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Ultimate Chicago Architecture and Culinary Experience

Ultimate Chicago Architecture and Culinary Experience Itinerary

Last updated: 2024 Jun 14

Architectural Marvels and Deep Dish Delights

Morning
Start your day with a classic Chicago experience at Lou Malnati's Pizzeria, known for its deep-dish pizza. After breakfast, head to the iconic The Magnificent Mile for some leisurely shopping and to admire the city's skyline.
Afternoon
For lunch, indulge in another Chicago favorite at Portillo's Hot Dogs. Afterward, take the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's renowned architecture.
Evening
In the evening, enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city. End the night with a leisurely walk along the Chicago Riverwalk.
Bedtime
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Visit The Magnificent Mile in Chicago
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The Magnificent Mile

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Chicago Architecture Center Cruise on Chicago's First Lady

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Cultural Immersion and Gourmet Exploration

Morning
Enjoy a delightful brunch at The Purple Pig, known for its Mediterranean-inspired cuisine. Afterward, visit the Art Institute of Chicago to explore its world-class art collection.
Afternoon
For a unique experience, have a late lunch at Alinea, a three-Michelin-starred restaurant offering innovative cuisine. Afterward, take a walk in Millennium Park and see the famous Cloud Gate sculpture.
Evening
Conclude your culinary journey with dinner at Girl & The Goat, a top-rated restaurant serving bold flavors. After dinner, take a leisurely evening stroll in the vibrant neighborhood of The Loop.
Bedtime
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Art Institute of Chicago

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Millennium Park

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Skyline Views and Gastro Pub Delights

Morning
Start your day with a hearty breakfast at Au Cheval, known for its indulgent dishes. After breakfast, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.
Afternoon
For lunch, savor the famous burgers at Kuma's Corner, a rock music-themed gastro pub. Afterward, take a walk in the charming neighborhood of Lincoln Park and visit the zoo if you're interested.
Evening
Enjoy a casual dinner at Big Star, known for its tacos and whiskey selection. After dinner, take a relaxing evening cruise on the Chicago Lake Michigan Skyline Cruise.
Bedtime
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Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago
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360 Chicago Observation Deck (Formerly John Hancock Observatory)

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Lincoln Park

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Museum Exploration and Culinary Diversity

Morning
Have a cultural start to your day with breakfast at Xoco, offering a taste of Mexican cuisine. Afterward, visit the Field Museum to explore natural history and anthropology.
Afternoon
For lunch, experience the vibrant flavors of Latin cuisine at Frontera Grill, a renowned restaurant by Chef Rick Bayless. After lunch, continue your museum visits with the Museum of Science and Industry, a must-see in Chicago.
Evening
Conclude your day with a dinner at The Publican, known for its eclectic menu and extensive beer selection. After dinner, take a leisurely walk along the Chicago Riverwalk to enjoy the city lights.
Bedtime
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Visit Field Museum in Chicago
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Field Museum

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Museum of Science and Industry

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