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Chicago Adventure - 5 Days Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (often referred to as 'The Bean') and offers a beautiful green space in the heart of downtown Chicago.

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 extensive collection of artworks from around the world.

Evening

Enjoy dinner at Girl & the Goat, a highly-rated restaurant known for its innovative dishes and vibrant atmosphere.

Bedtime

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4.69
Millennium Park
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4.61
Art Institute of Chicago
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Exploring Chicago's Icons

Morning

Begin your day with a visit 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

Take a stroll along The Magnificent Mile, Chicago's premier commercial district. Enjoy shopping at high-end stores and exploring local boutiques.

Evening

Dine at Alinea, an award-winning restaurant renowned for its creative and avant-garde cuisine.

Bedtime

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Skydeck Chicago at Willis Tower (Sears Tower)
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4.65
The Magnificent Mile
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Cultural and Historical Treasures

Morning

Visit Field Museum, where you can explore fascinating exhibits on natural history, including Sue, the largest and most complete T. rex ever discovered.

Afternoon

Head over to Chicago Cultural Center, known for its stunning architecture and free art exhibitions. Don't miss the beautiful Tiffany dome.

Evening

Enjoy dinner at Joe's Seafood, Prime Steak & Stone Crab, famous for its delicious seafood and prime steaks.

Bedtime

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Field Museum
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Chicago Cultural Center
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River North Adventures

Morning

Start your day with a visit to Chicago Riverwalk. This scenic walkway along the Chicago River offers beautiful views of the city's architecture.

Afternoon

Explore Marina City, an iconic mixed-use residential-commercial building complex that is often referred to as 'the corn cob buildings.' Take some time to admire its unique design.

Evening

Have dinner at Portillo's Hot Dogs, a beloved Chicago institution known for its classic hot dogs and Italian beef sandwiches.

Bedtime

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Chicago Riverwalk
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4.84
Marina City
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Final Day of Exploration

Morning

Kick off your last day in Chicago with a visit to Adler Planetarium. This historic planetarium offers fascinating exhibits on astronomy and space exploration, along with stunning views of Lake Michigan.

Afternoon

Head over to Shedd Aquarium, one of the largest indoor aquariums in the world. Spend a few hours exploring its diverse marine life exhibits.

Evening

Conclude your trip with a memorable dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse known for its prime cuts and lively atmosphere.

Bedtime

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