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Weekend Getaway to Chicago

Weekend Getaway to Chicago Itinerary

Last updated: 2024 Jun 14

Exploring Chicago's Iconic Landmarks

Morning
Kick off your Chicago adventure with a hearty breakfast at Eataly Chicago. Start your sightseeing with Skydeck Chicago at Willis Tower (Sears Tower) for a panoramic view of the city. Then, head to The Magnificent Mile for some retail therapy.
Afternoon
For lunch, try the famous deep-dish pizza at Lou Malnati's Pizzeria. Spend your afternoon at Art Institute of Chicago and then take a leisurely stroll along the Chicago Riverwalk.
Evening
Dine at Girl & the Goat for a culinary delight. End your day with a visit to Chicago Theatre for a mesmerizing performance.
Bedtime
Find amazing hotels in Chicago.
Visit Skydeck Chicago at Willis Tower (Sears Tower) in Chicago
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Skydeck Chicago at Willis Tower (Sears Tower)

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Visit The Magnificent Mile in Chicago
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The Magnificent Mile

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Discovering Chicago's Cultural and Natural Beauty

Morning
Start your day with a delicious breakfast at Little Goat Diner. Visit the Field Museum and Shedd Aquarium for a dive into natural history and marine life.
Afternoon
Enjoy a Chicago-style hot dog for lunch at Portillo's Hot Dogs. Spend your afternoon at Lincoln Park & Zoo and Adler Planetarium for some outdoor fun and stargazing.
Evening
Savor dinner at Alinea, one of Chicago's finest restaurants. Finish your day with a breathtaking view of the city at night from 360 Chicago Observation Deck (Formerly John Hancock Observatory).
Bedtime
Find amazing hotels in Chicago.
Visit Field Museum in Chicago
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Field Museum

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Visit Shedd Aquarium in Chicago
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Shedd Aquarium

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