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Ultimate Chicago Experience: Architecture, Cuisine, and Culture Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Skyline Views
Morning
Start your day with a delicious brunch at The Purple Pig, known for its Mediterranean-inspired cuisine. Afterward, take a stroll to Millennium Park to see the famous "Bean" and enjoy the outdoor art.
Afternoon
For lunch, savor the deep-dish pizza at Lou Malnati's Pizzeria. Then, visit the Art Institute of Chicago to admire its world-class art collection.
Evening
In the evening, have a memorable dining experience at Alinea, a three-Michelin-star restaurant. After dinner, take a leisurely walk along the Chicago Riverwalk to enjoy the city lights.
Bedtime
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Architectural Marvels and River Cruises
Morning
Enjoy a gourmet breakfast at Lula Cafe, a cozy spot with a focus on local ingredients. Then, embark on the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's iconic buildings.
Afternoon
For lunch, head to Xoco for a taste of authentic Mexican cuisine. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning views of the city.
Evening
Dine at Girl & the Goat, a popular restaurant with a creative menu. End your day with a Chicago River Guided Sunset Cocktail & Architecture Tour.
Bedtime
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Museum Day and Navy Pier Adventure
Morning
Start your day with a hearty breakfast at Little Goat Diner, known for its comfort food. Then, visit the Field Museum to explore natural history and cultural exhibits.
Afternoon
Have a leisurely lunch at Giordano's for their famous stuffed deep-dish pizza. Afterward, spend the afternoon at Navy Pier and take a ride on the Navy Pier Centennial Wheel.
Evening
Enjoy a seafood dinner at The Publican, a European beer hall-inspired restaurant. Conclude your day with a Chicago 1.5-Hour Romantic Sunset Cruise on Lake Michigan.
Bedtime
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Culinary Delights and Neighborhood Exploration
Morning
Indulge in a gourmet breakfast at Au Cheval, known for its famous burger. After breakfast, take a Chicago River 1.5-Hour Guided Architecture Riverboat Tour to see the city from a different perspective.
Afternoon
For lunch, experience the vibrant atmosphere of Big Star while enjoying their tacos. Spend the afternoon exploring the trendy neighborhoods of Wicker Park and Bucktown.
Evening
Dine at Girl & the Goat, a top-rated restaurant known for its bold flavors. After dinner, explore the nightlife in the River North area.
Bedtime
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Final Day of Shopping and Farewell to Chicago
Morning
Enjoy a leisurely breakfast at Lula Cafe, a neighborhood favorite. Spend the morning shopping along the The Magnificent Mile, home to a variety of luxury boutiques and department stores.
Afternoon
For your last meal in Chicago, savor the flavors of Italy at RPM Italian. After lunch, take a relaxing walk in the serene surroundings of Lincoln Park.
Evening
Conclude your trip with a classic Chicago experience - a hot dog from Portillo's Hot Dogs. Reflect on your journey as you enjoy this iconic Chicago meal.
Bedtime
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