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3-Day Chicago City Adventure Itinerary Itinerary
Last updated: 2024 Jun 14Architectural Marvels and River Cruises
Morning
Begin your Chicago adventure with a delightful breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. Afterward, take a stroll along the iconic Chicago Riverwalk to admire the city's architecture and make your way to the Chicago River 1.5-Hour Guided Architecture Cruise for a comprehensive tour of the stunning skyscrapers.
Afternoon
Evening
As the sun sets, dine at The Signature Room at the 95th and enjoy world-class cuisine with breathtaking views of the Chicago skyline. End your evening with a thrilling experience on the Chicago Willis Tower Skydeck and The Ledge, stepping out onto the glass-floored balconies for heart-pounding views.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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Museums and Cultural Wonders
Morning
Start your day with a hearty breakfast at Au Cheval, famous for its mouthwatering burgers. Then, immerse yourself in the natural world at the Shedd Aquarium, where you can witness a stunning variety of marine life from around the globe.
Afternoon
After the aquarium, enjoy a leisurely lunch at The Purple Pig, known for its innovative, Mediterranean-inspired dishes. Spend your afternoon exploring the fascinating exhibits of the Field Museum, including the celebrated Sue the T. rex.
Evening
For dinner, head to Girl & the Goat and indulge in a menu of bold flavors and local ingredients. Cap off your day with a visit to the Chicago Theatre for a memorable live performance in one of the city's most iconic venues.
Bedtime
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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4.56Field Museum
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4.56Field Museum
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City Sights and Skyline Views
Morning
Enjoy a delightful breakfast at Lula Cafe, a neighborhood favorite known for its seasonal, locally-sourced menu. Then, take a morning stroll through the lush landscapes of Millennium Park, where you can't miss the famous "Bean" sculpture, officially known as Cloud Gate.
Afternoon
For lunch, visit Eataly Chicago, a vibrant Italian marketplace with a variety of dining options. Spend your afternoon exploring the shops and cultural landmarks of The Magnificent Mile, Chicago's premier shopping destination.
Evening
Dine at RPM Italian, where modern Italian cuisine meets a stylish atmosphere. Conclude your Chicago adventure with a visit to the 360 Chicago Observation Deck, formerly known as the John Hancock Observatory, and enjoy a drink with a view as you reflect on your time in the Windy City.
Bedtime
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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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