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Exploring Chicago in 3 Days
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Exploring Chicago in 3 Days
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Day 1: The Loop
Chicago, USA
8:00AM
Breakfast at Wildberry Pancakes and Cafe
Start your day with a delicious breakfast at Wildberry Pancakes and Cafe, known for their signature pancakes and creative omelets.
$$, 1 hour
9:30AM
Art Institute of Chicago
Spend the morning exploring the world-renowned Art Institute of Chicago, home to an impressive collection of art from around the globe.
$25, 2-3 hours
12:30PM
Lunch at Lou Malnati's Pizzeria
Indulge in Chicago's famous deep-dish pizza for lunch at Lou Malnati's Pizzeria, a local favorite.
$$, 1 hour
2:30PM
The Field Museum
Explore The Field Museum to learn about natural history, ancient cultures, and the wonders of the world, including the famous T-Rex named Sue.
$28, 2-3 hours
5:30PM
Dinner at The Gage
Enjoy dinner at The Gage, a gastropub offering a mix of rustic and contemporary dishes, located near Millennium Park.
$$, 1.5 hours
Find Hotels in Chicago
Day 2: Magnificent Mile and Navy Pier
Chicago, USA
8:30AM
Breakfast at Beatrix
Start your day with a wholesome breakfast at Beatrix, known for its healthy and flavorful dishes.
$$, 1 hour
10:00AM
Shopping on the Magnificent Mile
Spend the morning shopping along the Magnificent Mile, home to a wide array of luxury boutiques, department stores, and unique shops.
$$-$$$$, 2-3 hours
1:00PM
Lunch at Riva Crab House on Navy Pier
Enjoy a seafood lunch with stunning views of Lake Michigan at Riva Crab House on Navy Pier.
$$$, 1 hour
3:00PM
Explore Navy Pier
Spend the afternoon exploring Navy Pier, where you can visit the Chicago Children's Museum, take a ride on the Centennial Wheel, or simply enjoy the lakefront views.
$-$$$, 2-3 hours
6:00PM
Dinner at The Signature Room at the 95th
Indulge in a sophisticated dinner with panoramic views of the city at The Signature Room, located on the 95th floor of the John Hancock Center.
$$$, 2 hours
Find Hotels in Chicago
Day 3: Lincoln Park and Wicker Park
Chicago, USA
9:00AM
Breakfast at Batter & Berries
Start your day with a delightful breakfast at Batter & Berries, known for its creative and flavorful brunch options.
$$, 1 hour
10:30AM
Lincoln Park Zoo
Spend the morning exploring the Lincoln Park Zoo, one of the oldest zoos in the US, home to a wide variety of animals and beautiful gardens.
Free, 2-3 hours
1:00PM
Lunch at Big Star
Enjoy a casual and lively lunch at Big Star, a popular taco and whiskey spot in Wicker Park.
$$, 1 hour
3:00PM
Wicker Park Boutiques and Cafes
Spend the afternoon wandering through the unique boutiques and trendy cafes in Wicker Park, known for its vibrant arts and music scene.
$-$$$, 2-3 hours
6:00PM
Dinner at The Violet Hour
Experience an intimate speakeasy-style dinner at The Violet Hour, where expert mixologists craft innovative cocktails in a sophisticated setting.
$$$, 2 hours
Find Hotels in Chicago
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Itinerary created by
Plantrip Team
January 26, 2024
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