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Roam Around

3-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic attractions. Here you can see the famous Cloud Gate sculpture (also known as 'The Bean') and enjoy the beautiful gardens and architecture. After exploring the park, head over to Lou Malnati's Pizzeria for a classic deep-dish pizza lunch.

Afternoon

In the afternoon, take a stroll along The Magnificent Mile, Chicago's premier commercial district. This bustling street is lined with shops, restaurants, and historic landmarks. Make sure to stop by Water Tower Place for some shopping and sightseeing.

Evening

End your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of the tallest buildings in the world. For dinner, indulge in a delicious meal at Girl & The Goat, known for its innovative dishes and vibrant atmosphere.

Bedtime

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Millennium Park
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4.65
The Magnificent Mile
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Cultural Gems and Scenic Views

Morning

Begin your second day with a visit to the renowned Art Institute of Chicago. This world-class museum houses an impressive collection of art from around the globe. Afterward, grab breakfast at The Purple Pig, where you can enjoy Mediterranean-inspired small plates.

Afternoon

In the afternoon, explore Chicago Riverwalk, a scenic promenade along the Chicago River. Take in the stunning architecture and maybe even hop on an architectural boat tour. For lunch, head to Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.

Evening

Spend your evening at Navy Pier, one of Chicago's top attractions. Enjoy rides, games, and entertainment while taking in views of Lake Michigan. For dinner, dine at Au Cheval, famous for its mouthwatering burgers.

Bedtime

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4.61
Art Institute of Chicago
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Chicago Riverwalk
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Historic Sites and Local Flavors

Morning

Start your final day with a visit to Field Museum, home to fascinating exhibits on natural history and culture. Afterward, have breakfast at Eataly Chicago , where you can savor Italian pastries and coffee.

Afternoon

In the afternoon, head over to Adler Planetarium for an immersive experience in astronomy and space science. For lunch, enjoy some BBQ at Smoque BBQ, known for its flavorful smoked meats.

Evening

Conclude your trip with an evening at the historic Chicago Theatre. Catch a show or simply admire its stunning architecture. For your final dinner in Chicago, treat yourself to a meal at Gibsons Bar & Steakhouse, renowned for its prime steaks and elegant ambiance.

Bedtime

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