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Roam Around

2-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Chicago

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 beautiful gardens and public art installations. It's a great way to immerse yourself in the city's vibrant culture.

Afternoon

After exploring Millennium Park, head over to Art Institute of Chicago. This world-renowned museum houses an extensive collection of art from various periods and cultures. Plan to spend a few hours here as there's so much to see. For lunch, enjoy a meal at The Purple Pig, known for its Mediterranean-inspired small plates.

Evening

In the evening, take a stroll along Chicago Riverwalk. The Riverwalk offers stunning views of the city's architecture and is perfect for a leisurely walk. For dinner, indulge in some classic Chicago deep dish pizza at Lou Malnati's Pizzeria.

Bedtime

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Architectural Wonders and Local Flavors

Morning

Begin your second day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of its tallest buildings. Afterwards, grab breakfast at Au Cheval, famous for its delicious brunch options.

Afternoon

Next, explore the architectural marvels by visiting Rookery Building and then take a guided tour through Chicago Pedway, an underground network that connects many of the city's landmarks. For lunch, head over to Girl & the Goat, known for its innovative dishes.

Evening

Conclude your trip with an evening visit to Navy Pier, where you can enjoy various attractions including rides and shops. For dinner, savor some seafood at Joe's Seafood, Prime Steak & Stone Crab.

Bedtime

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