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Chicago Adventure - 5 Days of Excitement

Chicago Adventure - 5 Days of Excitement Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning
Start your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). This iconic skyscraper offers breathtaking views of the city from its observation deck. It's a great way to get an overview of Chicago's layout and major landmarks.
Afternoon
Head over to Millennium Park for a leisurely stroll. Don't miss the famous Cloud Gate sculpture, also known as 'The Bean.' For lunch, enjoy some deep-dish pizza at Lou Malnati's Pizzeria.
Evening
In the evening, catch a live performance at House of Blues. This legendary venue offers a fantastic atmosphere and great music. For dinner, dine at Girl & the Goat, known for its innovative dishes.
Bedtime
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Skydeck Chicago at Willis Tower (Sears Tower)

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Exploring Chicago's Cultural Gems

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 regions.
Afternoon
After exploring the museum, take a walk along Chicago Riverwalk. It's a beautiful place to relax and enjoy views of the river. Have lunch at The Purple Pig, which offers delicious Mediterranean-inspired dishes.
Evening
Spend your evening at Navy Pier, where you can enjoy rides, games, and stunning views of Lake Michigan. For dinner, savor some classic American fare at Joe's Seafood, Prime Steak & Stone Crab.
Bedtime
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Chicago Riverwalk

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Architectural Wonders and Local Flavors

Morning
Kick off your day with an architectural tour starting with Rookery Building, one of Chicago's most historically significant buildings.
Afternoon
Next up is a visit to the famous Wrigley Field, home of the Chicago Cubs. Even if you're not catching a game, it's worth seeing this historic ballpark. Grab lunch nearby at Portillo's Hot Dogs for some iconic Chicago-style hot dogs.
Evening
In the evening, explore more architectural marvels like Marina City and then head over to dine at Alinea, one of Chicago’s most celebrated restaurants offering an unforgettable dining experience.
Bedtime
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Science and Serenity in Chicago

Morning
Start your morning with a visit to the fascinating Museum of Science and Industry. This museum offers interactive exhibits that are fun for all ages.
Afternoon
Afterward, unwind with a peaceful walk through Grant Park, often referred to as 'Chicago’s front yard.' Have lunch at nearby Frontera Grill, known for its delicious Mexican cuisine.
Evening
Conclude your day by visiting the iconic Chicago Theatre for an evening show. For dinner afterward, indulge in some hearty BBQ at Smoque BBQ.
Bedtime
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Final Day of Chicago Delights

Morning
Begin your last day in Chicago with a visit to Shedd Aquarium. This world-class aquarium is home to thousands of marine animals and offers engaging exhibits that are perfect for all ages.
Afternoon
After the aquarium, head over to Adler Planetarium which is nearby. The planetarium offers fascinating exhibits about space and astronomy. For lunch, enjoy a meal at Gibsons Bar & Steakhouse, known for its prime steaks and classic American fare.
Evening
Spend your final evening in Chicago at 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of the city as the sun sets. For dinner, treat yourself to a meal at Au Cheval, famous for its burgers and upscale diner atmosphere.
Bedtime
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Adler Planetarium

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