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Roam Around

3-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Chicago

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic green spaces. Here you can see the famous Cloud Gate sculpture (often referred to as 'The Bean'), and enjoy the serene Lurie Garden. For breakfast, head over to Au Cheval, renowned for its decadent breakfast options and highly-rated burgers.

Afternoon

In the afternoon, take a stroll along The Magnificent Mile, Chicago's premier commercial district. You can shop at high-end stores or simply enjoy the bustling atmosphere. For lunch, visit Giordano's for a taste of Chicago's famous deep-dish pizza.

Evening

End your day with an evening at House of Blues. This legendary venue offers live music performances that capture the essence of Chicago's vibrant music scene. For dinner, dine at The Publican, known for its hearty fare and communal dining experience.

Bedtime

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Cultural and Historical Highlights

Morning

Begin your day with a visit to the Art Institute of Chicago, home to an extensive collection of art from around the world. Afterward, enjoy breakfast at Eataly Chicago, where you can indulge in Italian pastries and coffee.

Afternoon

Spend your afternoon exploring Grant Park, often referred to as 'Chicago's front yard.' The park is home to Buckingham Fountain and offers beautiful views of Lake Michigan. For lunch, stop by Portillo's Hot Dogs for a classic Chicago-style hot dog.

Evening

In the evening, catch a game or concert at the iconic United Center. Whether it's basketball or hockey season or there's a major concert happening, this venue is sure to provide entertainment. For dinner, make reservations at Girl & the Goat, one of Chicago's most celebrated restaurants.

Bedtime

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Architectural Wonders & Local Flavors

Morning

Kick off your morning with a visit to A-Skydeck Chicago at Willis Tower (Sears Tower) . Enjoy breathtaking views from one of the tallest buildings in Western Hemisphere.

Afternoon

In afternoon explore more architectural marvels walk through Marina City then head over see Wrigley Field up close! Enjoy lunch nearby restaurant The Purple Pig known Mediterranean-inspired small plates.

Evening

Conclude trip evening stroll along Navy Pier . Enjoy rides games beautiful lakefront views Have dinner Bavette 's Bar & Boeuf offering classic steakhouse fare elegant setting.

Bedtime

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