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5-day Adventure in Chicago: Skyline, Cuisine, and Culture Itinerary
Last updated: 2024 Jun 14Discovering the Heart of Chicago
Morning
Start your day with a delicious breakfast at Little Goat Diner. Then, head to the iconic Skydeck Chicago at Willis Tower (Sears Tower) for an unforgettable view of the city.
Afternoon
Grab a quick lunch at Portillo's Hot Dogs before exploring the Chicago River and the beautiful Chicago Riverwalk.
Evening
Enjoy a gourmet dinner at Alinea, followed by a night stroll along the famous The Magnificent Mile.
Bedtime
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Immersing in Chicago's Art and Culture
Morning
Begin your day with breakfast at Eataly Chicago. Spend your morning at the Art Institute of Chicago and the Chicago Cultural Center.
Afternoon
Evening
Dine at Girl & the Goat and end your day with a show at the Chicago Theatre.
Bedtime
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Exploring Chicago's Parks and Museums
Morning
Afternoon
Enjoy lunch at Frontera Grill and spend your afternoon at the Field Museum and the Museum of Science and Industry.
Evening
Have dinner at Gibsons Bar & Steakhouse and take a leisurely walk in the Grant Park.
Bedtime
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A Day in the Life of a Chicagoan
Morning
Afternoon
Evening
Dine at Au Cheval and end your day with a visit to the historic Palmer House Hilton.
Bedtime
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Unveiling Chicago's Architectural Gems
Morning
Start your day with breakfast at Kuma's Corner. Visit the Rookery Building and the Water Tower Place.
Afternoon
Evening
Have your farewell dinner at Giordano's and end your Chicago adventure with a visit to the Biograph Theater and the Chicago Picasso (The Picasso).
Bedtime
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