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Exploring Chicago in 2 Days
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Exploring Chicago in 2 Days
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Day 1: City Landmarks
Chicago, USA on June 7, 2024
9:00AM
Breakfast at Yolk
Start your day with a delicious breakfast at Yolk, known for its creative egg dishes and pancakes.
Yolk is a short walk from Millennium Park.
$15, 1 hour
10:30AM
Millennium Park
Visit the famous Cloud Gate sculpture, also known as 'The Bean', and enjoy the serene Lurie Garden.
Walk to Millennium Park from Yolk.
Free, 2 hours
1:00PM
Lunch at The Gage
Experience upscale American cuisine at The Gage, located near Millennium Park.
The Gage is a short walk from Millennium Park.
$30, 1.5 hours
3:00PM
Art Institute of Chicago
Explore one of the oldest and largest art museums in the United States, home to famous works like Grant Wood's 'American Gothic'.
Walk to the Art Institute of Chicago from The Gage.
$25, 3 hours
6:30PM
Dinner at Riva Crabhouse
Indulge in fresh seafood while enjoying stunning views of Lake Michigan at Riva Crabhouse on Navy Pier.
Take a taxi or public transportation to Navy Pier.
$50, 2 hours
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Day 2: Skyline Views and Shopping
Chicago, USA on June 8, 2024
9:00AM
Breakfast at Wildberry Pancakes and Cafe
Start your day with a scrumptious breakfast at Wildberry Pancakes and Cafe, known for its delicious variety of pancakes.
Wildberry Pancakes and Cafe is near Millennium Park.
$20, 1 hour
10:30AM
Willis Tower Skydeck
Head to the iconic Willis Tower and step out on The Ledge for breathtaking views of the city from 1,353 feet above ground.
Take a short walk to Willis Tower from Wildberry.
$30, 2 hours
1:00PM
Lunch at Giordano's
Try Chicago's famous deep-dish pizza at Giordano's, a beloved spot for locals and tourists alike.
Giordano's is located near Willis Tower.
$25, 1.5 hours
3:00PM
The Magnificent Mile
Shop along the upscale Magnificent Mile, known for its luxury boutiques, department stores, and iconic landmarks.
Take a taxi or public transportation to The Magnificent Mile.
Variable based on shopping, 2 hours
6:00PM
Chicago Riverwalk
Stroll along the beautiful Chicago Riverwalk, lined with restaurants, cafes, and stunning architecture.
Walk or take a boat tour from The Magnificent Mile to Riverwalk.
Free, 2 hours
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Itinerary created by
Plantrip Team
May 29, 2024
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