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4 Days of Fun in Chicago Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes and vibrant atmosphere. After breakfast, head over to Millennium Park, where you can marvel at the iconic Cloud Gate sculpture (The Bean) and enjoy a leisurely stroll through the park's beautiful gardens.
Afternoon
For lunch, make your way to Quartino Ristorante & Wine Bar, a charming Italian eatery offering a variety of small plates and an extensive wine list. Post-lunch, visit the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its impressive collection of artworks from around the world.
Evening
In the evening, enjoy dinner at The Capital Grille, renowned for its dry-aged steaks and elegant ambiance. After dinner, catch a live performance at the legendary Chicago Theatre, an iconic venue that hosts a variety of shows ranging from concerts to Broadway productions.
Bedtime
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Exploring Chicago's Rich History
Morning
Begin your day with breakfast at a local favorite spot before heading to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views of the city from one of the tallest buildings in the Western Hemisphere.
Afternoon
For lunch, dine at Avec, known for its Mediterranean-inspired dishes and cozy atmosphere. Afterward, take a short walk to visit The Magnificent Mile, Chicago's premier commercial district filled with shops, boutiques, and landmarks like the historic Water Tower.
Evening
In the evening, have dinner at Oriole, an upscale restaurant offering an exquisite tasting menu. Conclude your day with a visit to House of Blues for some live music in an intimate setting.
Bedtime
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Science and Nature Day
Morning
Kick off your morning with breakfast at another local cafe before heading to Field Museum. Spend several hours exploring this natural history museum's vast exhibits.
Afternoon
For lunch, try out some local flavors near Grant Park. Then make your way to Shedd Aquarium, where you can discover fascinating marine life through interactive exhibits and shows.
Evening
End your day with dinner at one of Chicago's top-rated restaurants before taking an evening stroll along Chicago Riverwalk. Enjoy stunning views of the city skyline reflected on the river.
Bedtime
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Cultural Immersion in Chicago
Morning
Start your final day with breakfast at another recommended spot before visiting Adler Planetarium. Dive into astronomy exhibits and enjoy panoramic views of Lake Michigan.
Afternoon
Have lunch nearby then head over to explore more cultural sites such as visiting either Lincoln Park Zoo or Navy Pier depending on preference; both offer unique experiences perfect for teens!
Evening
Wrap up your trip by dining at another highly-rated restaurant followed by enjoying some evening entertainment or simply relaxing back at River North reflecting on wonderful memories made during these four days.
Bedtime
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Adjacent Cities
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