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![5-day trip to Chicago: Exploring Architecture, History, and Food](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018b8555-8365-7d4e-93c7-d06cb849aea1/location445.jpg)
5-day trip to Chicago: Exploring Architecture, History, and Food Itinerary
Last updated: 2024 Jun 14Discovering Chicago's Architecture
Morning
Start your day with a delicious breakfast at Lula Cafe in Logan Square. Afterward, embark on a Chicago River 1.5-Hour Guided Architecture Cruise to marvel at the city's stunning skyline and learn about its architectural history.
Afternoon
Head to the Art Institute of Chicago and explore its vast collection of artworks, including famous pieces like Grant Wood's "American Gothic" and Vincent van Gogh's "The Bedroom." For lunch, enjoy a delightful meal at The Purple Pig on Michigan Avenue.
Evening
Take a leisurely stroll along the Chicago Riverwalk and enjoy the scenic views. For dinner, indulge in a mouthwatering meal at Gibsons Bar & Steakhouse in the Gold Coast neighborhood.
Bedtime
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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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![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 Riverwalk in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
4.72Chicago Riverwalk
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Chicago Riverwalk
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History and Culture
Morning
Start your day with a visit to the Field Museum and explore its fascinating exhibits on natural history and anthropology. Grab a quick snack at Portillo's Hot Dogs before heading to the Shedd Aquarium to discover the wonders of marine life.
Afternoon
Immerse yourself in Chicago's history with a Chicago Gangsters and Ghosts 2-Hour Walking Tour. Afterward, satisfy your appetite with a late lunch at Au Cheval, known for its mouthwatering burgers.
Evening
Experience the vibrant atmosphere of Navy Pier and take a ride on the Chicago Navy Pier Centennial Wheel Regular & Express Ticket for breathtaking views of the city. Enjoy a delightful dinner at Eataly Chicago, where you can savor authentic Italian cuisine.
Bedtime
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![Visit Field Museum in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/16/53.jpg)
4.56Field Museum
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![Visit Field Museum in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/16/53.jpg)
Field Museum
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![Visit Shedd Aquarium in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/2e/46/94.jpg)
4.75Shedd Aquarium
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Shedd Aquarium
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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 and Ghosts 2-Hour 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 and Ghosts 2-Hour Walking Tour
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![Visit Chicago Navy Pier Centennial Wheel Regular & Express Ticket in Chicago](https://cdn.getyourguide.com/img/tour/05cb0a307913c9a4.jpeg/21.jpg)
4.43Chicago Navy Pier Centennial Wheel Regular & Express Ticket
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![Visit Chicago Navy Pier Centennial Wheel Regular & Express Ticket in Chicago](https://cdn.getyourguide.com/img/tour/05cb0a307913c9a4.jpeg/21.jpg)
Chicago Navy Pier Centennial Wheel Regular & Express Ticket
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Art and Sky-high Views
Morning
Start your day with a visit to the iconic The Bean (Cloud Gate) in Millennium Park. Explore the park and its beautiful gardens before heading to the Art Institute of Chicago for a guided tour of its world-renowned collection. Grab a quick bite at Big Star for a delicious Mexican-inspired brunch.
Afternoon
Soar to new heights at the 360 Chicago Observation Deck (Formerly John Hancock Observatory) and enjoy panoramic views of the city. For lunch, indulge in deep-dish pizza at Lou Malnati's Pizzeria.
Evening
Take a relaxing Chicago River Guided Sunset Cocktail & Architecture Tour and admire the city's stunning architecture while sipping on cocktails. End the day with a delightful dinner at Girl & the Goat, known for its innovative and flavorful dishes.
Bedtime
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![Visit Millennium Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
4.69The Bean (Cloud Gate)
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The Bean (Cloud Gate)
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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 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/a7/0e/e7.jpg)
4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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![Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/a7/0e/e7.jpg)
360 Chicago Observation Deck (Formerly John Hancock Observatory)
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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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Exploring Science and History
Morning
Start your day with a visit to the Museum of Science and Industry and immerse yourself in interactive exhibits and hands-on experiments. Grab a quick snack at Xoco before heading to the Chicago History Museum Admission Ticket to learn about the city's rich history.
Afternoon
Enjoy a leisurely lunch at Little Goat Diner, known for its creative twists on classic comfort food. Afterward, visit the 360 Chicago Observation Deck Sip and View Ticket for stunning views of the city while enjoying a refreshing drink.
Evening
Dive into Chicago's culinary scene with a Taste of Chinatown Food Walking Tour. Sample delicious Chinese dishes and learn about the neighborhood's history. For dinner, savor the flavors of authentic Chicago-style deep-dish pizza at Giordano's.
Bedtime
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![Visit Museum of Science and Industry in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/60/79.jpg)
4.31Museum of Science and Industry
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Museum of Science and Industry
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![Visit Chicago History Museum Admission Ticket in Chicago](https://cdn.getyourguide.com/img/tour/63d14ef6d83fa.jpeg/21.jpg)
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Chicago History Museum Admission Ticket
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![Visit Chicago 360 Chicago Observation Deck Sip and View Ticket in Chicago](https://cdn.getyourguide.com/img/tour/64931c418a3f9.png/21.jpg)
4.39360 Chicago Observation Deck Sip and View Ticket
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![Visit Chicago 360 Chicago Observation Deck Sip and View Ticket in Chicago](https://cdn.getyourguide.com/img/tour/64931c418a3f9.png/21.jpg)
360 Chicago Observation Deck Sip and View Ticket
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![Visit Chicago Taste of Chinatown Food Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/592711ee8891a.jpeg/21.jpg)
4.79Taste of Chinatown Food Walking Tour
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![Visit Chicago Taste of Chinatown Food Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/592711ee8891a.jpeg/21.jpg)
Taste of Chinatown Food Walking Tour
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Iconic Landmarks and Farewell
Morning
Start your day with a visit to the iconic Willis Tower Skydeck and The Ledge Ticket and step out onto the glass balconies for thrilling views of the city below. Grab a quick breakfast at Smoque BBQ for some mouthwatering barbecue.
Afternoon
Explore the vibrant shopping district of The Magnificent Mile and indulge in some retail therapy. For lunch, enjoy a delicious meal at Pequod's Pizza, known for its unique caramelized crust.
Evening
End your trip with a visit to the historic Chicago Theatre and take a The Chicago Theatre Marquee Tour to learn about its rich history. Enjoy a farewell dinner at Alinea, a renowned restaurant known for its innovative and artistic cuisine.
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 Ticket
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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 Ticket
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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 Chicago Theatre in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
4.71Chicago Theatre
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![Visit Chicago Theatre in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
Chicago Theatre
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![Visit The Chicago Theatre Tour Experience with Licensed Guide in Chicago](https://cdn.getyourguide.com/img/tour/d6ccfc9deae72735.jpeg/21.jpg)
4.73The Chicago Theatre Marquee Tour
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![Visit The Chicago Theatre Tour Experience with Licensed Guide in Chicago](https://cdn.getyourguide.com/img/tour/d6ccfc9deae72735.jpeg/21.jpg)
The Chicago Theatre Marquee Tour
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