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Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Magnificent Mile and Riverfront Marvels
Morning
Begin your Chicago journey with a bird's-eye view from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). After taking in the cityscape, enjoy a delightful breakfast at Cindy's Rooftop, known for its panoramic views and seasonal cuisine.
Afternoon
Immerse yourself in the upscale shopping and architecture of The Magnificent Mile. For lunch, savor the flavors of Chicago at The Gage, offering a menu inspired by the British Isles and France.
Evening
Take a leisurely stroll along the Chicago Riverwalk as the city lights up. Cap off the evening with a dinner cruise on the Chicago River with entertainment and a gourmet meal, experiencing the city's iconic skyline from a unique perspective.
Bedtime
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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Cultural Corners and Lakefront Wonders
Morning
Start with a visit to the renowned Art Institute of Chicago, home to a world-class collection. Enjoy a hearty breakfast at State and Lake Chicago Tavern, located in the heart of the Loop.
Afternoon
After the museum, take a short walk to the lush oasis of Millennium Park, where you can see the famous Cloud Gate sculpture. For lunch, head to South Branch Tavern & Grille (The Loop - Chicago) for a relaxed riverside dining experience.
Evening
Witness the grandeur of the Chicago Theatre and explore the vibrant entertainment district. Conclude the day with a serene evening at Adler Planetarium, followed by dinner at Lockwood Restaurant & Bar, known for its contemporary American cuisine.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.69Millennium Park
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4.69Millennium Park
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Lakeside Serenity and Historic Landmarks
Morning
Enjoy a peaceful morning at Lincoln Park & Zoo, one of the oldest zoos in the country. Grab a quick breakfast at Plymouth Restaurant & Rooftop Bar before exploring the park's attractions.
Afternoon
Visit the iconic Wrigley Building and then take a guided architecture tour to see the city's famous skyscrapers. For lunch, indulge in the classic Chicago experience at Miller's Pub, a historic spot with a traditional menu.
Evening
Relax with a scenic cruise on Lake Michigan, offering stunning views of the city's skyline. Dine at FireLake Grill House and Cocktail Bar, where you can enjoy dishes prepared with locally sourced ingredients.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.39Wrigley Building
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4.39Wrigley Building
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Parkside Pleasures and Museum Marvels
Morning
Begin with a refreshing morning at Grant Park, known as Chicago's "front yard." Grab breakfast at Staytion Market & Bar, offering a variety of options to start your day.
Afternoon
Spend the afternoon exploring the exhibits at the Field Museum and the Shedd Aquarium, both located within the Museum Campus. For lunch, head to Sweetwater Tavern & Grille (Michigan Plaza - Chicago) for a casual meal in a relaxed setting.
Evening
Conclude your museum day with a visit to the Soldier Field, an iconic sports and entertainment venue. Enjoy a dinner with a view at Randolph Tavern, where you can unwind and reflect on the day's discoveries.
Bedtime
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4.70Grant Park
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4.70Grant Park
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4.56Field Museum
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4.56Field Museum
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Architectural Icons and Culinary Delights
Morning
Delve into Chicago's architectural history with a guided tour of the Chicago Loop, featuring highlights like the Rookery Building and the Chicago Cultural Center. Enjoy breakfast at Reviver, known for its innovative dishes and stylish ambiance.
Afternoon
Experience the engineering marvel of the Marina City, also known as the "Corn Cob Towers." Then, take a break for lunch at Gilt Bar, an elegant spot offering a menu of refined comfort food.
Evening
Cap off your Chicago adventure with a visit to the Frederick C. Robie House, a masterpiece of the Prairie School architecture. Conclude with a farewell dinner at Bar Siena, where you can enjoy a taste of Italy in the heart of the city.
Bedtime
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4.83Chicago Loop
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4.83Chicago Loop
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4.73Rookery Building
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4.73Rookery Building
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