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Iconic Chicago: Architecture, Culinary Delights, and Artistry

Iconic Chicago: Architecture, Culinary Delights, and Artistry Itinerary

Last updated: 2024 Jun 14

Architectural Marvels and Skyline Views

Morning
Start your day with a delightful brunch at the renowned The Purple Pig, known for its innovative dishes. Afterward, head to the iconic Millennium Park to see the famous "Bean" and enjoy the serene surroundings.
Afternoon
For lunch, savor the flavors of Chicago at Giordano's, a must-visit for its deep-dish pizza. Post that, take a Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's skyline and learn about its architectural history.
Evening
In the evening, experience the city from above at the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Afterward, enjoy a sophisticated dinner at Alinea, a three-Michelin-starred restaurant known for its avant-garde cuisine.
Bedtime
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Cultural Immersion and Culinary Delights

Morning
Enjoy a leisurely breakfast at Au Cheval, famous for its decadent dishes. Then, immerse yourself in art at the Art Institute of Chicago, home to a world-class collection.
Afternoon
For lunch, head to Girl & The Goat, a top-rated restaurant offering a creative menu. Afterward, take a walk down the historic The Magnificent Mile and do some shopping.
Evening
In the evening, opt for a unique dining experience at Alinea, known for its innovative and theatrical dishes. After dinner, take a leisurely stroll along the Chicago Riverwalk.
Bedtime
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City Exploration and Culinary Delights

Morning
Start your day with a hearty breakfast at Lou Malnati's Pizzeria, a Chicago institution famous for its deep-dish pizza. Then, embark on a Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's history.
Afternoon
For lunch, enjoy the vibrant atmosphere and Mexican cuisine at Big Star. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.
Evening
Indulge in a fine dining experience at Alinea, one of the best restaurants in the world. After dinner, take a relaxing Chicago River Guided Sunset Cocktail & Architecture Tour.
Bedtime
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Museum Day and Culinary Delights

Morning
Begin your day with a delicious breakfast at The Publican, known for its farm-to-table cuisine. Then, explore the Field Museum of Natural History and the Shedd Aquarium.
Afternoon
For lunch, enjoy the seafood at Gibsons Bar & Steakhouse, a classic Chicago eatery. Afterward, visit the Adler Planetarium and take a Chicago Architecture Center Cruise on Chicago's First Lady.
Evening
Conclude your day with a memorable dinner at Alinea, where you can experience culinary artistry at its finest.
Bedtime
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Final Day of Exploration and Departure

Morning
Enjoy a leisurely breakfast at Au Cheval before visiting the Willis Tower Skydeck and The Ledge to take in the city's skyline. Spend some time at Navy Pier before heading to the airport for your departure.
Afternoon
Evening

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