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Ultimate 3-Day Chicago Experience: Architecture, Cuisine, and Culture

Ultimate 3-Day 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 cuisine. Afterward, take a Chicago Architecture Center Cruise on Chicago's First Lady to immerse yourself in the city's iconic architecture.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago to explore its world-class art collection.
Evening
In the evening, enjoy a sophisticated dinner at Alinea, a three-Michelin-star restaurant. Afterward, take a Chicago River Guided Sunset Cocktail & Architecture Tour for a unique perspective of the city.
Bedtime
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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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Art Institute of Chicago

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Museum Day and Navy Pier Excursion

Morning
Start your day with a delicious breakfast at Lula Cafe, known for its farm-to-table fare. Then, visit the Field Museum of Natural History to delve into the world of natural science.
Afternoon
For lunch, enjoy a variety of options at Eataly Chicago. Afterward, take a leisurely stroll at Navy Pier and consider a ride on the Centennial Wheel for panoramic views.
Evening
Dine at Girl & the Goat, a popular spot for its creative dishes. Conclude your day with a visit to the Chicago Theatre for a show or simply admire its iconic marquee.
Bedtime
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Visit Chicago Field Museum of Natural History Ticket or VIP Tour in Chicago
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Field Museum of Natural History

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Visit Navy Pier in Chicago
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Navy Pier

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Lakefront Adventures and Culinary Delights

Morning
Enjoy a classic Chicago breakfast at Wildberry Pancakes and Cafe. Then, take a Chicago Lake Michigan Skyline Cruise to appreciate the city's skyline from the water.
Afternoon
For lunch, indulge in a gourmet experience on the Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Afterward, visit the 360 Chicago Observation Deck for more stunning views.
Evening
End your Chicago journey with a memorable dinner at Gibsons Bar & Steakhouse, a renowned steakhouse. Afterward, take a walk along the Riverwalk to soak in the city's vibrant atmosphere.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Lake Michigan Skyline Cruise in Chicago
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Chicago Lake Michigan Skyline Cruise

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Visit Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise in Chicago
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Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

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