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5-day Exciting Exploration of Chicago

5-day Exciting Exploration of Chicago Itinerary

Last updated: 2024 Jun 14

Downtown Chicago and Sky-High Views

Morning
Start your day with a hearty breakfast at Lou Malnati's Pizzeria. Then, head to Skydeck Chicago at Willis Tower (Sears Tower) for a breathtaking view of the city.
Afternoon
Grab a quick lunch at The Purple Pig before exploring The Magnificent Mile for a shopping spree. Don't miss the iconic Wrigley Building and Tribune Tower.
Evening
Enjoy a fine dining experience at Alinea, one of Chicago's top-rated restaurants. End your day with a leisurely stroll along the Chicago Riverwalk.
Bedtime
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Skydeck Chicago at Willis Tower (Sears Tower)

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The Magnificent Mile

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Wrigley Building

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Tribune Tower

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Chicago Riverwalk

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Parks and Museums Galore

Morning
Kick off your day with breakfast at Eataly Chicago. Spend your morning exploring the beautiful Millennium Park and Grant Park.
Afternoon
Have lunch at Girl & the Goat before immersing yourself in art at the Art Institute of Chicago.
Evening
Dine at Au Cheval and then head to the Chicago Theatre for a captivating performance.
Bedtime
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Millennium Park

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Grant Park

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Art Institute of Chicago

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Chicago Theatre

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Exploring Chicago's Waterfront

Morning
Start your day with breakfast at Little Goat Diner. Then, visit the Navy Pier for a fun-filled morning.
Afternoon
Grab lunch at Portillo's Hot Dogs and then explore the Adler Planetarium and Shedd Aquarium.
Evening
Enjoy dinner at Gibsons Bar & Steakhouse and then take a relaxing walk along the Chicago River.
Bedtime
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Navy Pier

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Adler Planetarium

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Shedd Aquarium

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Chicago River

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Historic Landmarks and Sports

Morning
Have breakfast at Frontera Grill and then visit the historic Wrigley Field.
Afternoon
Grab lunch at Giordano's and then explore the United Center and Soldier Field.
Evening
Dine at Big Star and then enjoy a nightcap at Revolution Brewing.
Bedtime
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Wrigley Field

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United Center

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Soldier Field

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Cultural Experiences and Iconic Architecture

Morning
Start your day with breakfast at Kuma's Corner. Then, visit the Chicago Cultural Center and Palmer House Hilton.
Afternoon
Have lunch at Smoque BBQ and then explore the Rookery Building and Frederick C. Robie House.
Evening
Enjoy your final dinner in Chicago at Longman & Eagle and then take a final stroll through the Chicago Loop.
Bedtime
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Chicago Cultural Center

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Palmer House Hilton

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Rookery Building

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Frederick C. Robie House

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Chicago Loop

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Adjacent Cities

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