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Ultimate Chicago Experience in 3 Days

Ultimate Chicago Experience in 3 Days Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Skyline Views

Morning
Start your day with a delicious brunch at Au Cheval, known for its famous burger. Afterward, take a stroll along the Millennium Park and marvel at the Cloud Gate sculpture, also known as "The Bean."
Afternoon
For lunch, head to Giordano's for a taste of Chicago's famous deep-dish pizza. 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 360 Chicago Observation Deck (Formerly John Hancock Observatory) for a panoramic night view of Chicago.
Bedtime
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Culinary Delights and River Cruises

Morning
Start your day with a delightful breakfast at Lula Cafe, known for its farm-to-table cuisine. After breakfast, take a relaxing Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's iconic buildings.
Afternoon
For lunch, savor the flavors of Mexico at Xoco, a restaurant by award-winning chef Rick Bayless. Afterward, explore the Chicago Riverwalk and enjoy the riverside views.
Evening
Indulge in a unique dining experience at Alinea, a three-Michelin-star restaurant offering innovative and artistic dishes. Conclude your day with a Chicago River Guided Sunset Cocktail & Architecture Tour for a magical evening on the water.
Bedtime
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Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago
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Chicago River 1.5-Hour Guided Architecture Cruise

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Sports, History, and Local Favorites

Morning
Enjoy a classic Chicago breakfast at Lou Malnati's Pizzeria with a taste of their famous deep-dish pizza. After breakfast, visit the Wrigley Field for a guided tour of this historic baseball stadium.
Afternoon
For lunch, head to Portillo's Hot Dogs for a true Chicago hot dog experience. Afterward, immerse yourself in the city's history with a visit to the Field Museum of Natural History.
Evening
Conclude your trip with a casual dinner at Big Star, known for its tacos and whiskey selection. After dinner, take a leisurely walk along the Navy Pier and enjoy the festive atmosphere.
Bedtime
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Wrigley Field

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Field Museum of Natural History

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