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![3-Day Chicago Food, Tours, and History Extravaganza](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018f67f7-14b2-77c3-bd6d-220db0df0fcf/location751.jpg)
3-Day Chicago Food, Tours, and History Extravaganza Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and Deep Dish Delights
Morning
Start your day with a classic Chicago experience at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. After fueling up, head to the Willis Tower Skydeck and The Ledge to enjoy panoramic views of the city.
Afternoon
For lunch, savor the flavors of Chicago at Giordano's, another renowned spot for deep-dish pizza. Afterward, take a leisurely walk to The Magnificent Mile for some shopping and explore the nearby Wrigley Building.
Evening
In the evening, enjoy a sophisticated dining experience at The Signature Room at the 95th, offering stunning views of the city. After dinner, take a relaxing Chicago River 1.5-Hour Guided Architecture Cruise to see the city's famous buildings illuminated at night.
Bedtime
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![Visit Chicago Willis Tower Skydeck and The Ledge Ticket in Chicago](https://cdn.getyourguide.com/img/tour/4ef29da092a9da31.jpeg/21.jpg)
4.41Willis Tower Skydeck and The Ledge
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![Visit Chicago Willis Tower Skydeck and The Ledge Ticket in Chicago](https://cdn.getyourguide.com/img/tour/4ef29da092a9da31.jpeg/21.jpg)
Willis Tower Skydeck and The Ledge
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![Visit The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
4.65The Magnificent Mile
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![Visit The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
The Magnificent Mile
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![Visit Wrigley Building in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/81/cd.jpg)
4.39Wrigley Building
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![Visit Wrigley Building in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/81/cd.jpg)
Wrigley Building
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![Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/b4b30c0c6eccc80e.jpeg/21.jpg)
4.77Chicago River 1.5-Hour Guided Architecture Cruise
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![Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/b4b30c0c6eccc80e.jpeg/21.jpg)
Chicago River 1.5-Hour Guided Architecture Cruise
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Cultural Immersion and Gourmet Delights
Morning
Indulge in a delightful brunch at The Purple Pig, known for its Mediterranean-inspired dishes. Afterward, visit the Art Institute of Chicago to explore its world-class art collection.
Afternoon
For a unique experience, take a Chicago Architecture Boat Tour with Drinks to learn about the city's architectural history while enjoying a refreshing beverage. After the tour, have a late lunch at Girl & the Goat, a popular spot for creative cuisine.
Evening
Enjoy a memorable dinner at Alinea, a three-Michelin-star restaurant offering a multi-sensory tasting menu. Afterward, take a leisurely walk along the Chicago Riverwalk to end the night.
Bedtime
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![Visit Art Institute of Chicago in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/15/da.jpg)
4.61Art Institute of Chicago
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Art Institute of Chicago
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![Visit Chicago Architecture Boat Tour with Drinks in Chicago](https://cdn.getyourguide.com/img/tour/744f04dd251338c6.jpeg/21.jpg)
4.85Chicago Architecture Boat Tour with Drinks
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![Visit Chicago Architecture Boat Tour with Drinks in Chicago](https://cdn.getyourguide.com/img/tour/744f04dd251338c6.jpeg/21.jpg)
Chicago Architecture Boat Tour with Drinks
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![Visit Chicago Riverwalk in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
4.72Chicago Riverwalk
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![Visit Chicago Riverwalk in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
Chicago Riverwalk
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Historical Exploration and Culinary Delights
Morning
Start your day with a hearty breakfast at Au Cheval, famous for its indulgent dishes. Then, embark on a Chicago Gangsters & Ghosts Walking Tour to uncover the city's intriguing past.
Afternoon
For lunch, experience the vibrant atmosphere of Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs and Italian beef sandwiches. Afterward, visit the 360 Chicago Observation Deck for more stunning views of the city.
Evening
Conclude your Chicago adventure with a dinner at Gibsons Bar & Steakhouse, a beloved steakhouse in the city. After dinner, take a relaxing Chicago River Guided Sunset Cocktail & Architecture Tour to enjoy the city's skyline as the sun sets.
Bedtime
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![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
4.68Chicago Gangsters & Ghosts Walking Tour
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![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
Chicago Gangsters & Ghosts Walking Tour
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![Visit Chicago 360 Chicago Observation Deck General Admission in Chicago](https://cdn.getyourguide.com/img/tour/638fb05cb7c40.jpeg/21.jpg)
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![Visit Chicago 360 Chicago Observation Deck General Admission in Chicago](https://cdn.getyourguide.com/img/tour/638fb05cb7c40.jpeg/21.jpg)
360 Chicago Observation Deck
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![Visit Chicago River Guided Sunset Cocktail & Architecture Tour in Chicago](https://cdn.getyourguide.com/img/tour/4b8877882d559ae9.jpeg/21.jpg)
4.24Chicago River Guided Sunset Cocktail & Architecture Tour
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![Visit Chicago River Guided Sunset Cocktail & Architecture Tour in Chicago](https://cdn.getyourguide.com/img/tour/4b8877882d559ae9.jpeg/21.jpg)
Chicago River Guided Sunset Cocktail & Architecture Tour
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