Epic Bachelor Party Road Trip in Chicago

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Day 1: Urban Adventure in Chicago

Chicago, IL, USA

9:00AM

Breakfast at Wildberry Pancakes and Cafe

Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes and Chicago-style dishes.
$$, 1 hour

11:00AM

Architecture Boat Tour

Embark on an architecture boat tour along the Chicago River to marvel at the city's iconic skyscrapers and learn about its rich architectural history.
$$$, 1.5 hours

1:00PM

Lunch at Portillo's

Enjoy a classic Chicago lunch at Portillo's, known for its famous hot dogs, Italian beef sandwiches, and chocolate cake shakes.
$, 1 hour

3:00PM

Visit Millennium Park

Explore Millennium Park and take iconic photos at the Cloud Gate sculpture, also known as 'The Bean.'
Free, 1.5 hours

6:00PM

Drive to Milwaukee, WI

Hit the road and make your way to Milwaukee, Wisconsin, for an exciting evening and night of bachelor party celebrations.
Gas money, 2 hours

8:00PM

Dinner and Nightlife in Milwaukee

Indulge in a delicious dinner at one of Milwaukee's renowned restaurants before experiencing the vibrant nightlife the city has to offer.
$$-$$$, Ongoing
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Day 2: Thrilling Day in Milwaukee and Lake Geneva

Milwaukee, WI, USA

9:00AM

Brunch at Blue's Egg

Start your day with a satisfying brunch at Blue's Egg, known for its creative egg dishes and scrumptious breakfast options.
$$, 1 hour

11:00AM

Harley-Davidson Museum

Explore the legendary Harley-Davidson Museum in Milwaukee, where you can admire a stunning collection of motorcycles and learn about the brand's history.
$$$, 2 hours

2:00PM

Road Trip to Lake Geneva

Hit the road again for a scenic drive to Lake Geneva, Wisconsin, where you'll spend the rest of the day and evening.
Gas money, 1.5 hours

4:00PM

Relax by the Lake

Unwind and relax by the picturesque shores of Lake Geneva. You can opt for activities like paddleboarding, kayaking, or simply soaking up the serene views.
$-$$, 2 hours

7:00PM

Dinner at Oakfire

Indulge in a delectable wood-fired pizza dinner at Oakfire, known for its cozy ambiance and mouthwatering pizzas.
$$, 1.5 hours
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Day 3: Scenic Morning and Return to Chicago

Lake Geneva, WI, USA

10:00AM

Brunch at Egg Harbor Cafe

Enjoy a leisurely brunch at Egg Harbor Cafe, offering a delightful array of breakfast and brunch options to kickstart your day.
$$, 1 hour

12:00PM

Lake Geneva Canopy Tours

For an adrenaline-pumping experience, partake in the Lake Geneva Canopy Tours, featuring thrilling ziplines and scenic adventures amidst the treetops.
$$$, 2 hours

3:00PM

Drive back to Chicago

Bid farewell to the scenic beauty of Lake Geneva as you embark on the road trip back to Chicago, reminiscing the unforgettable bachelor party adventure.
Gas money, 1.5 hours

6:00PM

Dinner at Bavette's Bar & Boeuf

Conclude the epic bachelor party road trip with a lavish dinner at Bavette's, an upscale steakhouse in Chicago, to celebrate the unforgettable memories made during the trip.
$$$, 2 hours
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Itinerary created by AI-assisted, human-reviewed