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Ultimate 2-Day Chicago Adventure with Iconic Sights and Local Bites

Ultimate 2-Day Chicago Adventure with Iconic Sights and Local Bites Itinerary

Last updated: 2024 Jun 14

Architectural Marvels and Sky-High Thrills

Morning
Begin your Chicago journey with a delightful breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. After fueling up, head to the iconic Chicago River 1.5-Hour Guided Architecture Cruise. Marvel at the city's stunning skyline and learn about its rich architectural history.
Afternoon
For lunch, savor the mouthwatering tacos at Big Star. Post-lunch, enjoy the breathtaking views from the Chicago Willis Tower Skydeck and The Ledge Ticket. Walk out onto the glass-bottom Ledge and feel like you're floating above the city.
Evening
As the sun sets, take a leisurely stroll at the vibrant Navy Pier. Dine at The Signature Room at the 95th and indulge in a sumptuous meal with panoramic views of the city. Wrap up the night with the Chicago 360 Chicago Observation Deck Sip and View Ticket, enjoying drinks and the sparkling city lights.
Bedtime
Find amazing hotels in Chicago.
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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Visit Chicago Willis Tower Skydeck and The Ledge Ticket in Chicago
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Chicago Willis Tower Skydeck and The Ledge Ticket

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Cultural Immersion and Scenic Serenity

Morning
Kick off the day with a hearty breakfast at Au Cheval, famous for its decadent burgers. Afterward, take a stroll through the serene Millennium Park. Don't miss the iconic Cloud Gate sculpture, also known as The Bean.
Afternoon
Enjoy a sophisticated lunch at The Purple Pig, offering a menu of artisanal cheeses and charcuterie. Spend your afternoon exploring the world-class exhibits at the Art Institute of Chicago with a Fast-Pass Ticket.
Evening
For dinner, experience the lively atmosphere and Spanish flavors at Cafe Ba-Ba-Reeba!. Cap off your trip with a relaxing walk along the Chicago Riverwalk, taking in the beautiful views and the vibrant pulse of the city.
Bedtime
Find amazing hotels in Chicago.
Visit Millennium Park in Chicago
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Millennium Park

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Visit Art Institute of Chicago in Chicago
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Art Institute of Chicago

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