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Travel AI

5 Days Road Trip from Chicago to Milwaukee Itinerary

Last updated: 2024 Jun 14

Journey to Milwaukee

Morning

Start your road trip from Chicago to Milwaukee early in the morning. Enjoy a leisurely drive and take in the scenic views along the way. Upon arrival in Milwaukee, have breakfast at Blue's Egg, known for its delicious and hearty breakfast options.

Afternoon

After settling in, head to American Family Field (Miller Park) for a tour of this iconic baseball stadium. It's a must-visit for sports enthusiasts and offers a behind-the-scenes look at the home of the Milwaukee Brewers.

Evening

For dinner, visit Sanford Restaurant, a highly-rated fine dining restaurant offering exquisite dishes. After dinner, explore the Historic Third Ward, known for its vibrant nightlife and historic charm.

Bedtime

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Exploring Downtown Milwaukee

Morning

Begin your day with breakfast at Comet Cafe, famous for its comfort food and relaxed atmosphere. Then visit the Milwaukee Art Museum, which boasts an impressive collection of art and stunning architecture.

Afternoon

Have lunch at The SafeHouse, a spy-themed restaurant that's fun for all ages. Afterward, take a stroll along the Milwaukee Lakefront Trail, offering beautiful views of Lake Michigan.

Evening

Enjoy dinner at Bacchus - A Bartolotta Restaurant, known for its elegant dining experience. Post-dinner, catch a show at the historic Pabst Theater, one of Milwaukee's oldest and most beautiful theaters.

Bedtime

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Cultural and Historical Insights

Morning

Start with breakfast at Honeypie Cafe, renowned for its homemade pies and hearty breakfasts. Visit the fascinating Chudnow Museum of Yesteryear to learn about life in early 20th-century America.

Afternoon

Lunch will be at Tre Rivali, offering Mediterranean-inspired dishes. Post-lunch, explore the iconic Milwaukee City Hall and take some time to appreciate its architectural beauty.

Evening

Dine at Ardent, an upscale restaurant that offers innovative cuisine. After dinner, enjoy some local craft beers with a tour of the famous Lakefront Brewery.

Bedtime

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Outdoor Adventures

Morning

Have breakfast at Cafe Benelux, which offers European-inspired dishes. Spend your morning exploring the beautiful landscapes of Lake Park. It's perfect for hiking or simply relaxing amidst nature.

Afternoon

Grab lunch at Harbor House, known for its seafood and stunning lake views. In the afternoon, visit the historic lighthouse at North Point Lighthouse. The view from here is breathtaking.

Evening

Dinner will be at Ristorante Bartolotta dal 1993, an Italian restaurant that serves authentic cuisine. End your day with some fun activities at Bounce Milwaukee, an indoor entertainment center perfect for all ages.

Bedtime

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Final Day in Milwaukee

Morning

Start your last day with breakfast at Engine Company No 3 which offers farm-to-table dishes in a unique setting. Then embark on Milwaukee Local Food Tour to sample some of Milwaukee's best local foods.

Afternoon

For lunch visit The Vanguard known for their creative sausages and poutines then enjoy exploring more hidden gems with Milwaukee Scavenger Hunt Adventure. This interactive activity will take you through various landmarks around town.

Evening

Conclude your trip with dinner at Odd Duck where you can savor small plates inspired by global flavors before heading back to Chicago.

Bedtime

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