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Roam Around

4-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic attractions. Marvel at the famous Cloud Gate sculpture (The Bean) and take a leisurely stroll through the beautiful gardens.

Afternoon

Head over to Art Institute of Chicago for an afternoon immersed in world-class art. This museum houses an extensive collection of artworks from various periods and cultures. For lunch, enjoy a meal at The Purple Pig, known for its delicious Mediterranean-inspired dishes.

Evening

End your day with a delightful dinner at Girl & the Goat, one of Chicago's most popular restaurants. Afterward, catch a live performance at Chicago Theatre, an iconic venue that hosts a variety of shows.

Bedtime

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Millennium Park
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Art Institute of Chicago
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Exploring Chicago's Landmarks

Morning

Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from the observation deck on the 103rd floor.

Afternoon

Take a walk along Chicago Riverwalk and soak in the scenic views of the river and city skyline. Stop for lunch at Portillo's Hot Dogs to savor some classic Chicago-style hot dogs.

Evening

In the evening, head to Navy Pier for some fun and entertainment. Enjoy dinner at RPM Italian, offering delicious Italian cuisine with stunning views of Lake Michigan.

Bedtime

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Skydeck Chicago at Willis Tower (Sears Tower)
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Chicago Riverwalk
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Cultural Gems and Historic Sites

Morning

Visit Field Museum in the morning to explore fascinating exhibits on natural history and culture. Don't miss Sue, the largest T. rex skeleton ever discovered.

Afternoon

Afterward, make your way to Adler Planetarium for an afternoon of stargazing and interactive exhibits about space exploration. Have lunch nearby at Giordano's, famous for its deep-dish pizza.

Evening

Conclude your day with dinner at Au Cheval, renowned for its mouthwatering burgers. Then head over to see some live music at House of Blues, where you can enjoy great tunes in an intimate setting.

Bedtime

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Field Museum
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Adler Planetarium
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Architectural Wonders and Local Flavors

Morning

Start your morning with a visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Take in panoramic views of the city from this iconic skyscraper.

Afternoon

Explore more architectural marvels by visiting Rookery Building, one of Chicago's most historically significant buildings designed by Frank Lloyd Wright. For lunch, try some tasty BBQ at Smoque BBQ.

Evening

Wrap up your day with dinner at Lou Malnati's Pizzeria for another taste of deep-dish pizza. Afterwards take a relaxing evening stroll through Grant Park

Bedtime

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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Rookery Building
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Final Day in Chicago

Morning

Begin your final day with a visit to Museum of Science and Industry. This museum offers a wide range of interactive exhibits that are both educational and entertaining. It's a great way to spend the morning exploring science and technology.

Afternoon

In the afternoon, head over to Lincoln Park & Zoo. This free zoo is home to a variety of animals and is located within the beautiful Lincoln Park. For lunch, enjoy a meal at The Publican, known for its farm-to-table cuisine and vibrant atmosphere.

Evening

Conclude your trip with dinner at Alinea, one of Chicago's most renowned fine dining establishments. After dinner, take a leisurely walk along Chicago River to soak in the city's stunning nighttime skyline.

Bedtime

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