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Roam Around

3 Days in Chicago Iconic Landmarks and Museums Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning

Start your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). This iconic landmark offers breathtaking views of the city from its observation deck. It's a great way to get an overview of Chicago's layout and major landmarks.

Afternoon

Head over to Millennium Park where you can see the famous Cloud Gate sculpture (The Bean) and enjoy the beautiful surroundings. For lunch, visit The Purple Pig, known for its Mediterranean-inspired small plates and vibrant atmosphere.

Evening

End your day with a visit to Chicago Riverwalk. This scenic walkway along the Chicago River is perfect for an evening stroll. For dinner, indulge in some deep-dish pizza at Giordano's, one of Chicago's most famous pizzerias.

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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Museums and Cultural Gems

Morning

Begin your day at the renowned Art Institute of Chicago. Spend a few hours exploring its vast collection of art from around the world. Afterward, grab a coffee at Intelligentsia Coffee located nearby.

Afternoon

In the afternoon, make your way to Field Museum. This natural history museum is home to Sue, the largest and most complete T. rex ever discovered. For lunch, head to Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.

Evening

Conclude your day with a visit to Chicago Theatre, an iconic venue known for its stunning architecture and rich history. Enjoy dinner at Girl & The Goat, a highly-rated restaurant offering innovative dishes.

Bedtime

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4.61
Art Institute of Chicago
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4.56
Field Museum
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Aquatic Adventures and Historic Sites

Morning

Start your morning with a trip to Shedd Aquarium, one of the largest indoor aquariums in the world. Explore its diverse marine life exhibits. Have breakfast or brunch at Wildberry Pancakes & Cafe nearby.

Afternoon

Next, head over to Adler Planetarium for an afternoon of stargazing and interactive exhibits about space exploration. For lunch, try some delicious BBQ at Smoque BBQ.

Evening

Wrap up your trip with an evening visit to Navy Pier, where you can enjoy various attractions including rides and restaurants. Dine at Au Cheval, famous for its burgers which are often considered among the best in America.

Bedtime

Find amazing hotels in Chicago, Illinois.