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3-day trip to Downtown Chicago Itinerary
Last updated: 2024 Jun 14Exploring the City's Landmarks
Morning
Start your day with a delicious breakfast at Little Goat Diner, known for its creative twists on classic dishes. Afterward, head to Millennium Park to admire the famous Cloud Gate, also known as "The Bean." Take a leisurely stroll along the Chicago Riverwalk and enjoy the scenic views of the city's architecture.
Afternoon
For lunch, indulge in a Chicago-style hot dog at Portillo's Hot Dogs. Afterward, take a guided architecture cruise along the Chicago River with Chicago River 1.5-Hour Guided Architecture Cruise. Learn about the city's iconic buildings and their history.
Evening
Enjoy a delicious dinner at The Purple Pig, known for its Mediterranean-inspired cuisine. Afterward, take a walk along The Magnificent Mile, a famous shopping district, and soak in the vibrant atmosphere of the city at night.
Bedtime
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4.69Cloud Gate
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4.69Cloud Gate
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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Museums and Skydeck
Morning
Start your day with a hearty brunch at Lula Cafe, known for its farm-to-table dishes. Afterward, visit the Art Institute of Chicago and explore its impressive collection of artworks. Don't miss the iconic Chicago Picasso sculpture located nearby.
Afternoon
For lunch, head to Giordano's and savor a deep-dish pizza, a Chicago specialty. Afterward, visit the Field Museum and immerse yourself in natural history and cultural exhibits.
Evening
Experience breathtaking views of the city from the 360 Chicago Observation Deck with a skip-the-line ticket. Enjoy a cocktail while taking in the panoramic views. For dinner, indulge in a steak at Gibsons Bar & Steakhouse, a classic Chicago institution.
Bedtime
Find amazing hotels in Downtown Chicago.
4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.64Chicago Picasso
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4.64Chicago Picasso
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Navy Pier and River Cruise
Morning
Start your day with a delicious breakfast at Au Cheval, known for its mouthwatering burgers and indulgent brunch options. Afterward, visit Navy Pier and take a ride on the Centennial Wheel for stunning views of Lake Michigan.
Afternoon
Enjoy a leisurely lunch at Eataly Chicago, a vibrant Italian marketplace offering a variety of dining options. Afterward, take a family-friendly architecture cruise along the Chicago River with Chicago 45-Minute Family-Friendly Architecture River Cruise.
Evening
For dinner, experience the innovative and multi-sensory tasting menu at Alinea, a world-renowned restaurant. End your evening with a guided sunset cocktail and architecture tour on the Chicago River with Chicago River Guided Sunset Cocktail & Architecture Tour.
Bedtime
Find amazing hotels in Downtown Chicago.
4.48Navy Pier
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4.48Navy Pier
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4.43Centennial Wheel
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4.43Centennial Wheel
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