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Labor Day Weekend in Chicago: Iconic Sights and Hidden Gems Itinerary
Last updated: 2024 Jun 14From Route 66 to River Cruises: A Day of Chicago Wonders
Morning
Start your day with a classic breakfast at Lou Mitchell’s, a historic spot in Chicago. Afterward, take a walk to the Route 66 Sign to capture the essence of this iconic highway.
Afternoon
For lunch, head to Pequod's Pizza for their famous deep-dish pizza. Continue your journey to see The Bean in Millennium Park and enjoy the surrounding Grant Park.
Evening
In the evening, experience the vibrant atmosphere of Navy Pier. Enjoy a ride on the Centennial Wheel and savor a delightful dinner at Riva Crabhouse. Conclude the night with a Chicago Riverwalk stroll.
Bedtime
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4.90Route 66 Sign
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4.90Route 66 Sign
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4.61The Bean
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4.61The Bean
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Speakeasies and Sunset Cruises: A Magical Evening Awaits
Morning
Indulge in a delightful breakfast at The Purple Pig, known for its unique dishes. Afterward, take a leisurely walk around the Wrigley Building and the Tribune Tower.
Afternoon
For lunch, enjoy the vibrant atmosphere of Big Star and savor their delicious tacos. Spend the afternoon exploring the Green Mill Cocktail Lounge, a historic jazz club.
Evening
Embark on a magical Chicago River Guided Sunset Cocktail & Architecture Tour and witness the city's skyline transform as the sun sets. After the cruise, immerse yourself in the world of magic at The Magic Lounge. Conclude your trip with a late dinner at The Signature Room at the 95th, offering stunning views of the city.
Bedtime
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4.39Wrigley Building
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4.39Wrigley Building
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4.61Tribune Tower
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4.61Tribune Tower
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