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Ultimate Chicago Experience: Architecture, Cuisine, and Culture

Ultimate Chicago Experience: Architecture, Cuisine, and Culture Itinerary

Last updated: 2024 Jun 14

Architectural Marvels and Skyline Views

Morning
Start your day with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's iconic buildings from a unique perspective.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago with a fast-pass ticket to explore its world-class art collection.
Evening
In the evening, enjoy a romantic dinner at The Signature Room at the 95th, offering stunning views of the city. Conclude the day with a Chicago River Guided Sunset Cocktail & Architecture Tour for a magical experience.
Bedtime
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Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago
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Chicago River 1.5-Hour Guided Architecture Cruise

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Art Institute of Chicago

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Culinary Delights and Cultural Immersion

Morning
Indulge in a delicious breakfast at Au Cheval, known for its upscale diner fare. Afterward, take a Chicago Architecture Center Cruise on Chicago's First Lady for more insights into the city's architecture.
Afternoon
For lunch, experience the vibrant atmosphere of Xoco by Rick Bayless, offering gourmet Mexican cuisine. Spend the afternoon exploring the Museum of Science and Industry, a fascinating museum for all ages.
Evening
Enjoy a unique dining experience at Alinea, a three-Michelin-star restaurant. After dinner, take a leisurely walk along the Chicago Riverwalk to soak in the city's ambiance.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Architecture Center Cruise on Chicago's First Lady in Chicago
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Chicago Architecture Center Cruise on Chicago's First Lady

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Visit Museum of Science and Industry in Chicago
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Museum of Science and Industry

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Iconic Landmarks and Local Favorites

Morning
Start your day with a classic Chicago breakfast at Lula Cafe, known for its farm-to-table dishes. Then, visit the Willis Tower Skydeck and The Ledge for panoramic views of the city.
Afternoon
For lunch, enjoy a casual meal at Portillo's Hot Dogs, a Chicago institution. Spend the afternoon exploring the Navy Pier and taking a Chicago Lake Michigan Skyline Cruise.
Evening
Conclude your trip with a dinner at Girl & the Goat, a popular spot for creative cuisine. Afterward, take a stroll down The Magnificent Mile for some last-minute shopping and city views.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Willis Tower Skydeck and The Ledge Ticket in Chicago
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Willis Tower Skydeck and The Ledge

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Visit Navy Pier in Chicago
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Navy Pier

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