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1-Day Adventure: Chicago ORD to Milwaukee via Pleasant Prairie Premium Outlets

Day 1: Shopping and City Sights

Pleasant Prairie, USA on January 20, 2025

8:00AM

Breakfast at Egg Harbor Cafe

Kick off your day at Egg Harbor Cafe, where you can indulge in their famous cherry vanilla pancakes or a classic omelette to fuel your shopping adventure.
Drive from Chicago ORD, approximately 1 hour.
USD15, 1 hour

9:30AM

Shopping at Pleasant Prairie Premium Outlets

Spend the morning exploring the Pleasant Prairie Premium Outlets, home to a variety of brand-name stores offering fantastic discounts.
Walk through the outlet mall.
Free (purchases vary), 3 hours

12:30PM

Lunch at Olive Garden

After shopping, enjoy a delightful lunch at Olive Garden, where you can treat yourself to their famous breadsticks and a comforting bowl of minestrone soup.
5-minute drive from the outlets.
USD20, 1 hour

1:30PM

Drive to Milwaukee

Head to Milwaukee, soaking in the scenic views as you drive approximately 30 minutes to the vibrant city known for its beer and beautiful lakefront.
Drive to Milwaukee, 30 minutes.
USD10 (gas estimate), 30 minutes

2:00PM

Visit Milwaukee Art Museum

Explore the stunning Milwaukee Art Museum, famed for its innovative architecture and impressive collections spanning centuries.
Drive to the museum, 10 minutes.
USD19 (admission), 2 hours

4:30PM

Stroll along the Milwaukee Riverwalk

After the museum, take a scenic stroll along the Milwaukee Riverwalk, absorbing the local art, culture, and delightful river views.
Walk from the museum.
Free, 1 hour

5:30PM

Dinner at The Capital Grille

End your day with a sumptuous dinner at The Capital Grille, where you can enjoy a perfectly cooked steak and expertly paired wines to wrap up your adventure.
Drive 10 minutes to the restaurant.
USD50, 2 hours

7:30PM

Evening in Milwaukee

Spend your evening soaking in the vibrant nightlife of Milwaukee or relax with a drink at a local bar before heading back to Chicago.
Explore walking around downtown.
Varies, As long as desired
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