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Roam Around

2 Days in Chicago Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning

Start your day with a visit to the iconic Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of the tallest buildings in the world. Afterward, grab a coffee and breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes and fresh ingredients.

Afternoon

In the afternoon, take a leisurely stroll through Millennium Park, home to the famous Cloud Gate sculpture. For lunch, head to Pizzeria Uno, where you can enjoy an authentic deep-dish pizza experience. After lunch, explore the fascinating exhibits at the Art Institute of Chicago, one of the oldest and largest art museums in the United States.

Evening

In the evening, enjoy a dinner cruise along the Chicago River with Odyssey Chicago River. This will give you a unique perspective of Chicago's stunning architecture while enjoying a gourmet meal. End your night with some live music at House of Blues, an iconic venue known for its vibrant atmosphere and great performances.

Bedtime

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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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4.69
Millennium Park
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Cultural Gems and Lakeside Fun

Morning

Begin your second day with a visit to The Magnificent Mile, a bustling shopping district filled with high-end stores and boutiques. Stop by Stan's Donuts & Coffee for a sweet treat and coffee to fuel your morning shopping spree.

Afternoon

Afterward, head over to Navy Pier for some lakeside fun. Enjoy various attractions including rides, shops, and restaurants. For lunch, dine at Giordano's on Navy Pier for another taste of Chicago's famous deep-dish pizza. Post-lunch, visit the Shedd Aquarium to explore its diverse marine life exhibits.

Evening

Conclude your trip with an evening visit to Adler Planetarium. Experience their impressive sky shows and interactive exhibits about space exploration. For dinner, savor some fine dining at The Signature Room at the 95th located in 875 N Michigan Ave (formerly John Hancock Center), offering panoramic views of Chicago's skyline.

Bedtime

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