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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. Fuel up for the day ahead with their famous pancakes and specialty coffee. After breakfast, head to Millennium Park to see the iconic Cloud Gate sculpture, also known as "The Bean." Take some time to explore the park and enjoy the beautiful scenery.
Afternoon
For lunch, make your way to The Purple Pig. This Mediterranean-inspired restaurant offers a variety of small plates and delicious wines. After lunch, take a stroll along the Chicago Riverwalk and enjoy the views of the city skyline. If you're interested in architecture, consider taking a Chicago River Architecture Cruise to learn more about the city's famous buildings.
Evening
End your day with a visit to The Magnificent Mile, Chicago's premier shopping destination. Explore the various shops and boutiques, and enjoy dinner at The Signature Room at the 95th, a restaurant located on the 95th floor of the John Hancock Center. Indulge in delicious cuisine while taking in panoramic views of the city.
Bedtime
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Art and Culture in the City

Morning
Start your day with a visit to the Art Institute of Chicago. Explore the museum's extensive collection of art, including famous works by artists such as Van Gogh and Monet. Afterward, grab a quick bite to eat at Lula Cafe, a popular neighborhood spot known for its brunch menu.
Afternoon
After lunch, head to Navy Pier for some fun and entertainment. Take a ride on the Ferris wheel, enjoy the various attractions and activities, and grab a snack at one of the many food stands. If you're interested in marine life, consider visiting the Shedd Aquarium or the Adler Planetarium.
Evening
For dinner, make your way to Giordano's and indulge in their famous deep-dish pizza. After dinner, catch a show at the historic Chicago Theatre. Enjoy a night of live entertainment and immerse yourself in the city's vibrant performing arts scene.
Bedtime
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Exploring Chicago's Architecture

Morning
Start your day with a visit to the Chicago River. Take a stroll along the river and admire the city's impressive architecture. Afterward, grab a quick breakfast at Xoco, a Mexican street food-inspired restaurant known for its delicious churros and hot chocolate.
Afternoon
Join a Chicago River 1.5-Hour Guided Architecture Cruise to learn more about the city's architectural landmarks. After the cruise, head to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city. Enjoy lunch at The Gage, a gastropub located near Millennium Park.
Evening
For dinner, make your way to Au Cheval and savor their famous cheeseburger. After dinner, explore the vibrant nightlife of Chicago by visiting Wrigley Building and Marina City. These iconic landmarks offer a variety of dining and entertainment options.
Bedtime
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Exploring Evanston

Morning
Start your day with a visit to the Northwestern University. Take a walk around the beautiful campus and explore the various buildings and landmarks. Afterward, grab a coffee at Bourgeois Pig Cafe and enjoy a leisurely stroll through the charming streets of downtown Evanston.
Afternoon
For lunch, head to Edzo's Burger Shop and indulge in their delicious burgers and milkshakes. After lunch, visit the Mitchell Museum of the American Indian to learn more about Native American culture and art.
Evening
End your day with a relaxing dinner at Taco Diablo and enjoy their flavorful Mexican cuisine. After dinner, catch a performance at the Piven Theatre Workshop, a renowned theater company in Evanston.
Bedtime
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Discovering Oak Park

Morning
Start your day with a visit to the Frank Lloyd Wright Home and Studio. Explore the historic house and learn about the famous architect's life and work. Afterward, grab a quick breakfast at Bread & Wine and take a walk through the charming streets of Oak Park.
Afternoon
For lunch, head to Hemmingway's Bistro and enjoy their French-inspired cuisine. After lunch, visit the Oak Park Conservatory and immerse yourself in the beauty of the botanical gardens.
Evening
End your day with a visit to the Ernest Hemingway Birthplace Museum. Learn about the life and legacy of the renowned writer. For dinner, make your way to Mama Thai and savor their authentic Thai dishes.
Bedtime
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