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21 Days of Chicago Exploration

21 Days of Chicago Exploration Itinerary

Last updated: 2024 Jun 14

Exploring Chicago's Icons

Morning
Start your day with a visit to the iconic The Magnificent Mile for some shopping and sightseeing. Then, head to the historic Chicago Cultural Center for a cultural experience.
Afternoon
Enjoy a delicious lunch at The Purple Pig known for its unique dishes. After lunch, explore the stunning architecture of Rookery Building and take a stroll along the scenic Chicago Riverwalk.
Evening
Indulge in a fine dining experience at Alinea for dinner, known for its innovative cuisine. End your evening with live jazz music at House of Blues.
Bedtime
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Museum Day in Chicago

Morning
Visit the world-renowned Art Institute of Chicago to explore its impressive art collection. Afterward, have brunch at Lula Cafe known for its cozy atmosphere and delicious food.
Afternoon
Spend your afternoon at the fascinating Field Museum to learn about natural history. Then, take a leisurely walk in Grant Park to enjoy the greenery and views.
Evening
Dine at Girl & the Goat for a delightful dinner experience. After dinner, head to a local jazz club like Second City for some live music.
Bedtime
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Art Institute of Chicago

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Architectural Marvels & Local Eats

Morning
Explore the architectural wonders of Chicago by visiting landmarks like Wrigley Building and taking a tour of the historic Chicago Board of Trade Building. Grab breakfast at Wildberry Pancakes and Cafe known for its delicious pancakes.
Afternoon
Discover more architectural gems like Marina City and enjoy lunch at Big Star - Wicker Park for some local flavors. Take a relaxing walk along the beautiful Lake Michigan shoreline.
Evening
For dinner, savor deep-dish pizza at Lou Malnati's Pizzeria. End your evening with drinks at a local bar like Gibsons Bar & Steakhouse.
Bedtime
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Wrigley Building

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Chicago Board of Trade Building

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Parks & Cultural Delights

Morning
Start your day with a visit to the picturesque Lincoln Park & Zoo. Enjoy breakfast at{ R-Xoco}, known for its Mexican cuisine with a modern twist.
Afternoon
Explore the green oasis of{ A-Millennium Park [1212]}, home to famous attractions like Cloud Gate (The Bean). Have lunch at{ R-Cafe Ba-Ba-Reeba!}, offering delicious Spanish tapas.
Evening
Dine at{ R-Frontera Grill} for authentic Mexican flavors. In the evening, take part in cultural activities like visiting{ A-Chicago Theatre [17713]} or enjoying an evening show.
Bedtime
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