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Ultimate Chicago Experience: Architecture, Food, and Culture Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Skyline Views
Morning
Start your day with a delicious brunch at Lula Cafe, known for its vibrant atmosphere and farm-to-table dishes. Afterward, take a leisurely walk along the Chicago Riverwalk to admire the city's architecture.
Afternoon
For lunch, indulge in a deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic. Afterward, visit the Art Institute of Chicago to explore its world-class art collection.
Evening
Enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city. End the day with a visit to the The Magnificent Mile for some evening shopping or a leisurely stroll.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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Architectural Marvels and River Cruises
Morning
Have a hearty breakfast at Au Cheval, famous for its indulgent burgers. Then, embark on the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's iconic buildings.
Afternoon
For lunch, savor the flavors of Mexico at Xoco, a restaurant by a renowned chef. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views.
Evening
Dine at The Publican, known for its communal dining experience and extensive beer selection. Take a leisurely walk around Millennium Park and admire the famous "Bean" sculpture.
Bedtime
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4.46Chicago Architecture Center Cruise on Chicago's First Lady
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4.46Chicago Architecture Center Cruise on Chicago's First Lady
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Culinary Delights and Cultural Immersion
Morning
Start your day with a delightful breakfast at Little Goat Diner, a cozy spot with a creative menu. Then, explore the Chicago Cultural Center, known for its stunning architecture and free art exhibitions.
Afternoon
Enjoy a leisurely lunch at Girl & The Goat, a top-rated restaurant with a focus on bold flavors. Afterward, take a guided tour of the Chicago Theatre to learn about its rich history.
Evening
Indulge in a fine dining experience at Alinea, a three-Michelin-star restaurant offering a multi-sensory tasting menu. After dinner, take a stroll along the Chicago River to see the city lights.
Bedtime
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4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.71Chicago Theatre
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4.71Chicago Theatre
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Museum Day and Lake Michigan Cruise
Morning
Enjoy a relaxed breakfast at Longman & Eagle, a hip spot known for its brunch. Then, spend the morning exploring the Field Museum and the Shedd Aquarium.
Afternoon
For lunch, head to Giordano's to try their famous stuffed deep-dish pizza. In the afternoon, take a Chicago Lake Michigan Skyline Cruise to see the city from the water.
Evening
Dine at The Purple Pig, a popular restaurant offering a variety of Mediterranean dishes. Afterward, take a leisurely walk in Grant Park and enjoy the evening breeze.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Final Day of Exploration and Farewell to Chicago
Morning
For your last morning in Chicago, have a classic breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes. Then, visit the Willis Tower Skydeck and The Ledge to get a bird's eye view of the city.
Afternoon
Enjoy a farewell lunch at Gibsons Bar & Steakhouse, a Chicago institution. Spend the rest of the afternoon shopping and exploring the boutiques on The Magnificent Mile.
Evening
Conclude your trip with a memorable dinner at Au Cheval, known for its upscale diner fare. After dinner, take a walk along the Chicago Riverwalk to soak in the vibrant atmosphere of the city.
Bedtime
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4.41Willis Tower Skydeck and The Ledge
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4.41Willis Tower Skydeck and The Ledge
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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