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5 Days in Chicago Illinois Itinerary
Last updated: 2024 Jun 14Exploring Downtown Chicago
Morning
Start your day with a visit to the iconic Millennium Park, home to the famous Cloud Gate sculpture (The Bean). Enjoy a coffee at Eataly Chicago - La Pizza & La Pasta before heading to the next attraction.
Afternoon
Walk over to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. For lunch, savor some deep-dish pizza at Lou Malnati's Pizzeria.
Evening
Stroll along the Chicago Riverwalk and enjoy dinner at The Purple Pig, known for its Mediterranean-inspired small plates.
Bedtime
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Millennium Park
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Art Institute of Chicago
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Chicago Riverwalk
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Cultural and Historical Highlights
Morning
Begin your day with a visit to the historic Chicago Cultural Center. Have breakfast at Au Cheval, famous for its burgers.
Afternoon
Explore the exhibits at the renowned Field Museum. For lunch, try some classic Chicago-style hot dogs at Portillo's Hot Dogs.
Evening
Catch a show at the legendary Chicago Theatre. Dine afterward at Girl & The Goat, offering innovative American dishes.
Bedtime
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Chicago Cultural Center
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Field Museum
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Chicago Theatre
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Architectural Wonders and Shopping
Morning
Visit the impressive Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city. Grab breakfast nearby at The Publican, known for its hearty fare.
Afternoon
Take an architectural boat tour along the Chicago River to learn about Chicago's stunning skyline. Enjoy lunch at Al's Beef, famous for its Italian beef sandwiches.
Evening
Shop along The Magnificent Mile, one of Chicago's most famous shopping districts. End your day with dinner at RPM Steak.
Bedtime
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Skydeck Chicago at Willis Tower (Sears Tower)
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Chicago River
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The Magnificent Mile
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Museums and Lakefront Fun
Morning
Start your day with a visit to the fascinating exhibits at the Museum of Science and Industry. Have breakfast beforehand at a local favorite, Honey Butter Fried Chicken.
Afternoon
Head over to explore marine life at the impressive Shedd Aquarium. For lunch, enjoy some delicious tacos from Big Star Wicker Park.
Evening
Spend your evening enjoying rides and attractions on Navy Pier. Dine nearby on fresh seafood from Joe's Seafood Prime Steak & Stone Crab.
Bedtime
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Museum of Science and Industry
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Shedd Aquarium
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Navy Pier
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Parks and Sports Enthusiasts Day Out
Morning
Take a leisurely stroll through Grant Park and enjoy breakfast in nature from Parson's Chicken & Fish Logan Square before heading out.
Afternoon
Catch an afternoon game or tour of historic Wrigley Field followed by lunch from nearby iconic spot Kuma's Corner - West Loop (original location in Avondale).
Evening
End your trip with dinner reservations at Michelin-starred restaurant Alinea after enjoying some live music performances from House of Blues.
Bedtime
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Grant Park
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Wrigley Field
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House of Blues
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