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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 delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a stroll along the famous Magnificent Mile for some upscale shopping and iconic architecture.
Afternoon
For lunch, savor the deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic. Then, visit the Art Institute of Chicago with your fast-pass ticket to admire a world-class art collection.
Evening
In the evening, head to the 360 Chicago Observation Deck with your skip-the-line ticket for breathtaking views of the city at sunset. Conclude the day with a gourmet dinner cruise on Lake Michigan, enjoying the skyline with Spirit of Chicago.
Bedtime
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Art Institute of Chicago

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Cultural Immersion and River Exploration

Morning
Enjoy a relaxed morning at Millennium Park, home to the famous Cloud Gate sculpture. Have a leisurely brunch at Lula Cafe, known for its farm-to-table cuisine.
Afternoon
Afterward, take the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's renowned architecture. For a late afternoon snack, indulge in churros at Xoco by Rick Bayless.
Evening
For dinner, experience the vibrant atmosphere and small plates at Cafe Ba-Ba-Reeba!. End the day with a Chicago River Guided Sunset Cocktail & Architecture Tour for a unique perspective of the city.
Bedtime
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Millennium Park

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Chicago Architecture Center Cruise

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Museum Day and Culinary Delights

Morning
Begin your day with a hearty breakfast at Au Cheval, famous for its indulgent burgers. Then, explore the Field Museum of Natural History or opt for a VIP tour for a more in-depth experience.
Afternoon
For lunch, enjoy the vibrant flavors of Mexico at Frontera Grill by Rick Bayless. Spend the afternoon at the Museum of Science and Industry, immersing yourself in interactive exhibits.
Evening
Conclude your Chicago adventure with a fine dining experience at Alinea, a three-Michelin-star restaurant. After dinner, take a leisurely walk along the Chicago Riverwalk to savor the city's beauty at night.
Bedtime
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Field Museum of Natural History

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Museum of Science and Industry

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