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Roam Around

Chicago Adventure 2 Days Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic attractions. Here you can see the famous Cloud Gate sculpture (often referred to as 'The Bean'), enjoy the serene Lurie Garden, and take in the beautiful architecture of the Jay Pritzker Pavilion. After exploring the park, head over to for a delightful breakfast to fuel up for the day.

Afternoon

In the afternoon, take a stroll along Chicago Riverwalk. This scenic waterfront path offers stunning views of the city's skyline and is perfect for a leisurely walk or bike ride. You can also stop by some of the charming cafes and shops along the way. For lunch, visit , which is known for its delicious local cuisine and great ambiance.

Evening

End your day with an exciting visit to House of Blues. This legendary music venue hosts live performances from top artists across various genres. Enjoy dinner at , located nearby, where you can savor some mouth-watering dishes while soaking in the vibrant atmosphere.

Bedtime

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Chicago Riverwalk
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Cultural and Historical Highlights

Morning

Begin your second day with a trip to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Here you can explore an extensive collection of artworks from around the world. Afterward, grab breakfast at , a highly-rated spot known for its fantastic morning offerings.

Afternoon

In the afternoon, visit Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views from one of the tallest buildings in North America. Don't forget to step out onto 'The Ledge' – a glass balcony extending four feet outside the 103rd floor! For lunch, head over to for some delicious eats.

Evening

Conclude your trip with an evening at Navy Pier. This popular destination offers entertainment options such as rides, shops, and restaurants. Enjoy dinner at , which provides excellent food with a view of Lake Michigan.

Bedtime

Find amazing hotels in Chicago, Illinois.