Charming Towns to Visit for the Weekend

Looking to get out of Chicago for a peaceful weekend without going too far? We’ve got you covered. Here are the top picks for charming small towns that offer the perfect getaway.

Galena, IL

With sprawling golf courses, historic museums, and incredible wineries, Galena is our first choice for a weekend trip out of the Windy City. Approximately three hours away from the city, Galena offers the quintessential small-town feel with charming shops and restaurants.

For an overnight trip, the Aldrich Guest House is the perfect option. This bed & breakfast offers award-winning breakfast options set in a modern and elegant decor.

Spend the day exploring the Galena River Trail which offers six sprawling miles of stunning nature. For another activity, head to the Galena Cellars Winery & Vineyard. Take a tour and sip a glass of wine while you relax on the wraparound deck that overlooks the lush vineyard.

Oregon, IL

For an exceptional nature retreat and fine dining, plan a special weekend in Oregon. Delightful lunch and dinner options include La Vigna, The Blackhawk Steak Pit, and Jay’s Drive-In. For the best place to stay, Airbnb has a variety of cozy cottages and cabins to choose from in the area. For your second day of the trip, wake up and head to Bela’s Cafe — the charming breakfast spot that’s serving up all-around satisfying comfort food. After, head to the Black Point Estate for a morning tour of the grounds overlooking the lake.

Nauvoo, IL

Residing along the peaceful Mississippi River, this charming small town in McHenry County is the perfect location for a getaway weekend. Known for its historical and cultural significance, visitors have a variety of options for activities from lovely wine tours to vibrant bars and restaurants. After walking around town and taking a tour of the historic sights, head to Baxter Vineyards & Winery, the oldest vineyard and one of the best family-operated wineries in the area.

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