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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 delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a stroll along the Chicago Riverwalk to admire the city's architecture.
Afternoon
For the afternoon, visit the Art Institute of Chicago with a fast-pass ticket to explore its world-class art collection. Afterward, enjoy a late lunch at Giordano's for their famous deep-dish pizza.
Evening
In the evening, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a "Sip and View" ticket to enjoy panoramic views of the city at sunset. Conclude the day with a fine dining experience at Alinea, a three-Michelin-star restaurant.
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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Museum Day and Navy Pier Excursion
Morning
Enjoy a leisurely breakfast at Lula Cafe, a cozy spot known for its farm-to-table fare. Then, spend the morning at the Field Museum of Natural History or opt for a VIP tour for a more in-depth experience.
Afternoon
For lunch, savor the flavors of Mexico at Rick Bayless' Frontera Grill. Afterward, take a relaxing cruise on the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's famous buildings.
4.56Field Museum
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4.56Field Museum
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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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Gangsters, Ghosts, and Culinary Delights
Morning
Start your day with a gourmet brunch on a Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise, enjoying the stunning views of the city from the water.
Afternoon
Embark on the Chicago Discover the Gangsters & Ghosts of the City's Past tour to learn about the city's dark history. For a late lunch, indulge in a Chicago-style hot dog at Portillo's Hot Dogs.
Evening
Enjoy a unique dining experience at The Publican, known for its communal atmosphere and extensive beer selection. After dinner, take a stroll through the city and admire the evening lights.
Bedtime
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4.34Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
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4.34Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
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4.68Chicago Discover the Gangsters & Ghosts of the City's Past
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4.68Chicago Discover the Gangsters & Ghosts of the City's Past
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Science, Architecture, and a Helicopter Tour
Morning
Have a hearty breakfast at Wildberry Pancakes and Cafe, famous for its variety of pancakes. Then, visit the Museum of Science and Industry, immersing yourself in interactive exhibits.
Afternoon
Experience the city from a different perspective with a Private Helicopter Tour of Chicago Skyline. Afterward, enjoy a late lunch at Xoco, a popular spot for Mexican street food.
Evening
Spend the evening at the Willis Tower Skydeck and The Ledge, taking in the breathtaking views of the city. Conclude the day with a dinner at Girl & the Goat, a top-rated restaurant known for its creative dishes.
Bedtime
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.50Private Helicopter Tour of Chicago Skyline
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4.50Private Helicopter Tour of Chicago Skyline
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Final Taste of Chicago and Departure
Morning
For your last morning in Chicago, enjoy a classic Chicago-style breakfast at Lou Mitchell's, a historic diner. Take a leisurely walk through Millennium Park and see the famous "Bean."
Afternoon
Have a farewell lunch at The Signature Room at the 95th, where you can enjoy stunning views of the city. Afterward, do some last-minute shopping on The Magnificent Mile.
4.69Millennium Park
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4.69Millennium Park
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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