Quick Milwaukee Getaway With A Twist

Quick Milwaukee Getaway with a Twist perfectly sums up my 48-hour trip from Chicago. As a Chicago local now living in the UK, I had my family visiting the Windy City and wanted to give them a little more since they did the long journey travelling across the pond. Milwaukee was the answer since it’s just an easy 90 minutes drive that feels like a little escape without the stress of a long road trip.

We discovered how this Midwest gem blends nature, history, waterfront charm, and great food all in one short getaway. From quiet beaches to historic towns, scenic trails, and lively summer concerts, Milwaukee shines brightest in the summer. With outdoor dining, festivals, and local culture in full swing, it’s a refreshing Midwest escape whether you’re a Chicago local or a visitor exploring the region. Here’s how to make the most of 48 hours in Milwaukee.

Quick Milwaukee Getaway with a Twist Table of Contents

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Plan Your 48 Hours In Milwaukee

Use this complete Quick Milwaukee Getaway with a Twist guide and get all the travel information, tips and recommendations you need to plan your visit or return visit to this family-friendly summer getaway from Chicago.

Flight	Stay	Do	Drive
Skyscanner	Agoda	GetYourGuide	Rentalcars.com

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Milwaukee 2-Day Guide Itinerary

Day 1: Evening Arrival

Dinner At The Bridgewater Modern Grill
Start your trip with a relaxing dinner along the riverfront. The modern American menu and cozy ambiance make it easy to unwind after your drive. Dining by the river is perfect for families who want a scenic start to their trip.

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Day 2: Trails, Historic Towns & Waterfront Wine

Breakfast At Sweet Joy
Start your morning in Milwaukee’s Bay View neighborhood at this Brazilian-inspired café. The food is fresh and flavorful, and the atmosphere is calm—perfect for a family breakfast before a day of exploring.

Morning Hike & Beach At Lions Den Gorge
The trail is easy and family-friendly. Bring a swimsuit, beach blanket, and snacks to enjoy the quiet beach at the end. It’s a peaceful spot to relax, take in bluff views, and have a little picnic with the family.

Lunch In Cedarburg, WI At 13 North
Cedarburg is a historic and charming town just a short drive from Milwaukee. 13 North offers a variety of food options with big portions that are perfect for sharing. The town’s preserved architecture and quaint shops make it a calm, enjoyable stop.

Explore Port Washington & Afternoon Wine At Cavelier
We explored Port Washington first which is a scenic waterfront town with a historic lighthouse, charming shops, and a welcoming harbor. Then we headed to Cavelier for a wine happy hour. They offer small bites, seasonal deals, and non-alcoholic options, all with a beautiful view of the water.

Free Summer Concert Before Dinner
Before dinner, check out a free summer concert at Chill on the Hill in Humboldt Park. Most concerts are family-friendly, budget-friendly, and a fun way to experience Milwaukee’s summer culture.

Stay up to date with latest summer schedule.

Dinner At Dorsia – Pasta Flight
Dinner here is a family favorite. Portions are generous, so ordering three pastas is perfect to share, with a side or small pizza to round out the meal. Outdoor seating is great for evening people-watching, where you might spot some colorful characters.

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Day 3: Coffee, Waterfront Fun & Trails

Breakfast At Pilcrow Coffee
Pilcrow Coffee is a coffee lover’s dream. Their cafecito flights rotate seasonally, but they also offer classic drinks and light bites. If you’re working while visiting, it’s a comfortable spot to set up for a bit.

Lunch At Barnacle Pub
Don’t be fooled by the industrial surroundings, Barnacle Pub is lively, welcoming, and feels like a hidden beach shack. Right on the water, the food is fresh and tasty, making it a fun lunch stop for families.

Afternoon Beach Time At Atwater Park
Relax at this clean, family-friendly beach. Swim, sunbathe, or just enjoy the summer sun. It’s the perfect way to end a day of exploring.

Bonus Activity: 7 Bridges Trail
If you have energy left, take a stroll along the 7 Bridges Trail in Grant Park. Scenic river views, bridges, and quiet spots make this a peaceful, scenic way to enjoy Milwaukee before heading home.

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Bonus Experiences & Tips For Chicago Families

• Brewers Game: Experience a summer baseball game at Miller Park. Even if you’re not a baseball fan, the family-friendly atmosphere and stadium snacks make it a fun outing. Book your tickets in advance.
• Beer Tours: Adults can enjoy tastings, while kids explore the brewery spaces and learn about the city’s history. My top pick, the Original Milwaukee Guided Brewery Tour.
• Bike The Lakefront: Rent bikes and ride along Lake Michigan. The scenic trails and waterfront views are perfect for active families. Rent your bike today or consider a kayak rental to get onto the water.
• Harley Davidson Museum: Dive into American motorcycle history with interactive exhibits that engage kids and adults alike. Check out the Harley Davidson Museum tours available.
• Local Events & Summer Festivals: Keep an eye on outdoor concerts, markets, and festivals. Many are free or low-cost and showcase Milwaukee’s vibrant summer culture.
• If visiting with a family consider an apartment or home rental to have amenities like a kitchen, parking, laundry or even onsite gyms. We found our condo accommodation using Agoda.

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Extra Spots To Consider For Food

• Lakefront Brewery: Classic Wisconsin dishes like cheese curds, bratwursts, and frozen custard.
• Joy Ice Cream Social: Fun desserts with ice cream flights and sweet treats.

TIP: Give these local classics a try: Cheese curds, bratwurst, and frozen custard. Milwaukee/Wisconsin staples.

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Want to discover where else you can visit in America’s midwest?

See my Travel Guide Section for tips and recommendations for other bordering cities like Chicago. Learn how to get there, where to stay, eat and what to do!