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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Exploring the Windy City

Morning
Start your day with a delicious breakfast at Wildberry Pancakes and Cafe. Afterward, take a stroll along the Magnificent Mile and explore the luxury shops and boutiques.
Afternoon
Head to Millennium Park and visit Cloud Gate, also known as "The Bean." Take some iconic photos and enjoy the beautiful scenery. For lunch, try deep-dish pizza at Lou Malnati's Pizzeria.
Evening
Experience Chicago's vibrant nightlife by visiting Navy Pier. Enjoy dinner at The Purple Pig, known for its Mediterranean-inspired dishes. Afterward, take a ride on the Centennial Wheel for stunning views of the city.
Bedtime
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Architecture and Culture

Morning
Embark on a guided architecture cruise along the Chicago River. Learn about the city's famous buildings and architectural history. For breakfast or brunch, stop by Yolk for their delicious menu options.
Afternoon
Visit the Art Institute of Chicago and explore its extensive collection of artworks from around the world. Grab lunch at Cindy's Rooftop for panoramic views of Millennium Park.
Evening
Immerse yourself in Chicago's jazz scene by heading to Andy's Jazz Club. Enjoy live music performances while savoring dinner at Girl & the Goat.
Bedtime
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History and Entertainment

Morning
Take a tour of the historic Wrigley Field, home of the Chicago Cubs. Explore its iconic features and learn about baseball history. Grab a quick bite at Portillo's for their famous hot dogs.
Afternoon
Dive into Chicago's history with a Gangsters and Ghosts walking tour. Discover the city's dark past and visit infamous crime sites. For lunch, try the famous burgers at Au Cheval.
Evening
Enjoy a thrilling performance at The Second City, known for its improv comedy shows. Indulge in dinner at RPM Italian for delicious Italian cuisine.
Bedtime
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Lakefront Exploration

Morning
Start your day with a relaxing walk along the Lakefront Trail. Take in the beautiful views of Lake Michigan and enjoy the fresh air. Grab breakfast at Beatrix for their tasty brunch options.
Afternoon
Visit the Shedd Aquarium and explore its diverse marine life exhibits. Have lunch at The Gage, known for its upscale pub fare.
Evening
End your day with a sunset cruise on Lake Michigan. Experience breathtaking views of the Chicago skyline while enjoying dinner on board.
Bedtime
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Sky-high Views

Morning
Head to Willis Tower and visit the Skydeck for panoramic views of the city from above. Don't miss stepping out onto The Ledge for a thrilling experience. Grab breakfast or brunch at Little Goat Diner.
Afternoon
Explore the Museum Campus and visit the Field Museum to learn about natural history and anthropology. For lunch, try Xoco for their delicious Mexican street food.
Evening
End your trip with a visit to 360 Chicago Observation Deck. Enjoy stunning views of the cityscape while having dinner at Signature Room at the 95th.
Bedtime
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