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2 Days Exploring Chicago

2 Days Exploring Chicago Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning
Start your day with a visit to the iconic Millennium Park, home to the famous Cloud Gate sculpture (The Bean). This park is a must-see for its stunning architecture and beautiful green spaces. For breakfast, head over to Wildberry Pancakes and Cafe for some delicious pancakes and coffee.
Afternoon
In the afternoon, explore the Art Institute of Chicago, one of the oldest and largest art museums in the United States. The museum houses an extensive collection of art from around the world. For lunch, enjoy a meal at The Gage, known for its upscale pub fare.
Evening
End your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower) where you can enjoy breathtaking views of the city from one of the tallest buildings in the world. For dinner, dine at Girl & The Goat, a highly-rated restaurant known for its innovative dishes.
Bedtime
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Cultural and Historical Highlights

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 breakfast and try their famous donuts.
Afternoon
In the afternoon, explore Field Museum, home to millions of specimens including Sue, the largest T-Rex ever discovered. For lunch, head over to Lou Malnati's Pizzeria for some classic Chicago deep-dish pizza.
Evening
Conclude your trip with an evening at House of Blues where you can enjoy live music in an iconic venue. Before heading there, have dinner at RPM Steak for some exquisite steak dishes.
Bedtime
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