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Explore Chicago to Milwaukee in One Day

Viewed by 85 travelers

Day 1: City Adventure

Chicago, USA to Milwaukee, USA on January 20, 2025

7:30AM

Breakfast at Lou Mitchell's

Start your day with a hearty breakfast at Lou Mitchell's, famous for their fluffy pancakes and freshly squeezed orange juice, providing the perfect fuel for your adventure.
Head to the restaurant located at 565 W Jackson Blvd, just a short ride from your hotel.
USD20, 1 hour

9:00AM

Visit Millennium Park

After breakfast, take a stroll through Millennium Park to admire the iconic Cloud Gate sculpture and the stunning gardens, soaking in the winter atmosphere.
Walk south from Lou Mitchell's for about 15 minutes or take public transit.
Free, 1 hour

10:30AM

Departure to Milwaukee

Catch the Amtrak train from Chicago Union Station to Milwaukee, enjoying the scenic views along the way.
Head to the train station, board the Amtrak Hiawatha service.
USD30, 1.5 hours

12:00PM

Lunch at Steny's

Once in Milwaukee, head to Steny's for a classic Wisconsin meal featuring cheese curds and craft beer, a quintessential local experience.
Take a quick cab or rideshare from the train station to 800 S 2nd St.
USD25, 1 hour

1:30PM

Explore the Milwaukee Art Museum

Visit the stunning Milwaukee Art Museum, renowned for its architectural marvels and exceptional collections, making for an enriching afternoon.
Walk to the museum nearby, approximately a 15-minute stroll along the lake.
USD19, 2 hours

3:30PM

Relax at Lakefront Brewery

Head to Lakefront Brewery for a relaxing atmosphere, where you can enjoy a guided brewery tour and taste some local craft beers.
Take a quick rideshare, about 10 minutes from the art museum.
USD15, 1.5 hours

5:00PM

Dinner at The Safe House

Conclude your day with dinner at The Safe House, a spy-themed restaurant that will delight you with its quirky ambience and delicious meals.
It’s a short cab ride from Lakefront Brewery to your dinner destination at 779 N Front St.
USD30, 1.5 hours

7:00PM

Return to Chicago

After a fulfilling day, catch the return Amtrak train back to Chicago, reflecting on the wonderful experiences you've had.
Head to the Milwaukee train station for your ride back.
USD30, 1.5 hours
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