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5-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Exploring Downtown Chicago
Morning
Start your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). This iconic observation deck offers breathtaking views of the city and is a great way to get oriented.
Afternoon
Head over to Millennium Park for a leisurely stroll. Don't miss the famous Cloud Gate sculpture (The Bean). For lunch, enjoy a delicious meal at The Purple Pig, known for its Mediterranean-inspired small plates.
Evening
Spend your evening at House of Blues. This legendary music venue offers live performances and a vibrant atmosphere. For dinner, savor some classic American cuisine at Gibsons Bar & Steakhouse.
Bedtime
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Skydeck Chicago at Willis Tower (Sears Tower)
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Millennium Park
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House of Blues
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Cultural and Historical Highlights
Morning
Begin your day with a visit to the Art Institute of Chicago. This world-renowned museum houses an impressive collection of art from various periods and cultures.
Afternoon
Take a walk along the Chicago Riverwalk and enjoy the scenic views. Stop for lunch at Portillo's Hot Dogs to try their famous Chicago-style hot dogs.
Evening
Explore the historic Chicago Theatre in the evening. Afterward, dine at Girl & the Goat, one of Chicago's most celebrated restaurants.
Bedtime
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Art Institute of Chicago
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Chicago Riverwalk
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Chicago Theatre
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Architectural Wonders and Sports Fun
Morning
Visit the iconic Wrigley Building and take in its stunning architecture. Then head over to Marina City, known for its unique design.
Afternoon
Catch an afternoon game or tour at Wrigley Field, home of the Chicago Cubs. For lunch nearby, try some deep-dish pizza at Lou Malnati's Pizzeria.
Evening
Spend your evening exploring Wicker Park. Enjoy dinner at Au Cheval, famous for its burgers.
Bedtime
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Wrigley Building
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Marina City
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Wrigley Field
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Science and Natural Beauty
Morning
Start your day with a visit to the fascinating Museum of Science and Industry. Plan to spend several hours here as there is much to see.
Afternoon
Head over to the beautiful Lincoln Park & Zoo for a relaxing afternoon surrounded by nature. Grab lunch nearby at one of Lincoln Park's charming cafes.
Evening
End your day with a visit to the stunning waterfront area of Navy Pier. Enjoy dinner with lake views at one of Navy Pier's restaurants before taking in some evening entertainment.
Bedtime
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Museum of Science and Industry
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Lincoln Park & Zoo
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Final Day in Chicago
Morning
Start your final day with a visit to Adler Planetarium. This planetarium offers fascinating exhibits and stunning views of the city skyline.
Afternoon
After the planetarium, head to Shedd Aquarium for an underwater adventure. For lunch, enjoy some delicious seafood at Joe's Seafood, Prime Steak & Stone Crab, which is conveniently located nearby.
Evening
Conclude your trip with a relaxing evening at Chicago River. Take a river cruise to see the city from a different perspective. For dinner, savor some mouth-watering BBQ at Smoque BBQ.
Bedtime
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Adler Planetarium
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Shedd Aquarium
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Chicago River
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