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Ultimate Chicago Experience in 3 Days Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and Skyline Views

Morning

Start your day with a delightful brunch at Lula Cafe, known for its cozy atmosphere and farm-to-table dishes. Afterward, take a leisurely walk along the Chicago Riverwalk to soak in the city's architecture.

Afternoon

For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Post that, head to the Art Institute of Chicago with a fast-pass ticket to admire world-class art collections.

Evening

In the evening, enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city. Conclude your day with a visit to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a skip-the-line ticket.

Bedtime

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Chicago Riverwalk
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Art Institute of Chicago
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Culinary Delights and Cultural Immersion

Morning

Indulge in a gourmet breakfast at Alinea, a three-Michelin-star restaurant known for its innovative cuisine. After breakfast, take a Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's famous buildings.

Afternoon

For lunch, experience the vibrant atmosphere and Mexican cuisine at Big Star. Afterward, visit the Field Museum of Natural History or opt for a VIP tour for a more in-depth experience.

Evening

Enjoy a unique dining experience at Au Cheval, famous for its burgers. After dinner, immerse yourself in the world of improv comedy at The Second City, a renowned comedy club.

Bedtime

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4.77
Chicago River 1.5-Hour Guided Architecture Cruise
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4.68
Field Museum of Natural History
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Gangsters, Ghosts, and City Views

Morning

Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes. After breakfast, embark on the Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's dark history.

Afternoon

For lunch, enjoy a casual meal at Pequod's Pizza, famous for its caramelized crust. Spend the afternoon exploring the Chicago Cultural Center and the Millennium Park, home to the iconic Cloud Gate sculpture.

Evening

Conclude your trip with a sunset cocktail and architecture tour on the Chicago River Guided Sunset Cocktail & Architecture Tour. After the tour, have a farewell dinner at Girl & The Goat, a popular restaurant serving creative dishes.

Bedtime

Find amazing hotels in Chicago, Illinois.