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5-Day Chicago City and Lakefront Exploration Itinerary
Last updated: 2024 Jun 14City Icons and Skyline Views
Morning
Start your Chicago adventure with a classic Chicago-style breakfast at Miller's Pub, known for its hearty morning fare. After breakfast, take a stroll along the iconic Chicago Riverwalk to admire the city's architecture and vibrant riverfront.
Afternoon
For lunch, head to The Gage, a historic restaurant with a diverse menu. Post-lunch, visit the Art Institute of Chicago with a fast pass ticket to explore one of the oldest and largest art museums in the United States.
Evening
Enjoy a delightful dinner at City Social, offering panoramic views of the city. Cap off the evening with a visit to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for a breathtaking perspective of the Chicago skyline.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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Lakefront Serenity and Museum Marvels
Morning
Begin your day with breakfast at South Branch Tavern & Grille (The Loop - Chicago), a local favorite. Afterward, take a morning walk at the serene Navy Pier, enjoying the lakefront views and the iconic Centennial Wheel.
Afternoon
Have a leisurely lunch at Elephant & Castle before immersing yourself in the aquatic wonders of the Shedd Aquarium. Spend the afternoon exploring the diverse marine life and engaging exhibits.
Evening
Dine at Cindy's Rooftop, located in the heart of Chicago's Loop with a stunning view of Millennium Park. After dinner, take a relaxing evening stroll in the park and admire the famous Chicago Theatre sign.
Bedtime
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4.48Navy Pier
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4.48Navy Pier
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4.75Shedd Aquarium
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4.75Shedd Aquarium
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Historic Tales and Evening Cruise
Morning
Enjoy breakfast at Lockwood Restaurant & Bar before embarking on the Chicago Gangsters and Ghosts Guided Walking Tour. Explore the city's darker history and hidden stories.
Afternoon
Savor a delicious lunch at Bar Louie - Printers Row and then visit the Field Museum for an afternoon of natural history and cultural exhibits.
Evening
For dinner, experience the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise with a variety of dishes and stunning views of the city's architecture from the water.
Bedtime
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.56Field Museum
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4.56Field Museum
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Science, Sky, and Speakeasies
Morning
Start your day with breakfast at FireLake Grill House and Cocktail Bar. Afterward, visit the Chicago Museum of Science and Industry Ticket for an engaging morning of interactive exhibits and scientific wonders.
Afternoon
Have a satisfying lunch at Burger Bar Chicago and then soar to the Skydeck Chicago at Willis Tower (Sears Tower) to experience the Ledge, a glass balcony extending four feet outside the 103rd floor of Willis Tower.
Evening
Enjoy a unique experience with the Chicago Prohibition Speakeasies Bus Tour or Walking Tour, learning about Chicago's history during the Prohibition era. Conclude the evening with dinner at Sweetwater Tavern & Grille (Michigan Plaza - Chicago).
Bedtime
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4.61Chicago Museum of Science and Industry Ticket
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4.61Chicago Museum of Science and Industry Ticket
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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Architectural Marvels and Culinary Delights
Morning
Indulge in a delightful breakfast at Plymouth Restaurant & Rooftop Bar. Afterward, take the Chicago River 1.5-Hour Guided Architecture Cruise to witness the city's renowned skyscrapers and learn about its architectural history.
Afternoon
For lunch, head to LUXBAR for a sophisticated dining experience. Post-lunch, visit the Marina City to see the iconic "corn cob" towers and then explore the upscale shops along The Magnificent Mile.
Evening
Conclude your Chicago journey with a memorable dinner at City Social or 320 River Bar, both offering excellent cuisine and a vibrant atmosphere. After dinner, take a relaxing walk at Millennium Park and enjoy the famous "Bean" (Cloud Gate) sculpture.
Bedtime
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.84Marina City
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4.84Marina City
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