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.

1
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.

2
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.

3
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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