With Chicago, Illinois being situated in the Midwest, there are an abundance of interesting towns and cities nearby. Take a break from this iconic city by escaping to one of the surrounding towns for a weekend full of relaxation and scenic views. Whether you choose to visit Michigan or Missouri for the weekend, these unique locations are just a short drive away from Chicago. Book a stay at an incredible vacation rental in Chicago today. Enjoy the rich history and charm of these surrounding rustic towns.

1. Galena, Illinois

A little over three hours west of Chicago sits the picturesque town of Galena. Several bed and breakfasts locations, such as Annie Wiggins and Aldrich Guest House, offer a relaxing and friendly environment distinct from the busy ambiance of normal hotels. Take a stroll on cobblestone streets with Victorian-style architecture and historic mansions highlighting your path.

Outdoor aficionados find the scenic hiking trails overlooking the Mississippi River a true delight, while a walk along the Galena River Trail provides beautiful views of local flora and fauna. Wine connoisseurs relax comfortably at Fergedaboudit Vineyard & Winery or enjoy grape stomping and modern art at Galena Cellars Vineyard & Winery. A diverse selection of restaurants complements this town, with French and German dishes on offer at Fritz and Frites Bistro, while Vinny Vanucchi’s “Little Italy” offers authentic Italian fare.

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2. New Glarus, Wisconsin

Known as “America’s Little Switzerland,” New Glarus gives you the heritage and cuisine of Switzerland without traveling across the globe. Three hours northwest of Chicago, this charming town features beautiful architecture reminiscent of Switzerland. Try to catch the notes of melodic yodeling and alphorns throughout the village from the window of your vacation rental. A trip during the right three-day weekend exposes you to traditional events such as the Wilhelm Tell Festival in June and Polka Fest in September.

Both Badger State Trail and Sugar River State Trail offer stunning views of the woods, rolling hills, and scenic meadows of New Glarus. For breakfast and lunch, enjoy farm-to-table dining at Cow & Quince for dishes featuring items prepared on-site, such as signature jams and cheeses. Puempels Olde Tavern offers delicious cocktails and cold beers, but a trip to New Glarus is incomplete without a visit to New Glarus Brewing Company. The signature beer of this brewing company is only sold in Wisconsin, so be sure to load up before you leave the state.

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3. Saugatuck, Michigan

The Lake Michigan shoreline elevates the Hampton-style ambiance of this beautiful town located three hours northeast of Chicago. Admire the artistic vibe of downtown Saugatuck with art gallery lined streets and gorgeous gardens. Although the main attraction is Oval Beach, Saugatuck Dunes State Park will excite your inner outdoorsmen. Marvel at the fresh water coastal dunes standing over 200 feet tall or trek the park’s diverse terrain from steep slopes to rolling hills.

Pick a meal to satisfy any craving with over 30 restaurants to select from in the area, but the true culinary gems are imbibed; Fenn Valley Vineyards offer a selection of wines, and Saugatuck Brewing Company let you brew your own beer. Music lovers rejoice for the Chamber Music Festival or Concerts in the Park during summer, which make a weekend getaway during this season more alluring.

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4. Mount Carroll, Illinois

Anyone who enjoys history will find the town known as the “New England of the Midwest,” both stimulating and engaging. Discover the small town of Mount Carroll located three hours west of Chicago to visit historic sites like the Carroll County Courthouse and the Nathaniel Halderman House and to take in structures that transformed the history of the town.

A hike in Mississippi Palisades State Park offers more than a breath of fresh air. The limestone caves and ancient cliffs are magnificent sights to see for any outdoor enthusiast. A trip to nearby Savanna offers an opportunity to catch a glimpse of a majestic eagle and other native species. Although the restaurant and bar scene is limited, make an excursion to Poopy’s for a laid-back atmosphere complemented by cold beers and tasty pub foods. If you feel adventurous, try the Big Poop Burger, for a delicious dish that tastes better than it sounds.

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5. Traverse City, Michigan

Located five hours northeast of Chicago, Traverse City delivers a winter wonderland complete with snowmobile rides, Nordic skiing, and snowshoe trails. If summer seems more appealing for a two-day vacation, select the right weekend to enjoy the Cherry Festival in July, the Traverse City Film Festival, or the Taste of Traverse City. With 35 miles of gorgeous scenic coastline, you can gaze at the natural beauty of this lovely town on a walk down the beach, or get out on the water with Traverse Tail Ship Company or Two Brothers Sailing Adventures.

For some playful fun, roll around in the sand at Sleeping Bear Dunes before watching a breathtaking sunset over the Leelanau Peninsula. Traverse City offers a plethora of restaurants, wineries and dining options, but if you love cherries, check out Cherry Republic for a menu with a touch of cherry in almost everything.

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6. Door County, Wisconsin

After a four hour drive north of Chicago, stop in Door County to experience a fish boil like none other from Pelletier’s Restaurant. Cherry pie is a popular treat in Door County, and Coffee & Tea has become the local favorite supplier. While a variety of wineries and breweries are a high-brow way to enjoy a drink, a visit to Kitty O’ Reilly’s delivers a relaxed atmosphere to enjoy a nightcap.

The heritage and traditions of this small town are unlike that of any other in the Midwest. Door County pulls you in with striking views of the shoreline, and the magnetic draw of various lighthouses including the historic Cana Island Lighthouse. The Door County Historical Museum educates visitors on the distinct history of Door County, while observation towers in Potawatomi State Park and Peninsula State Park provide a panoramic view of the natural scenery. Lovers of the outdoors find the enthusiasm for nature conservation refreshing, while a hike on Eagle Trail or a kayak excursion on Nicolet Bay Beach get your adrenaline pumping.

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7. Geneva, Illinois

Situated only one hour west of Chicago, Geneva offers a quick escape from the big city. Outdoor restaurants, such as Atwater’s and Fox Fire, line the Fox River for relaxing waterfront dining. Explore the Fabyan Forest Preserve for scenic views of nature or visit the on-site museum and historical windmill to engulf yourself in the rich history of Geneva. Take a guided walking tour of this quaint town to learn about the iconic architecture and Historic District. On your tour, pay close attention to sculptures and murals highlighting the lawns, buildings, and walkways.

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