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5 Days Exploring Chicago Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a visit to the iconic Millennium Park, where you can see the famous Cloud Gate sculpture (The Bean). This park is a must-see for first-time visitors and offers great photo opportunities.

Afternoon

Head over to the Art Institute of Chicago for an afternoon of exploring world-class art collections. This museum is one of the oldest and largest art museums in the United States.

Evening

Enjoy dinner at Lou Malnati's Pizzeria, known for its delicious deep-dish pizza. Afterward, take a leisurely stroll along the Chicago Riverwalk to enjoy beautiful views of the city skyline.

Bedtime

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4.69
Millennium Park
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4.61
Art Institute of Chicago
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Architectural Marvels and Local Flavors

Morning

Begin your day with a visit to the Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views from one of the tallest buildings in the Western Hemisphere.

Afternoon

Explore the historic Chicago Loop area and have lunch at Portillo's Hot Dogs, famous for its Chicago-style hot dogs and Italian beef sandwiches.

Evening

In the evening, head to House of Blues for some live music and entertainment. Enjoy dinner at The Purple Pig, which offers a variety of Mediterranean-inspired dishes.

Bedtime

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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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4.83
Chicago Loop
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Cultural Treasures and Scenic Views

Morning

Visit the fascinating exhibits at the Field Museum, one of the largest natural history museums in the world. Don't miss Sue, the largest T. rex ever discovered.

Afternoon

Take a relaxing walk through Grant Park, often referred to as 'Chicago's front yard.' For lunch, stop by Giordano's for another taste of Chicago's famous deep-dish pizza.

Evening

Spend your evening at Navy Pier. Start with dinner at Girl & The Goat, known for its innovative dishes. Afterward, enjoy various attractions like rides or simply take in views of Lake Michigan.

Bedtime

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Field Museum
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4.70
Grant Park
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Science Wonders and Historic Sites

Morning

Start your day with a visit to the interactive exhibits at the Museum of Science and Industry. This museum is perfect for all ages and offers hands-on experiences.

Afternoon

Head over to Lincoln Park & Zoo for an afternoon surrounded by nature and wildlife. For lunch, dine at Pequod's Pizza, known for its caramelized crust deep-dish pizza.

Evening

In the evening, enjoy a fine dining experience at Alinea, one of Chicago’s most acclaimed restaurants offering avant-garde cuisine.

Bedtime

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4.31
Museum of Science and Industry
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Final Day Highlights

Morning

Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning panoramic views of Chicago from above. It's a great way to start your final day in this vibrant city.

Afternoon

Explore The Magnificent Mile with its upscale shops and historic landmarks. Have lunch at Au Cheval, renowned for its burgers which are considered some of the best in America.

Evening

Conclude your trip with dinner at The Signature Room at 95th located atop John Hancock Center offering spectacular views along with fine dining.

Bedtime

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