Best Day Trips from Chicago

Chicago offers a wealth of nearby attractions that make for perfect day trips, allowing both locals and visitors to explore the rich history, culture, and natural beauty of the surrounding areas. From charming small towns to scenic landscapes, there's something for everyone within a short drive from the Windy City.

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One popular destination is the picturesque town of Galena, known for its well-preserved 19th-century buildings and vibrant Main Street lined with unique boutiques, art galleries, and delightful eateries. History buffs will appreciate a visit to the Ulysses S. Grant Home, while nature enthusiasts can explore the many trails and scenic overlooks at Horseshoe Mound. For those craving a lakeside retreat, Indiana Dunes National Park offers stunning beaches, sand dunes, and hiking trails just an hour away. Another option is the quaint town of Geneva, where visitors can stroll along the Fox River, enjoy the historic architecture, and browse through numerous shops and restaurants. Whether you're looking for outdoor adventures, historical sites, or simply a change of pace, the areas surrounding Chicago provide a diverse array of experiences that make for memorable day trips.

  • Madison, WI

    Madison, WI - Lakeside city, vibrant culture, university town, political hub.

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  • Milwaukee

    Milwaukee - Milwaukee: vibrant, historic, cultural, lakeside city with brewing heritage.

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Best Day Trips from Chicago

1.

Madison, WI

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Madison, Wisconsin, is a vibrant city known for its picturesque landscapes and rich cultural scene. Nestled between Lakes Mendota and Monona, it offers stunning waterfront views and abundant outdoor activities, including boating, kayaking, and scenic trails for hiking and biking. The city's iconic Capitol building, with its majestic dome, anchors a bustling downtown filled with eclectic shops, diverse dining options, and lively entertainment. Madison is home to the University of Wisconsin-Madison, adding a youthful energy and academic vibrancy. The Olbrich Botanical Gardens, with its stunning Thai Pavilion, and the Henry Vilas Zoo, a family favorite, are must-visit attractions. Renowned for its farmers' markets and festivals, Madison seamlessly blends small-town charm with urban sophistication.

Hotels

  • The Edgewater
  • Graduate Madison
  • AC Hotel by Marriott Madison Downtown
  • Hyatt Place Madison/Downtown
  • Hilton Madison Monona Terrace
  • HotelRED
  • DoubleTree by Hilton Madison Downtown
  • Best Western Premier Park Hotel

Dining

  • L'Etoile
  • Graze
  • Harvest
  • Tornado Steak House
  • Sardine
  • Marigold Kitchen
  • The Old Fashioned
  • Tempest Oyster Bar
  • Lombardino's
  • A Pig in a Fur Coat
Things to do

2.

Milwaukee

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Milwaukee, Wisconsin, is a vibrant city known for its rich brewing history, cultural attractions, and beautiful lakefront setting. Nestled along the western shore of Lake Michigan, it boasts the stunning Milwaukee Art Museum with its iconic, winged design by Santiago Calatrava. The historic Third Ward district offers a blend of trendy boutiques, art galleries, and renowned restaurants. Visitors can explore the Harley-Davidson Museum to delve into the legacy of the famous motorcycle brand. Milwaukee's lively festivals, such as Summerfest—the world's largest music festival—celebrate its diverse heritage. The city's RiverWalk, lined with public art and scenic views, is perfect for leisurely strolls. With its unique blend of old-world charm and modern attractions, Milwaukee offers something for everyone.

Hotels

  • The Pfister Hotel
  • Hilton Milwaukee City Center
  • The Iron Horse Hotel
  • Hyatt Regency Milwaukee
  • Kimpton Journeyman Hotel
  • Potawatomi Hotel & Casino
  • Marriott Milwaukee Downtown
  • Aloft Milwaukee Downtown

Dining

  • Sanford Restaurant
  • Lake Park Bistro
  • Harbor House
  • Ardent
  • Bacchus
  • A Bartolotta Restaurant
  • Odd Duck
  • Blue's Egg
  • Story Hill BKC
  • Mader's Restaurant
  • Ristorante Bartolotta.
Things to do

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