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Roam Around

4 Days in Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic landmarks. Here you can see the famous Cloud Gate sculpture (often referred to as 'The Bean') and enjoy the beautiful gardens and public art installations.

Afternoon

Head over to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its vast collection of artworks from around the world.

Evening

Dine at Alinea, a renowned restaurant known for its innovative and artistic approach to cuisine. It's an unforgettable dining experience that perfectly caps off your first day in Chicago.

Bedtime

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4.69
Millennium Park
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4.61
Art Institute of Chicago
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Exploring Downtown Chicago

Morning

Begin your day with a stroll along Chicago Riverwalk. This scenic walkway offers stunning views of the city's architecture and is perfect for a morning walk or jog.

Afternoon

Visit Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city from one of its tallest buildings. Don't forget to step out onto 'The Ledge' for an exhilarating experience!

Evening

Enjoy dinner at Girl & The Goat, a popular restaurant known for its creative small plates and vibrant atmosphere.

Bedtime

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4.72
Chicago Riverwalk
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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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Cultural and Historical Highlights

Morning

Explore Field Museum, where you can learn about natural history through fascinating exhibits including Sue, the largest T. rex ever discovered.

Afternoon

Take a leisurely walk through Grant Park, often referred to as 'Chicago's front yard.' The park features beautiful gardens, sculptures, and plenty of space to relax.

Evening

Have dinner at Lou Malnati's Pizzeria, famous for its deep-dish pizza—a must-try when you're in Chicago.

Bedtime

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Field Museum
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4.70
Grant Park
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Entertainment and Relaxation

Morning

Visit Shedd Aquarium, home to thousands of aquatic animals from around the world. It's a great place to spend your morning learning about marine life.

Afternoon

Head over to Navy Pier for some fun activities including rides, shopping, and dining options along Lake Michigan.

Evening

End your trip with dinner at The Purple Pig, known for its Mediterranean-inspired dishes and extensive wine list.

Bedtime

Find amazing hotels in Chicago, Illinois.