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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Exploring the Windy City

Morning
Start your day with a delicious cup of coffee from Intelligentsia Coffee. Afterward, head to Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city. Don't forget to step out onto The Ledge for a thrilling experience.
Afternoon
Take a stroll along Navy Pier , where you can enjoy various attractions, shops, and restaurants. Grab lunch at The Purple Pig, known for its Mediterranean-inspired dishes and vibrant atmosphere. Afterward, take a relaxing cruise on the Chicago River to admire the city's stunning architecture.
Evening
Indulge in a memorable dinner at Girl & the Goat, an award-winning restaurant offering innovative American cuisine. Afterward, explore The Magnificent Mile , a renowned shopping district filled with luxury boutiques and iconic landmarks.
Bedtime
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Art and Culture in the City

Morning
Visit Millennium Park and marvel at Cloud Gate (The Bean) before exploring the nearby Art Institute of Chicago . Immerse yourself in world-class art collections and exhibitions.
Afternoon
Enjoy lunch at Au Cheval, famous for its mouthwatering burgers and indulgent comfort food. Afterward, visit the Field Museum to discover fascinating exhibits on natural history and anthropology.
Evening
Experience a live performance at the historic Chicago Theatre . Before or after the show, grab dinner at Wrigley Building , known for its stunning architecture and a variety of dining options.
Bedtime
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Discovering the Waterfront

Morning
Start your day with a visit to Shedd Aquarium , where you can explore diverse marine life. Afterward, head to Adler Planetarium for an immersive journey through space and astronomy.
Afternoon
Enjoy a scenic cruise on Lake Michigan and the Chicago River with the Chicago Architecture Center Cruise on Chicago's First Lady . Learn about the city's architectural gems while enjoying lunch onboard.
Evening
Take in panoramic views of the city from the 360 Chicago Observation Deck (Formerly John Hancock Observatory) . End your day with a romantic sunset cruise on Lake Michigan .
Bedtime
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Exploring Neighborhoods

Morning
Explore the vibrant neighborhood of Wicker Park and grab breakfast at a local cafe. Visit unique shops, art galleries, and street murals in this trendy area.
Afternoon
Head to Logan Square and enjoy lunch at one of its popular restaurants. Take a walk around the neighborhood to admire its historic architecture and visit local boutiques.
Evening
Experience the lively atmosphere of Lincoln Park. Enjoy dinner at a cozy restaurant followed by live music or comedy shows at one of the entertainment venues in the area.
Bedtime
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Farewell to the Windy City

Morning
Spend your last morning exploring Grant Park and Buckingham Fountain. Take a leisurely stroll along Lakefront Trail for beautiful views of Lake Michigan.
Afternoon
Indulge in a delicious brunch at a lakefront restaurant before visiting one last attraction of your choice, such as Museum of Ice Cream or Willis Tower Skydeck .
Evening
Take a scenic dinner cruise on Lake Michigan, enjoying stunning views of the city skyline as you savor a gourmet meal. Reflect on your memorable trip to Chicago before bidding farewell to the Windy City.
Bedtime
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