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Roam Around

3-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and Local Flavors

Morning

Start your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). The Skydeck offers breathtaking views of the city from the 103rd floor. It's a perfect way to get an overview of Chicago's stunning skyline and landmarks.

Afternoon

After enjoying the views, head over to Millennium Park, where you can see the famous Cloud Gate sculpture (The Bean) and enjoy a leisurely walk through the park. For lunch, indulge in some deep-dish pizza at Lou Malnati's Pizzeria. This iconic Chicago eatery is known for its delicious and hearty pizzas.

Evening

In the evening, explore Navy Pier, one of Chicago's most popular attractions. Enjoy the rides, shops, and entertainment options available. For dinner, treat yourself to a meal at Girl & the Goat, known for its innovative dishes and vibrant atmosphere.

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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Cultural Gems and Culinary Delights

Morning

Begin your day with a visit to Art Institute of Chicago. This world-renowned museum houses an extensive collection of art from various periods and cultures. Spend your morning exploring its impressive exhibits.

Afternoon

For lunch, head to The Purple Pig, located on The Magnificent Mile. This restaurant is famous for its Mediterranean-inspired small plates. Afterward, take a stroll down The Magnificent Mile, where you can shop at high-end stores or simply enjoy the bustling atmosphere.

Evening

In the evening, catch a show at Chicago Theatre. This historic venue hosts a variety of performances ranging from concerts to Broadway shows. For dinner afterward, dine at Alinea, one of Chicago's most acclaimed restaurants offering an unforgettable culinary experience.

Bedtime

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4.61
Art Institute of Chicago
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4.65
The Magnificent Mile
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Aquatic Wonders and Historic Architecture

Morning

Start your day with a visit to Shedd Aquarium. This renowned aquarium features fascinating marine life exhibits that are sure to captivate visitors of all ages.

Afternoon

For lunch, head over to Portillo's Hot Dogs for some classic Chicago-style hot dogs. Afterward, explore the architectural marvels in downtown by visiting Rookery Building and taking in its stunning design.

Evening

Conclude your trip with an evening visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of the city as it lights up at night. For dinner on your last night in Chicago, savor a meal at The Signature Room at the 95th, located atop the John Hancock Center.

Bedtime

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