas- The Art Coast of Michigan (**CGT favorite)                                              
    • Road Trip Length: 2 hours 7 minutes, without traffic (141 miles)
    • Reasons to Go: Saugatuck, a picturesque beach town on Michigan’s West Coast, has received countless accolades for being a summer destination and made Travel & Leisure’s 2014 list for Most Romantic Fall Getaways. My choice for the perfect weekend getaway, Saugatuck offers travelers award-winning beaches, eclectic art galleries, a lively dining and drinking scene, and endless small town charm.
    • Detour-Worthy:
      St. Joseph, MI

      St. Joseph, MI

      • Fennville, Michigan: a quaint, even tinier town that is home to a winery; orchards; a local, craft hard cider mill; and a remarkable, locavore eatery specializing in rustic, farm-to-table fare.
      • St. Joseph, Michigan: AKA the “Riviera of the Midwest,” St. Joe’s is a delightful, little beach town that is worth a pit-stop for Silver Beach and its namesake Silver Beach Pizza alone.
      • The Lake Michigan Shore Wine Traildubbed the “Napa Valley of the Midwest,” the wine trail boasts over a dozen wineries and tasting rooms, some of which have limited seasonal hours.
  2. Milwaukee, WI                                                                                                                                          

    • Road Trip Length: 1 hour 30 minutes, without traffic (92 miles)
    • Reasons to Go: Because beer, cheese, and brats. And did I mention cheese and beer? That aside, Milwaukee is friendly, affordable, unpretentious and retains a small big-city feel. The city enjoys a prime lakefront location and offers great restaurants, watering holes, museums, historic architecture, and is a bastion of German culture. Also known as Brew City, or the “German Athens of America,” Milwaukee is a blast for a quick weekend away or even an overnight trip from Chicago. The birthplace of the classics (read: Pabst Blue Ribbon, Blatz, Schlitz) and Miller Brewing Company, Milwaukee is well-known for several smaller, regional breweries and microbreweries, Lakefront Brewing being my favorite.
    • Detour-Worthy:
      Mars Cheese Castle, Kenosha, WI

      Mars Cheese Castle

      • The Mars Cheese Castle: in Kenosha, WI, just off an I-94 exit, is an enormous castle- the veritable mecca of cheese. Mars Cheese Castle is chock full of, well, cheese (try the incredibly habit-forming garlic dill cheese curds), kitschy souvenirs, Wisconsin beer (New Glarus!), chocolate, and lots of sausage. Mars also houses a bakery, deli, and great little bar. PRO TIP: go to the bar… hang out and mingle with the patrons… snack on complimentary Ritz’s crackers smothered in pub cheese… wash them down with an expertly-prepared Bloody Mary with a beer back … thank me later.
      • Pleasant Prairie Premium outlets.
      • The Brat StopAlso, in keeping with the beer, cheese, and brat theme, check out the Brat Stop, located in Kenosha, WI. It is open 365 days a year and is world-famous and legendary. The website says so.
  3. Starved Rock State Park, IL                                                                                                                  

    • Road Trip Length: 1 hour 28 minutes, without traffic (90 miles)
    • Reasons to Go: A reprieve from the hustle and bustle of the city, Starved Rock is a nature-lover’s wonderland. Visitors to Starved Rock can enjoy wildlife, hiking, biking, canoeing, and cross-country skiing on 13 miles of trails. Located in Utica, Illinois, Starved Rock’s terrain of bluffs, forests, canyons, rivers, and waterfalls is a welcome departure from the flat, prairie topography that characterizes most of Illinois. Check into the Starved Rock Lodge for a place to crash in woodsy comfort.
  4. Grand Rapids, MI                                                                                                                                  


    • Road Trip Length: 2 hours 40 minutes, without traffic (178 miles)
    • Reasons to Go: Grand Rapids (& Lake Michigan’s Gold Coast) was named the Top
      Tarta de Chocolate Con Trufas at San Chez, Grand Rapids, MI

      Tarta de Chocolate Con Trufas, San Chez

      US Travel Destination for 2014 by Lonely Planet. Michigan’s second largest city is the epicenter of the American craft beer movement and, having been crowned Beer City USA and Best Beer Town, it is the vacation destination for beer-lovers. Don’t miss Founder’s Brewery, Brewery Vivant, The Mitten Brewing Company, and HopCat just to name a few. Stop in at Real Food Cafe for breakfast, and check out San Chez A Tapas Bistro & Cafe for a dinner of delectable small plates and vino. Bonus: Grand Rapids also enjoys close proximity to Michigan’s Gold Coast beach towns and wineries.

  5. Lake Geneva, WI                                                                                                                               

    • Road Trip Length:1 hour 25 minutes, without traffic (83 miles)
    • Reasons to Go: The classic quick jaunt from Chicago, Lake Geneva is a touristy resort town conveniently situated just over the Wisconsin border from the Land of Lincoln. Geneva Lake itself is a haven for water-sports enthusiasts, and on its shores, the town of Lake Geneva includes an array of dining options, golf courses, spas, and cutesy B&Bs and is replete with opportunities for rest, relaxation, and romance.

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