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Ultimate 5-Day Chicago Exploration Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and Sky-High Views
Morning
Begin your Chicago adventure with a hearty breakfast at Lou Malnati's Pizzeria, known for its deep-dish pizza. Afterward, take a stroll along the Chicago Riverwalk to admire the city's architecture and eventually make your way to the departure point for the Chicago River 1.5-Hour Guided Architecture Cruise. This informative cruise will provide a unique perspective of the city's famous buildings.
Afternoon
For lunch, head to The Purple Pig, a popular spot for Mediterranean flavors. Post-lunch, experience the thrill of standing on the glass-floored Skydeck Chicago at Willis Tower (Sears Tower), also known as The Ledge. Later, enjoy a leisurely visit to the Field Museum, where you can explore natural history and ancient cultures.
Evening
As the sun sets, dine at Gibsons Bar & Steakhouse, an iconic Chicago steakhouse. Afterward, take a walk along the Magnificent Mile, known for its upscale shops and vibrant atmosphere.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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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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Cultural Wonders and Scenic Views
Morning
Kick off the day with breakfast at Eataly Chicago, an Italian marketplace with a variety of dining options. Post-breakfast, visit the Art Institute of Chicago with a fast-pass ticket, allowing you to explore one of the oldest and largest art museums in the United States at your own pace.
Afternoon
For lunch, savor the flavors at Big Star, a trendy spot for tacos and whiskey. Afterward, enjoy a skip-the-line visit to the 360 Chicago Observation Deck for breathtaking panoramic views of the city and Lake Michigan.
Evening
Dine at Girl & the Goat, an award-winning restaurant known for its innovative menu. After dinner, take a relaxing walk in Millennium Park and don't miss the famous "Bean" sculpture, officially known as Cloud Gate.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.17360 Chicago Observation Deck
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4.17360 Chicago Observation Deck
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Historical Tours and Culinary Delights
Morning
Start with breakfast at Lula Cafe, a neighborhood favorite known for its creative dishes. Then, embark on the Chicago Prohibition Speakeasies Bus Tour or Walking Tour to learn about the city's history during the Prohibition era and visit hidden bars.
Afternoon
Enjoy a delightful lunch at Cafe Ba-Ba-Reeba!, offering a casual and lively atmosphere with authentic Spanish tapas. Post-lunch, take the Chicago Gangsters and Ghosts Guided Walking Tour to explore the city's notorious past and visit crime scenes and haunted spots.
Evening
Indulge in a sumptuous dinner at Au Cheval, famous for its upscale diner fare including the much-loved cheeseburger. Cap off the evening with a Windy City Ghosts Hauntings of Chicago tour to uncover the supernatural side of the city.
Bedtime
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4.90Chicago Prohibition Speakeasies Bus Tour or Walking Tour
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4.90Chicago Prohibition Speakeasies Bus Tour or Walking Tour
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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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Culinary Exploration and Navy Pier Fun
Morning
Start your day with a classic Chicago breakfast at Portillo's Hot Dogs, known for its hot dogs and Italian beef sandwiches. After breakfast, take a casual stroll at Navy Pier, exploring the shops and enjoying the lakeside views.
Afternoon
For lunch, head to Smoque BBQ to experience some of the best barbecue in the city. Post-lunch, visit the Chicago Museum of Science & Industry Ticket & Audio (ENG) to engage with the amazing exhibits and interactive displays.
Evening
Dine at Longman & Eagle, a Michelin-starred gastropub offering a wide-ranging menu. After dinner, you may choose to enjoy the vibrant nightlife in the Wicker Park neighborhood, known for its live music venues and eclectic bars.
Bedtime
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4.48Navy Pier
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4.48Navy Pier
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3.67Chicago Museum of Science & Industry Ticket & Audio (ENG)
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3.67Chicago Museum of Science & Industry Ticket & Audio (ENG)
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Final Day's Highlights and Farewell Dinner
Morning
Enjoy a leisurely breakfast at Kuma's Corner, a rock music-themed burger bar. Then, take a final walk through the city, visiting Marina City, also known as the "Corn Cob Towers," and the historic Tribune Tower.
Afternoon
For lunch, visit Pequod's Pizza to savor their famous caramelized crust deep-dish pizza. Afterward, take a guided tour of the The Chicago Theatre to learn about its rich history and architecture.
Evening
Conclude your Chicago journey with a memorable dinner at RPM Italian, offering modern Italian cuisine in an elegant setting. Reflect on your adventures as you enjoy your meal, and perhaps raise a glass to the Windy City.
Bedtime
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4.84Marina City
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4.84Marina City
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4.61Tribune Tower
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4.61Tribune Tower
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