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Ultimate 3-Day Chicago Exploration with Iconic Sights and Culinary Delights

Ultimate 3-Day Chicago Exploration with Iconic Sights and Culinary Delights Itinerary

Last updated: 2024 Jun 14

City Icons and Sky-High Views

Morning
Start your day with a delightful brunch at Lula Cafe, known for its farm-to-table dishes. Afterward, head to the iconic Cloud Gate, also known as "The Bean," in Millennium Park. Take some time to explore the park and visit the nearby Millennium Park.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Afterward, experience the city from the sky at the 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy a drink with a view using your 360 Chicago Observation Deck Sip and View Ticket.
Evening
In the evening, take a leisurely walk along the Chicago Riverwalk and enjoy dinner at The Purple Pig, known for its Mediterranean-inspired cuisine. End the night with a visit to the The Magnificent Mile for some evening shopping or simply enjoy the vibrant atmosphere.
Bedtime
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Art, Architecture, and River Cruise

Morning
Enjoy a delicious breakfast at Little Goat Diner, a popular spot for creative comfort food. After breakfast, immerse yourself in the world of art at the Art Institute of Chicago. Spend a few hours exploring the impressive collection.
Afternoon
For lunch, head to The Publican and indulge in their farm-to-table fare. Afterward, take a Chicago Architecture Center Cruise on Chicago's First Lady to learn more about the city's architecture and enjoy the views from the river.
Evening
In the evening, experience the city's skyline from the water on a Chicago River Guided Sunset Cocktail & Architecture Tour. Enjoy the sights with a drink in hand. For dinner, try the famous Chicago-style hot dogs at Portillo's Hot Dogs.
Bedtime
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Navy Pier, Lakefront, and Culinary Delights

Morning
Start your day with a scenic walk or bike ride along the Lakefront Trail. For brunch, enjoy a meal at Au Cheval, known for its delicious burgers and upscale diner fare.
Afternoon
Spend the afternoon at Navy Pier, where you can take a ride on the Centennial Wheel and explore the various attractions. For a late lunch, head to Big Star for their renowned tacos.
Evening
Conclude your Chicago adventure with a memorable dinner at Alinea, a three-Michelin-star restaurant known for its innovative and artistic cuisine. After dinner, take a final stroll along the Chicago Riverwalk to soak in the city's vibrant nightlife.
Bedtime
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