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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 a day of exploration! After breakfast, head to Millennium Park to see the famous Cloud Gate sculpture, also known as "The Bean." Take some time to walk around the park and enjoy the beautiful scenery.
Afternoon
For lunch, make your way to The Purple Pig, a popular restaurant known for its Mediterranean-inspired dishes. After lunch, take a stroll along the Chicago Riverwalk and admire the stunning architecture of the city. If you're interested in learning more about the city's architecture, consider taking a Chicago River Architecture Cruise.
Evening
End your day with a visit to The Magnificent Mile, a vibrant shopping district filled with luxury boutiques and department stores. Enjoy dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse known for its prime cuts of meat. After dinner, catch a show at the iconic Chicago Theatre.
Bedtime
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Museums and Landmarks

Morning
Start your day with a visit to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore the museum's extensive collection and don't miss iconic pieces like Grant Wood's "American Gothic." For a quick snack, grab a bite at Lula Cafe, a popular neighborhood cafe known for its delicious pastries.
Afternoon
After lunch, head to the Field Museum to learn about natural history and anthropology. Explore exhibits like Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered. For a unique experience, consider taking a Chicago Gangsters and Ghosts Walking Tour to learn about the city's history of crime and the paranormal.
Evening
Enjoy dinner at Au Cheval, a renowned restaurant known for its mouthwatering burgers. After dinner, take a leisurely walk along the Chicago River and enjoy the beautiful city lights reflecting on the water. End your evening with a drink at The Signature Room at the 95th, a rooftop lounge offering panoramic views of the city.
Bedtime
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Skyline Views and Aquarium Adventure

Morning
Start your day by visiting the 360 Chicago Observation Deck at the John Hancock Center. Enjoy breathtaking views of the city from the 94th floor. Afterward, grab a quick bite at Xoco, a Mexican street food-inspired restaurant known for its delicious tortas.
Afternoon
Head to the Shedd Aquarium for an underwater adventure. Explore the various exhibits and get up close to marine life from around the world. For a late lunch, indulge in some mouthwatering barbecue at Smoque BBQ.
Evening
End your day with a relaxing dinner cruise on Lake Michigan. Book a Chicago Lake Michigan Skyline Tour & Lake Hopper Cruise and enjoy a gourmet meal while taking in the stunning views of the city skyline. After the cruise, head to The Gage for a nightcap and enjoy the lively atmosphere of this popular gastropub.
Bedtime
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Exploring Evanston

Morning
Take a day trip to Evanston, a charming suburb located just north of Chicago. Start your day with a visit to the Bahá'í House of Worship, a stunning architectural masterpiece and a place of worship for the Bahá'í faith. Afterward, grab a delicious brunch at Yolk - South Loop.
Afternoon
Explore the beautiful campus of Northwestern University, known for its stunning architecture and picturesque surroundings. Take a walk along the shores of Lake Michigan and enjoy the peaceful atmosphere. For a sweet treat, stop by Bennison's Bakery and indulge in some freshly baked goods.
Evening
Enjoy dinner at Frontier, a rustic-chic restaurant known for its wild game dishes and craft cocktails. After dinner, catch a performance at the Cahn Auditorium, a historic theater located on the Northwestern University campus.
Bedtime
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Frank Lloyd Wright's Legacy

Morning
Take a day trip to Oak Park, a suburb located just west of Chicago and home to several Frank Lloyd Wright-designed buildings. Start your day with a guided tour of the Frank Lloyd Wright Home and Studio, where the famous architect lived and worked. After the tour, grab a quick bite at Cafe Ba-Ba-Reeba!, a Spanish tapas restaurant.
Afternoon
Explore the Oak Park neighborhood and visit other Frank Lloyd Wright-designed buildings, such as the Frederick C. Robie House and the Unity Temple. For a late lunch, head to Garrett Popcorn Shops and indulge in some Chicago-style popcorn.
Evening
End your day with a visit to the Ernest Hemingway Birthplace Home, the childhood home of the renowned author. Learn about Hemingway's early life and literary career. For dinner, enjoy Italian cuisine at Nando Milano Trattoria, a cozy restaurant known for its homemade pasta dishes.
Bedtime
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